Interview with Ryan Winkler, Candidate for Minnesota Attorney General

Ryan Winkler is running for Minnesota Attorney General in 2018. I’ve known Ryan since my last year of law school at the University of Minnesota. I had just started one of the first student chapters of the American Constitution Society, and Ryan was starting one of the first chapters for practicing lawyers.

Soon after, Ryan entered the Minnesota House of Representatives as a DFLer from Golden Valley, and served from from 2007 to 2015. In 2015 he left the legislature to support his wife’s career when she took a job in Belgium. Since then, Ryan has been going back and forth between Belgium and Minnesota, and he will obviously move back in time for his campaign.1

I haven’t kept in touch with Ryan since I graduated law school, but I saw him do plenty of good work in the Minnesota legislature. And since it is really early in the 2018 race, I thought it would be a good opportunity to reconnect and interview Ryan.

We spent about an hour talking about what a Minnesota Attorney General does and what kind of attorney general Ryan intends to be, including how he would use the office to prevent the wealthy (and others) from hiding behind “wall of privilege.” We discussed the role the Minnesota Attorney General could play in resolving complaints like those of the Black Lives Matter movement, and how a state attorney general could stand up to unconstitutional actions by the federal government under President Trump.

Trancript

Sam Glover: Hi, Ryan. Welcome to the very first Caveat Emptor interview/podcast/thing. I’m really excited to have you here. As a disclaimer, I should probably start out by saying that I am supporting Ryan for his contingent campaign for attorney general, and so this is a friendly interview. I don’t want people to get the wrong idea that I’m trying to plant this. Ryan and I, we met each other in 2002 or 2003, when you started the American Constitution Society for Law and Policy chapter for practicing lawyers in the Twin Cities.

Ryan Winkler: Yeah, a catchy name.

Sam Glover: Yeah. ACS now, we use. Do you remember what led you to found that ACS chapter way back then?

Ryan Winkler: Yeah, it was pretty simple. It was in the aftermath of Bush V. Gore. The conservative movement, for a long time, had weaponized the courts as a very activist judiciary. Of course, in law school, you become well aware of the Federalist Society.

You have George W. Bush beginning to look for justices and judicial appointments, and having a deep bench to turn to of people who had been involved in the Federalist Society one way or the other, and I just wondered, why isn’t there a liberal version of what the conservatives are doing? I found out that there was one that had just started, and decided I would get going and see what we could do in founding a chapter.

Sam Glover: That was really early on. I think ACS was only a year or two old at that point.

Ryan Winkler: Yeah, I think so. There weren’t very many people to talk to at the office in DC.

Sam Glover: Yeah. I think this was the third lawyer chapter that you had opened, and it’s still going strong. I was looking at some of their recent activities, they’re still out there and doing stuff—so, well done.

Ryan Winkler: Yeah. They’re making the early founders look pretty bad.

Ryan Winkler’s Path to Politics

Sam Glover: Absolutely! I’m curious, does that experience of founding ACS, the motivations that brought you there, is that what led you into politics?

Ryan Winkler: I would say that the things that brought me into politics were the things that brought me into ACS to begin with. I had a long interest in public affairs and politics and policy. In fact, my parents, I don’t know if this is true, I have a hard time believing it’s true, but they claim that I explained to my sister what homestead property taxes are when I was four and she was ten.

Sam Glover: That sounds like family lore.

Ryan Winkler: It could be true. I’ve had a longstanding interest in those things, and I guess just always had a sense of the kind of community I thought we should have, the kind of place I wanted to live in, a sense that people before me had made a lot of sacrifice and made a lot of good decisions to build a state and a city, or a small town where I grew up, where people could get ahead through hard work and doing the right thing. I have always felt like anybody who stands in the way of that needs to be put back in their place, and those basic values need to be the things that are guiding our policy and our politics. As a new lawyer, ACS was a chapter of that, and eventually the legislature was another.

Sam Glover: You were a baby lawyer when you founded ACS. How long did you end up practicing before you joined the legislature?

Ryan Winkler: I spent about three years at a small firm called Smith Parker, and it was a firm that represented watershed districts, the metropolitan council, it did public-private partnerships in Indianapolis to help neighborhoods facing challenges, coordinated investments from public and private sources, and some just straight litigation. I did a range of things. I was interested in the public nature of that firm. I did that for about three years, and then I went in-house at a software company. While I was at the software company, the legislative seat, where I lived, opened up, and I ran for the legislature and stayed in the legislature in Minnesota as part-time.

I spent the winter and spring at the legislature, and then I spent the rest of the year in a business setting at a software company first, and now at a company that’s developing a cancer drug.

Sam Glover: You had a range of experiences as a lawyer. You did some litigation, you did some public work, you did some business work, and then you went to the legislature. Maybe you could talk about, as you look at your legislative career, what were your signature initiatives? What are you most proud of that you were able to accomplish during that time?

Highlights at the Legislature

Ryan Winkler: The two highlights for me, well, there’s 2.5 maybe. The first one in my first year at the legislature was when the 35W bridge collapsed. It was a number of years after, but the example of the 9/11 fund was on people’s mind. I proposed a victim compensation fund to help victims of the bridge collapse deal with their lost income, medical expenses—all the things that go into the way that your life is disrupted after the bridge collapsed. I put that proposal forward, and ultimately, through a long struggle at the legislature, got that enacted, and a year later, every single bridge victim had accepted their award amount and had waived their right to sue the state, and the state, then, could pursue the private contractors to get some recovery of those funds, and the victims also could pursue them.

We made sure that those bridge victims were not left waiting while the court system figured things out, or while the political process played itself out. It worked extremely well. I was a first-year legislature when I did it.

Sam Glover: Right.

Ryan Winkler: That was a good way to start. The final big thing that I worked on that I’m probably equally or more proud of is the minimum wage bill in Minnesota. In part, that was interesting because we had democrats in charge of the House, Senate and governor’s office, but when we first tried to pass a bill, we couldn’t get agreement on anything above about $7.50 an hour, which was really very inadequate. We had to, basically, say, “No, we’re not going to take that deal.” Walk away until the next legislative session a year later, and in the meantime, worked with a labor faith and nonprofit organizations to very heavily persuade the holdouts on a stronger minimum wage bill.

Sam Glover: $7.50, that’s not a real thing, right? I mean, that’s not a real amount of money.

Ryan Winkler: That’s what the proposal was from many of my democratic colleagues.

Sam Glover: That’s amazing.

Ryan Winkler: We fought, basically, democratic legislatures in order to get a stronger bill, which ended up being $9.50 an hour, an index for inflation thereafter. At the time, that was one of the top three minimum wage laws in the country, as far as how high the number went. Of course, events have changed since that time, but the reason why we wanted an index to inflation was we wanted to create a rising floor on wages that wouldn’t require these same activists and organizations to go back and fight for it all the time. Instead, allow us to move on to things like paid family leave, earned sick leave, affordable childcare, all the things that are required to actually make a service sector job pay enough to potentially, at least, support a family, or support an individual.

Sam Glover: What’s the .5?

Ryan Winkler: The .5, I was reminded of this yesterday, and that’s when Governor Pawlenty illegally, unconstitutionally used his authority to un-allot state spending.

Sam Glover: Oh, yeah.

Ryan Winkler: I convinced my colleagues to hire David Lillehaug to file an amicus brief and join the suit against the governor for that, and we prevailed.

Sam Glover: Another ACS member, I think.

Ryan Winkler: David Lillehaug, yes.

Sam Glover: Yeah.

Ryan Winkler: David was one of the people who helped sponsor the chapter when we got going.

Sam Glover: That’s right. I guess I’m just going to keep bringing it back to that. Okay. Now we’ve got a picture of your background. More recently, I think your wife got a job overseas and you decided to take a break?

Moving to Belgium

Ryan Winkler: Yeah. In the summer of 2015, there was a job opportunity for Jenny, my wife, to be general council for Carlson Hotels operations in Europe, and so I resigned from the legislature and moved to Belgium, and will be moving back again this summer after two years break. I have the nontypical path to statewide office in Minnesota, which is by moving overseas first.

Sam Glover: I think you may be one of the only ones who’ve done it that way. Okay. Very cool. I wanted that overview because I’m curious. When you look back at that, how do you think those experiences help us figure out what kind of an attorney general you would be?

Ryan Winkler: I think if you asked people at the legislature what kind of legislature I was, they would probably say that I was someone who was willing to speak up, work hard, fight hard for the things that I believed in. I was willing to take on people in my own party, if necessary, to get things done on behalf of what I thought the public needed, and I was certainly willing to take on the other party if I felt like they were mishandling their responsibility and doing the wrong thing. People, I think, would say that I have the guts to actually speak the truth as I see it and put everything on the line in order to get the job done.

Sam Glover: It strikes me, and one of the reasons that we’re supporting you is what I know about the work that you’ve done is you’ve tried to represent what you think is right for Minnesotans.

Ryan Winkler: That shouldn’t be a noteworthy observation.

Sam Glover: No, I get that, but noticing that someone walks the walk as well as talking the talk is an important thing, and I think you have walked the walk in a number of different ways. You stick up for the little guy, but you stick up for the middle guys, and everybody, and I think that’s really important. Politicians always talk about, “I represent all of my constituency,” whether it’s the president talking about, “I represent all Americans,” or Minnesota politicians saying, “I represent all Minnesotans,” but the attorney general is a different kind of a job, in which you actually do represent them. Minnesotans are your actual clients.

Ryan Winkler: Right.

What Does the Attorney General Even Do, Anyway?

Sam Glover: It’s very different than the typical, “Oh, of course I represent you, but I’m really going to pursue policies and things,” but an attorney general, their job is to actually bring lawsuits on behalf of the people. Maybe we should pick up and talk about, what is the job? What does the AG actually do, because it’s not the big sexy governor job, and so I think it might fly under a lot of people’s radars. What is it?

Ryan Winkler: As you said, the first job of the attorney general is to represent the interest of the people, and the state, and the land, and the resources of the state in court. That’s a very broad mission. The attorney general is elected statewide every four years and has a great deal of discretion in deciding what ultimately is the most important public interest involved in what’s going on in court, what policies may come out of Washington that may affect Minnesota, what private interests may be doing that could affect the public interest in Minnesota. There’s a great deal of discretion. Ultimately, if an attorney general doesn’t adequately or correctly represent the interest of the public in the state, then the voters have a check on that every four years.

There’s a great deal of discretion bounded by a statewide election. The office itself is interesting for a lawyer and interesting for me because its authority does not just come from the state constitution or state statute, unlike other offices. The attorney general actually was an office in colonial times and had standing in the common law to represent the public interest. That common law foundation for the authority of the office to represent the public interest—parens patriae—is still recognized in the courts.

In fact, a big component of the tobacco litigation in the 1990s was a reaffirmation in the court system that attorney general had independent authority to bring lawsuits on behalf of the public interest, regardless of what state law or the state. Obviously, law in constitutions can aggregate that authority, but it is an inherent power of the office.

Sam Glover: That seems totally consistent with the nature of the attorney-client relationship in general, which is, and here I’m going to get a little geeky because I’m a lawyer and you’re a lawyer.

Ryan Winkler: And who’s listening to your podcast?

Sam Glover: Yeah, that’s right.

Ryan Winkler: Yeah.

Sam Glover: Lots of people think it’s their lawyer’s job to do what they want, but it’s not. It’s the lawyers job to do what’s in your best interest in view of what your goals for the representation are. It sounds like the attorney general’s common law origins and statutory origins preserve some of that independence. It’s a different goal than just doing what Minnesotans want. It’s what’s doing what’s best for Minnesotans.

Ryan Winkler: Of course, if the public strongly disagrees, they have the power to get rid of them.

Sam Glover: You can always fire your lawyer.

Ryan Winkler: The legislature and the governor strongly disagree, they could, in theory, cut the budget of the office, or in some way pass statutes constraining the attorney general’s authority. All of these things are bounded in a practical way by politics in the democratic process, but as a matter of legal authority, it’s there. In addition, all of the attorneys in the office serve at the pleasure of the attorney general. They’re all political appointments. There’s a tremendous amount of discretion that the attorney general has to decide what issues to take up, what causes are important, and there are some statutory obligations as well, but there is a lot of discretion.

On the statutes side, you do represent state agencies in court. The attorney general’s office in Minnesota does have a role in prosecuting cases where a local county attorney has a conflict of interest or is, in some way, unable to bring that case. They have a role of handling appeals in criminal cases on behalf of county attorneys. Then the consumer fraud statutes grant the attorney general tremendous power.

Sam Glover: Which is, of course, what I’m most familiar with, but yeah.

Ryan Winkler: That’s often what you hear about. You hear about a state attorney general getting settlements from businesses that have defrauded people or debt collectors on behalf of hospitals that are using practices that are pretty shady. There’s all sorts of ways that people abuse their economic power, and the attorney general, traditionally in consumer fraud type issues, has been the leader.

How to Choose an Attorney General

Sam Glover: Especially in Minnesota. With the common voter, what things should they be taking into consideration to vote for the attorney general?

Ryan Winkler: I would put it pretty simply, which is if you are a powerful person, if you have a corporation behind you, if you are rich, if you are the representative of a big organization in some way and have a lot of leverage, you have all the resources that you need to be an advocate for yourself in the legal system. I think the people of the state should look at which person they think is best going to advocate for them in the legal system, regardless of who’s on the other side. I think independence and a proven dedication to justice are the things that they should look for. It’s not going to be a resume. It’s going to be a sense of who the person is and what drives their character.

Sam Glover: I guess it’s maybe a little bit like many clients want a lawyer who they feel like believes in them and will fight for them.

Ryan Winkler: Everyone wants a bulldog.

Sam Glover: Yeah. I don’t think a bulldog is the right lawyer for everyone, but I think it’s that same sense of, “I want somebody who’s going to fight for me.”

Ryan Winkler: Yeah. Somebody who’s going to be a tenacious fighter on my behalf.

Sam Glover: I suppose most people come into contact with the attorney general through the complaint process, really. I have a problem, and it feels like a consumer problem, or a justice problem, or a racial problem, or a discrimination problem, and I want to let the AG know about it. That can sometimes feel like the cold administrative process. I happen to know that behind the scenes, it’s not.

People are looking at those and saying, “Does this signify a larger problem? Should we be shining a light on this? Should we be investigating it?” Usually, by the time the AG takes action, it’s like showing up with a cannon to a knife fight.

Ryan Winkler: Right.

Sam Glover: You want somebody who you can trust to be an administrator who is actually paying attention to those sorts of little contacts, I think.

Ryan Winkler: Yeah, I think that’s important. You have to then, also, hope that they will have the very talented and able people working in the office because it’s not a cold bureaucratic exercise. Every day, it’s a question of what cases, what problems rise to the top that demand our attention because you can’t do everything. You want people who are able to leverage their ability as much as possible, but also who have a sense of what issues that are coming across our desk today are the ones that are going to be most important and help the most people.

Ryan Winkler’s “Contingent Campaign”

Sam Glover: Yeah. We’ve talked about the office and how to decide. I haven’t yet let you say what I think you want to say, which is that you are running a contingent campaign.

Ryan Winkler: Well, that is true.

Sam Glover: Which is a little bit unusual.

Ryan Winkler: We have a very able incumbent attorney general, Lori Swanson of Minnesota, who has served a number of terms and done very well. People believe that she is likely to be a candidate for higher office in Minnesota in 2018, and she has not yet formally announced that. My announcement of a campaign for attorney general is premised on the notion that she will be running for a higher office and not seeking reelection as attorney general. I am not challenging her, but I am trying to get geared up and ready to go as early as possible in order to be ready to run and win, and put together a really strong campaign in the likely event that she decides to do something else.

Sam Glover: Yeah. There’s not a whole lot of doubt surrounding her running for governor at this point, although it’s very early on. We’re two years out, essentially, but I suppose I wanted to make sure to clarify that.

Ryan Winkler: Right. I think it’s important. There are not certainties in politics or in life, so you always have to take your chance and put in the effort where you think the outcome is likely to be the best, so that’s what I’m doing.

Sam Glover: Let me ask, what would you do if she decided not to? Where would you take your political ambitions?

Ryan Winkler: I don’t know that I would immediately be a candidate for anything else. I don’t have any backup plans, or anything like that. It wouldn’t be harmful to go back into private practice and earn a living doing better than what you can in public service, which isn’t bad, but it’s, of course, an option. It’s possible, and I’ll deal with that when it happens. It’s a little bit similar to when I first ran for the legislature.

The filing for office is in July and the primary was in the beginning of September. It was about ten weeks total. On the last day, my state representative ran for state senate, and my state senator ran for attorney general, and so it all happened in the blink of an eye, and I had to make a decision within a couple of hours whether to do it, and then once I was in, I got a good memo from a mentor of mine saying that in order to win this race against two opponents who had a track record in local politics already, which I did not, in order to win, I was going to have to come up with $20,000 of my own money and put it in the race. I took a second mortgage out on my house, got the money, spent it on literature and mail, a mail program, and just managed to beat both of the other two candidates.

If I hadn’t moved quickly and taken that risk, it wouldn’t have happened. There’s lots of ways to spend your life, and if you’re going to be in politics, and there’s a campaign, I’m ready to go all in, even knowing that the outcome is never certain.

Money and Politics

Sam Glover: You know what’s interesting to me? I have not been all that engaged and involved. I’ve been engaged in politics, in the sense that I pay attention to the news, I vote for people, but I haven’t really learned all that much about how politics works until recently. Often, people talk about the money in politics, and what I think is really interesting, what I’ve been learning recently, is most of that money goes towards pizza, fliers, maybe ads.

You think, “Oh, this person donated $1,000 to somebody’s campaign,” and that sounds like, “Oh, my God, they must’ve bought them off.” It’s not going into their pocket. They’re turning around and spending it on totally mundane things, like putting pizza and coffee into volunteers so they can go out and have conversations with people.

Ryan Winkler: There is a certain economic irrationality to the whole thing where I spend months trying to bring money in the door, that you raise a million dollars to get a job that pays $100,000 a year. If you spent that much time working and building a business, the personal benefits would probably be a lot higher than what you get in politics.

Sam Glover: Which is to say you have to be very motivated to try and do what the job requires, which is it’s a service job.

Ryan Winkler: It is a service job. Yeah. Obviously, there are plenty of other benefits that come that aren’t financial. People’s motivations vary. In my observation, some people simply like the status and they feel powerful, and it’s probably the best job they can get. Other people have a real sense of mission and service.
Other people have a love of public policy and like to be involved in working on issues. For some people, it’s a combination of things.

Sam Glover: I guess there’s hundreds of people in the legislature and in public service, so of course, it varies.

Ryan Winkler: Right. There is money in politics and it certainly can be corrupting, and it is, but money, it’s a proxy for power. When we talk about a lot of money in politics coming from certain people, what we’re really saying is that they have more power than other people do. They have a power to influence the outcomes that other people don’t. That’s why we always have to be vigilant and, I think, try to tell the truth about what’s going on, who’s behind it, and who’s benefiting from it.

“Walls of Privilege”

Sam Glover: That’s a perfect segue. I went to a fundraiser, and maybe one of your first fundraisers, several weeks back, and you talked about using the attorney general’s office to prevent the wealthy from hiding behind their walls of privilege, which are built by power and built by the money that builds that power. I’d like you to explain a little bit more about what you mean by that. Particularly, that phrase “walls of privilege”.

Ryan Winkler: Yes. I wouldn’t just say it’s the wealthy, I think it’s anybody with a position of influence tends to have a desire to create rules that will allow life to be easier for them, to the detriment of others. A successful business often will, especially a big one, can go to the legislature, get favorable rules or laws created, which makes it easy for them to succeed, and for competing businesses, or new businesses, to compete with them and try to take them on. I think net neutrality was an example of that. That’s just a straight up business proposition. This isn’t about the rich specifically, this is about a well entrenched, very large set of businesses who want to hold on to their spot and don’t want to openly compete with others.

Sam Glover: Right. On behalf of the telecoms, they just want to make more money.

Ryan Winkler: Yes.

Sam Glover: They want to find new ways to charge people for things.

Ryan Winkler: Absolutely. They want to bring in more money. That’s the original idea behind antitrust. It was in part, but it wasn’t always just about consumer prices. It was also about reducing the amount of power that any economic entity, any firm would have in a market segment so that others could come in and compete fairly with them. It was, in a way, a democratic instinct in the notion that any person should be able to enter the marketplace if they have a good idea and can find capital to do it, and so you shouldn’t be holding it back. That’s what I mean, in part, by walls of privilege.

You see that in employment arraignments. For example, this is an example of what the New York attorney general recently did. He sued Domino’s Corporate in together with six franchisees because the six franchisees had illegally misclassified their delivery drivers as independent contracts instead of employee, thereby denying them minimum wage, over time, other kinds of benefits that go with being an employee. Typically, you would say, “Well, the employment relationship is between the franchisee and the driver, and Domino’s Corporate has nothing to do with it.” That is a legal arraignment, which the law has through statute and favorable court decisions, over time, has allowed companies to take the profits out of the business, but evade responsibility for the practices of the small operators, and then, of course, limit what the depths of their pockets on these for recovery, and so forth.

What the New York attorney general did is sue Domino’s, as well, on a joint employment theory, basically stating that Domino’s has scheduling software, they have uniform requirements, they have policies that they require their franchisees to follow, as far as employment, and therefore, they are effectively the employer, as well. Now, in my mind, in our way our legal system works, if you can get six franchisees, that’s fine, but if Domino’s has a problem nationwide, then suddenly you could have a nationwide class action with Domino’s Corporate being the target. You can help clean up and police a whole industry by going after a case like that. The economics don’t work if you can’t have a sufficiently large class.

From US Supreme Court holdings and what the US Chamber of Commerce has done, they are trying, deliberately, to limit their exposure to employment suits, and thereby avoid their responsibility for cleaning up bad practices. To me, the attorney general in New York was tearing down a wall of privilege that Domino’s and others similarly situated have created to protect themselves to from exposure to a legitimate claim for wage theft by employees. It’s just enforcing the law equally for everyone, but figuring out ways that the system has been manipulated to favor certain people.

Sam Glover: Oh, sure. I’m a small businessman. I am fine with the rules being whatever they are, as long as they apply to everybody. Sure, certain tax outcomes make me happier because I get more money in my pocket at the end of the day, but at the same time, I recognize that those take a toll on our society, which I also want to succeed. I want Minnesota to do better, and if that means me paying more taxes, then okay, but If I look over across the street and realize that in another building, there’s a business that is getting away with something by playing with a different set of rules, that sucks.

Ryan Winkler: Exactly. They are able to do it not because they are smarter about it, but usually it’s because they have more influence in the political system, or they have legal representatives who they pay a lot of money to figure out ways of creating rules that are going to be favorable to them. Yeah, we always talk about taxes, but in a million ways throughout the economy, this kind of fencing out competition happens all the time. As you said, you run a small business, my dad builds log homes for a living. I grew up in a small business family.
I spent most of my legal career working in a business environment, and these are, for the most part, small companies with big ideas of trying to change the market. I consider a fair marketplace to be probusiness. That is what the marketplace is supposed to look like. It is supposed to be a fair place for people to compete with each other. Tearing down walls of privilege is just a metaphor for the idea that people have been very successful in creating space for themselves where they can do what they want and not face that kind of competition.

Sam Glover: Yeah. You fight your way up from being a business, a small business to a big business, to a huge business, and then you start looking for ways to consolidate it by accepting yourself and exempting yourself, and that ain’t fair because the probusiness means pro-all business.

Ryan Winkler: Right.

Sam Glover: The small businesses are the engine of the economy, I think. I feel like I’m quoting somebody by saying that.

Ryan Winkler: Most business, yeah. There are a lot more of them, that’s for sure.

Black Lives Matter and the Broad Role of the Attorney General

Sam Glover: Yep. A different kind of privilege, does the attorney general have a role to play in resolving complaints like those of the Black Lives Matter movement?

Ryan Winkler: Yes. The attorney general has a broad role in trying to make sure that society’s built on a notion of equal justice under the law. You could get into specific cases, specific shootings, it could be about police, it could be about prosecutors and the huge number of charges they can stack up in order to make people want to plea. There’s lots of things that are specific issues, but broadly speaking, the attorney general has a civil rights role and has a criminal justice role. If nothing else, it’s a bully pulpit in a place to convene people and say, “We need to figure out how to do this together.”

The best example of that, in my mind, is, I think, 1965, Attorney General Walter Mondale got a letter from the Florida attorney general asking him to join an amicus brief apposing Clarence Gideon in his effort to get right to council. Mondale, instead of going along with Florida, decided that he would get a bunch of attorneys general like him who are concerned with civil rights, and they instead filed an amicus brief supporting Clarence Gideon. Of course, the case came out in Gideon’s favor establishing a right to council.

Sam Glover: It’s a little important.

Ryan Winkler: A little important. Now, if he had narrowly interpreted his job to represent state agencies, he would’ve said, “Well, it’s going to cost us more money, and therefore, it would not be in the interest of the state to spend more money in taxpayers.

Sam Glover: Or even just a pro-prosecutor, like, “No, everybody guilty goes to jail.”

Ryan Winkler: Right. His view of his role was broader. It was that he needed to be an advocate for justice in Minnesota. In fact, he did so nationally, but at the time, as attorney general, he needed to be an advocate for justice because there is no other office, or no other place in the government, where you have somebody whose job it is to be an advocate for a broader sense of justice under the law. You’re not a prosecutor, you’re not a defense lawyer, you’re not a legislator, you’re not a governor. Your job is to look out for these broad principles.

I think, to the question about Black Lives Matter, absolutely, there is a role for the attorney general to try to figure out what kinds of policies, what kinds of training, what kind of practices we’re engaged in, and how that affects people. In my mind, unfortunately, so much of the debate comes down to an accusation of a racist cop. Any person that you know may be racist, to some degree or not, right? None of us are free of bigotry, in some way, shape or form.

Sam Glover: Right.

Ryan Winkler: You put people in very difficult positions, and if they’re poorly trained or if they’re told to do something where they’re left on their own, bad things are going to happen. Yes, you could have a racist cop who goes out there and seeks people to kill. I think that’s a relatively unusual occurrence.

Sam Glover: That’s also the easier one to address.

Ryan Winkler: Yes.

Sam Glover: A bigger problem is the systemic racism in the system.

Ryan Winkler: What does the city council expect its police officers to do in patrolling traffic stops? What are their expectations? What resources do they have to make sure that the job is being done well? What consequences are there internally short of being criminally charged for higher incidents of pulling certain people over? Things like that.

There’s a ton of work that needs to be done, and I think the attorney general’s role is to step back, try to bring people together, and look at where in the system you could make some changes. Change some incentives in order to pursue a more racially blind justice system.

Sam Glover: I suppose there’s some higher level stuff, too. How has the system been designed so that some of the factors that cops are using to make decisions out on the beat? The staffing decisions, or the decisions about where cops are going to patrol, I think they’re probably, in the same way that we’re learning right now, that some algorithms designed to help judges make sentencing decisions have actual racism built into them because of the way those algorithms are constructed. There’s some weeding out of stuff, too.

White, Middle-Aged Male, Privilege

Sam Glover: One of the things I’m curious about, though, here we are, two white men approaching middle age who are about as privileged as you get. We didn’t ask for that, but we have it. How do you address a problem like policing when you’re sitting on the privileged side of that issue? What’s the best way? How would you even start to break down that wall and have a face-to-face discussion about it where you can actually make something happen?

Ryan Winkler: I think the place that it has to start are relationships with people, and building, over time, a notion of individual trust so that if you’re having a conversation with somebody about a tough issue, they know you’re coming to it in good faith. You may not always get it right, you may not understand initially, but you’re coming to it in good faith and you’re open to learning about it from someone else’s point of view. Nobody has a lock on the truth. There isn’t one person whose view is correct.

Even in, of course, communities of color, and advocates, and Black Lives Matter, there are varying points of view and disagreements and perspectives. I think building relationships with as many people who are effected and who are on the other side of the issue is very important, especially tough issues. We’re talking about life and death. We’re talking about a very basic notion for some people of whether they’re valued in society or not. For others, we’re talking about a very core notion of whether they’re a good person or not.

Sam Glover: Right.

Ryan Winkler: Those are not easy conversations to have. If you’re not doing it from a place of trust, I think it just turns into shouting very quickly. I think that protest is important because it has changed the conversation, and that’s important. It sets the stage for reform and it sets the stage for improving policies and decision-making, but that alone won’t do it.

That sets the stage, and then the next step has to be people being able to have a conversation together and trust each other enough to know that if they disagree and they need to work something out, it’s not because they’re trying to say, “You’re not equal and your life isn’t important. You don’t matter,” and somebody else saying, “Well, the only reason you disagree with me is because you’re a horrible racist person.”

Sam Glover: I supposed anyone who wants to try and mediate a positive result has to convince police who believe that they’re being attacked as a bunch of racists and Black Lives Matter movement people, and lots of people on various shades of other sides, but Black Lives Matter movement, I don’t know if members is the right term, but people who are participating in that who believe that cops are racist and are out to get them, and that they’re in danger, and they’re not valued, and that this is evidence of that. You’re trying to get people with really apposing views to both believe that you are fair-minded and willing to listen. That seems like a really tough challenge.

Relationships, Compromise, and Optimism

Sam Glover: Your answer is relationships, which I want to say to the listeners, that feels like an unsatisfying answer, but I feel like we undervalue that. It really is someone who is willing to build relationships and really do it. That is how we solve problems. That really is.

Ryan Winkler: I’m a politician, so I’m in the relationship business. You can’t accomplish much in a legislative body without relying on personal relationships, even when you disagree. There are plenty of power levers that you can bring to the table, but in the end, you need to have some ability to have a handshake and say, “Okay, we can do this. I trust that you’re going to actually follow through on what you said. I’m going to do what I said.”

It doesn’t mean agreement, it just means, I think, a presumption of good faith on the other person’s part. I don’t know how else to do it, but I also know that of all the people who are protesting, of all the police officers out there, all of the union representatives, and city council members, and mayors, it seems like a lot of people, but in the end, it’s a doable number of people to start relationships and have conversations.

Sam Glover: It just struck me that, as lawyers, we often approach settlement with our clients, for example, by saying that the best settlement you can get is one where everybody is unhappy with the result because it means that the plaintiff got as much money as they could squeeze out of the defendant, and the defendant gave as little as they could persuade the plaintiff to accept. It seems like that’s not a very politically expedient outcome when it comes to something as charged as policing. How do you get the best result for everybody and convince them that it was a good one?

Ryan Winkler: In politics, the standard would be different.

Sam Glover: I’m sure.

Ryan Winkler: In politics, the standard would be that everyone can declare victory. Everyone has a sense of having come out with something better than they otherwise would have, and to be able to claim that knowing however they feel about that inside, it’s being able to go to a press conference and say that we’ve come together and we’re all winning, and we’re all happy. Now, I think that this is going to be a longterm challenge when we’re talking about civil rights. It’s been centuries in the making. One step forward, two steps back sometimes.

This is not something that ever goes away. The question is, can you create an environment in which people can solve problems before they become so manifestly unjust that the only recourse people have is to protest in the streets?

Sam Glover: Maybe we’re getting far afield here, but there’s an author I follow on Twitter called Ramez Naam, he writes some really cool sci-fi stuff, but that’s not why I follow him. The reason I follow him is because he is a dedicated optimist. At the worst times, he always reminds you that the world is freer and fairer. There’s less poverty, there is more renewable energy.

Ryan Winkler: Disease is on the decline.

Sam Glover: Yeah. Essentially, everything is better, and everything continues to get better. In light of these seemingly intractable problems, in light of politicians who we hate getting elected, whether that was eight years ago for you, or two months ago for you, everything is getting better. In some ways, the problems that we’re trying to deal with now are difficult and complicated, and we have to tackle them, but in some ways, they feel worse because we’re so close to getting to where we hoped we would be. In many cases, we’ve actually passed the bar where we hoped we would be, and now we’re dealing with new problems that we weren’t even aware of before.

Ryan Winkler: Right.

Sam Glover: I’m not sure exactly what that has to do with charging you with the job of AG, but maybe it’s from my own, whatever context you put me in, I think it’s worth reflecting on that. Maybe it helps when we’re thinking through these really hard issues to back up every once in a while, look at the bigger context and say, “You know what? Overall, stuff’s improving. Things are getting better.”

Ryan Winkler: That’s true, but if people don’t feel that way, it doesn’t matter.

Sam Glover: Yeah, that’s true.

Ryan Winkler: In our political decision-making, our trust in institutions is extremely low.

Sam Glover: I suppose it’s easy to point at me and say, “Well, you’re privileged white guy for whom it’s easy to have that positive view.”

Ryan Winkler: It’s absurd to say, but the poor are doing better than the poor used to do in their material wellbeing. Extreme poverty around the world is on the decline. There are measures, objective measures, that indicate things are getting better for more people, but I think we’re also in a time of great social disruption. The last time we had such an era was when rapid industrialization basically destroyed the farm and the small town as the basic unit of American life and built massive cities. Today, we’re seeing, in some ways, those things going global, and we’re also seeing the rise of people who, historically, were lower on the social hierarchy than they are today, and yet still not up to full equality, but have been on the rise, and so people who once were on the top, who thought that if you’re a white male and you got a high school education, you could feed a family of four or five, and life was pretty good to be an American, for that group of people, their relative status in society has declined for various reasons, and we’re having a big national debate about why that is.

There are those who will easily point to the old escape goats of race, and outsider status, and sexual orientation, and point to those outsiders as the threat to the traditional hierarchy. In fact, the traditional hierarchy, defined as through gender and racial terms, is being upset, and it’s being upset by people who are claiming their rightful place. It just leads to a lot of social disruption, distrust, uncertainty about what the future looks like, and when you’re not sure where you stand, it’s hard to say, “Well, but on the other hand, I’m getting 40% better healthcare than my parents did 40 years ago.” You don’t experience that. That’s not emotion.

Why It Doesn’t Matter That Everyone Is Doing Better

Sam Glover: As you say, it kind of doesn’t matter.

Ryan Winkler: Right.

Sam Glover: When I say everything is getting better, and someone from a greater Minnesota town who’s not feeling that way, I can point, “no, everything is better for you,” and it doesn’t matter because they’re subjective personal lived experience is that things are still pretty shitty.

Ryan Winkler: Right. Exactly.

Sam Glover: That’s true. They’re not wrong about that. It strikes me that one of your challenges, should you become AG, and throughout this campaign is going to be, how do you persuade those in greater Minnesota who are particularly feeling marginalized that you’re going to be their representative, too? It seems to me that if the last election told us nothing else, it’s that they’re not feeling that way. They’re not feeling like the politicians, and particularly probably the democratic party, is on their side, and so how do you persuade them?

Ryan Winkler: I would say that the answer to that is also relationships. I think I have one advantage, which is that I was born and raised in a white working class family in a rural area. That’s still where my family is, and extended family. I’ve seen what happens in communities and in families when things don’t go well.

Sam Glover: You’re not descending from your ivory skyscraper to go out and mix with the rabble in greater Minnesota?

Ryan Winkler: I spent some time in ivory skyscrapers, too. I have a bit of a foot in both places, but people have seen that when their kids or their family members get an education, and they make the right decisions in life, and they’re well prepared to succeed, their life goes pretty well, but they’ve also seen a sibling who makes a different decision and is suddenly addicted to something, or has a gamboling problem, or is an alcoholic, and there’s abuse. There is just a declining welfare in their lives because of that. I think people feel like the consequences for making small errors in judgment are much greater than they used to be, and that people are too busy putting a nice gloss on the way the world is going. They don’t see that there’s been a big divide, and I think it makes them nervous.

Even if you’re still doing well, you still see the sinkhole coming your direction. The question is whether you can run fast enough to get away from it. I think people just have a great sense that if you work hard and do the right things, and you’re a decent person, the future’s going to be better. I think people don’t feel that confidence anymore.

Sam Glover: That is the American dream right there.

Ryan Winkler: That is the American dream.

Sam Glover: If you work your butt off, you should be okay.

Ryan Winkler: For people who are racial minorities, women or others who never had equal status, they’re starting to make progress at a time when other people are descending. It creates a great amount of distrust, and I think a lot of people just talking past each other and yelling at each other, and not seeing that the common link that they have together is that society and our economy are not serving the average person very well anymore, despite the fact that the average person is more productive or harder working than ever, and that there is a systemic privilege that exists throughout our economy and our society that is holding people back. If you could go after that and solve that problem, that everybody could rise together.

Student Loan Debt and the Higher Education Monopoly

Sam Glover: You mentioned a minute ago education, which is a marker. That is what people have reached for. It’s gotten a lot more expensive over the last decades, really. I feel like there is a tuition bubble that has to burst, but it hasn’t yet. When I meet with my financial advisor and he tells us how much we have to save so that our kids can go to college, part of me just is incredulous, but part of me says that can’t continue.

Ryan Winkler: Just tell yourself that having student loan debt will build their character.

Sam Glover: Yeah. I’m not sure that it’s built mine. Between my wife and I, we have plenty. Student loan debt, I feel like it is a problem. Credit card debt made this huge bankruptcy bubble years ago. That bubble burst, and I think part of the reason it burst was because people could only bear so much debt before they actually started declaring bankruptcy. There is no similar bubble that can burst for student loan debt because you can’t really discharge it in bankruptcy. What does that problem look like?

Ryan Winkler: You can’t discharge it in bankruptcy and you can’t get anywhere in life without it.

Sam Glover: Yeah. Then you can’t get anywhere because you can’t get rid of it.

Ryan Winkler: I think, in some ways, higher education acts like a monopoly. You are selling something that everyone feels they need to have, and will do almost anything in order to get it because, otherwise, their economic futures are much diminished. Even people who don’t get a college degree need some higher education, or they often start and don’t finish. Everyone has the perception that a college education is the path to the middle class and there’s no other way around it.

If you’re selling something, a degree, that everyone needs to have, and there’s easy credit in order to buy it, there is very little incentive to bring your cost down and compete with others. I don’t know that they collude in pricing, but I know that they all know what the other charges.

Sam Glover: It’s not a fair market. In law school, there are, basically, lenders shoveling money at you, and you can take out as many loans as you want, basically. You can go ahead and criticize students, law students, other people for not making smart financial decisions, but I don’t think I was qualified to make smart financial decisions until I was well into my 30’s.

Ryan Winkler: It’s exactly right. I think of things like it’s illegal to sell a 30-year annuity to a 90-year-old, right?

Sam Glover: Right.

Ryan Winkler: It’s not the suitable product.

Sam Glover: And a nine-year-old.

Ryan Winkler: We are asking people who are 19, 20-years-old to make longterm financial decisions about their education and investment in what kind of a return it’s going to bring, and they get almost no guidance about these kinds of things in colleges. They get almost none in high school, and we just think, “Well, go out and do your best and figure it out.” This is what kids want to study, and so, as a college, I’ll provide those classes.

Sam Glover: Yeah. We assume that it’s valuable investment.

Ryan Winkler: I would say a liberal arts education is inherently valuable for any person, but how much? There are a lot of good things in life, and how much is it worth going into debt in order to get it? What assumptions are you being led to think about, as far as careers afterwards? I think that we’re asking them to make high-stakes decisions at a time when science tells us they are not fully formed in their decision-making ability, and the stakes are high.

The consequences can last a lifetime, and so I’m concerned about that. It goes beyond just the consumer fraud and the ease of the debt, it’s also the guidance that they get.

Sam Glover: Yeah, because again, those are easy problems. Abusive debt collectors, we’ve got good laws on that. We can deal with it.

Ryan Winkler: Right. It’s the system. One of the things that I’m interested in, and I’m not going to make any claims right now, but one of the roles of the attorney general is to oversee nonprofit corporations. They have to register and provide data about how their operations work. In the past, we’ve seen attorneys general in Minnesota go after nonprofit hospitals and health providers because they’re holding on to too much money, and charging too high rates, and paying administrators too much. Well, that doesn’t sound so different from our nonprofit colleges and universities in Minnesota, either. I think there’s a role to be played in oversight as regarding how much tuition they’re charging, what the social value is of what they’re doing.

Sam Glover: At least in looking at it, right?

Ryan Winkler: Correct.

Sam Glover: You’re not, necessarily, saying, “I’m going to sue Macalester College for charging too high tuition.”

Ryan Winkler: Yeah.

Sam Glover: It’s worth looking at it and making sure the book’s balanced.

Ryan Winkler: Just ask the questions. What social benefit do you get by having your tuition structure tiered this way? They’re not in an easy position either, right? They’re all competing with each other for US news rankings. That means they want the most talented students who are going to stay and graduate the fastest, and have the highest paying jobs afterwards, and so they’re in an arm’s race to compete with those students, which just jacks up the cost even further.

Sam Glover: I suppose we are in a time of disruption when all kinds of businesses and business models are being changed forever. Part of that, too, is what are they doing to adapt? What are they doing, if there is an important thing to adapt? I’m not in favor of change for change of sake, but we’re seeing new efficiencies emerge from all kinds of markets, and how is that, maybe, happening in education, or how could it?

Ryan Winkler: Right. I don’t think it is.

Fighting Unconstitutional Laws

Sam Glover: Yeah. I’m in publishing, which is definitely being roiled by disruption. No, that’s an interesting thing. I’m going to totally change gears here. One of the other things that you said, and this was almost immediately in the wake of the election, and the reality is that many of the things that our president-elect promised were unconstitutional. You said that you would stand guard and fight any unconstitutional laws in Minnesota.

I’m curious, now that we’ve had some weeks, a couple of months in the wake of that, I still don’t think we have any idea what the Trump administration is going to look like, or what a republican-led congress is going to actually do, so I realize this is all conjecture, but what do you think that might look like? What does it look like? I think we can look back at history for this. When the federal government passes an unconstitutional law, what does it look like when a state rebels against that?

Ryan Winkler: I think an important part of how states can react to that is by working together and engaging in multi-state litigation, which there’s a long history of. If you combine states, like New York, California, Massachusetts, Illinois, Washington state, Minnesota, you have states that have pretty outsized economic power in the nation and in the world. That’s one of the ways, for example, that they were able to change the practices of the tobacco industry, was by working together across state lines, and taking on an industry jointly, and changed the way they did business. They haven’t quit trying to fight their way back, but they’ve been significantly hobbled, and then there’s been a lot of money going into public health as a result of it.

I think part of the way it looks is by banding together. The second is there are, of course, challenges all through the Obama administration by state attorneys general going after Obamacare, going after the Clean Power Plan, and I’m sure the list is endless. I think the quote from Attorney General Abbott in Texas is that he saw his job as wake up in the morning, sue the Obama administration, go home at night. Now, I think that’s just obstructionism and animosity, but the point is where there are things that are our core values that the state and the people in the state care about, the attorney general should be there and should be looking for as many allies in other states to team up with to fight them off.

Sam Glover: I supposed it’s worth mentioning that many of the great constitutional law decisions that we study in law school came from Minnesota. I don’t know if that’s just coincidence or because we’re just more awesome about fighting unconstitutional things, but we have generated an outsized influence on Supreme Court jurisprudence’s, it seems like.

Ryan Winkler: That is true. We may have an opportunity to do that again, but that probably will depend on who the court is. Who the court and who the AG is. Were also seeing conservative groups launching lawsuits all over the country, in areas that they care about, hoping that in two to three years time, they’re going to have favorable judges in the US Supreme Court, and other places, who are going to rule their way.

Sam Glover: There are a record number of vacancies in the judiciary across the country.

Ryan Winkler: Correct. For example, there is a couple in St. Cloud who, I don’t understand how they have a claim, they want to go into the videography business at weddings. They’re not in it, but they want to, and so they’re suing to overturn on a facial basis Minnesota’s Human Rights Act because it says that if you are open to the public and offering your services, you can’t deny them based on the fact that the couple is same sex. They are suing the state of Minnesota. The attorney general will defend state statute. They are being funded by a national conservative organization, and as I said, they’re not even in the business yet, but they say they want to be, so we’re going to see not just state attorneys general trying to counteract unconstitutional laws, or laws that violates people’s civil liberties coming from the Trump administration, we’re also going to be in the fight as private organizations fund lawsuits to try to overturn some of the core principles and the core legal protections that Americans have today.

I would expect in that St. Cloud case, I don’t know how far it goes, and I’m sure that they have at least one launched in every state that has this kind of law in the books, and so we will have to be teaming up and figuring out the best strategy for fighting off those kinds of private actions against civil rights and other state protections.

Representing Minnesota

Sam Glover: When you think about who do you want in that office, who do you want overseeing the defense of the Minnesota, the good Minnesota laws when those things happen? You want somebody who will use their discretion to decide this is something we need to fight hard on and to make sure that it stays on the books when it’s a good law. When it’s not a good law, Gideon was a great example, sometimes you need to say, “You know what? We think that needs to change, and here’s how we can use this office to make it change.”

Ryan Winkler: Correct, and be willing to go to the voters after a term of office and say, “This is what I’ve done, this is what I believe is in the best interest of justice, and for the best interest of the people, of the state. Judge me accordingly, but I’m not going to do something different just because I think that it’s going to be an argument, or that somehow, some other organization is not going to like it.”

Sam Glover: I think that’s, maybe, a good note for us to close on. Ryan, thanks so much for being with us today. I know it’s very early in the campaign, and we’ll be hearing much more from you over the next two years, at some point.

Ryan Winkler: That is the goal.

Sam Glover: Good luck.

Ryan Winkler: All right. Thanks, Sam.


  1. Ryan does not intend to challenge the current Minnesota Attorney General, Lori Swanson, but she is widely expected to run for governor in 2018.