If you've followed issues in St. Paul, from the city's garbage wars to historic preservation debates, you're likely familiar with Tom Goldstein. He's the guy who, in his words, has "demonstrated experience challenging the status quo."

A former member of the St. Paul School Board who has run for City Council and mayor, Goldstein is a frequent critic of City Hall. A Democrat in a DFL-run town, he nonetheless often takes contrary positions to the city's favored pitch. Whether criticizing using property taxes to develop the former Ford site or opposing a teardown of the Hamline Midway library, Goldstein says he fights to hold city leaders accountable.

Eye On St. Paul recently sat down with the Maryland transplant to talk about what fuels his clashes with the powers that be. This interview was edited for length.

Q: When did you graduate from Carleton [College]?

A: I was in the class of '79. But I graduated a year later. I took some time off and I ended up moving to Minneapolis for a year.

Q: What did you do?

A: I wanted to get some time off. Carleton really wasn't a great school for me. I felt really isolated. And it was very intense. I'm a pretty social person and I adapted eventually, but there were a lot of really intense, smart, driven people who weren't necessarily very socially adept. I took a year and ended up getting a job at Haskell's liquor store. That was the first time I was ever in a liquor store. I'm not much of a drinker.

Q: What was your major?

A: Psychology. I was a pre-med in college, which was a huge mistake. I never really asked myself what I wanted to do. When I finally asked that question, I said, "No." You know, I'd always sort of assumed I'd go to law school. I ended up going to law school.

Q: Where did you go to law school?

A: William Mitchell.

Q: Did you go right after college?

A: No. I went for about three years, then for whatever crazy reason, I ended up opening a sports store that I had for 14 years. I started on Grand [Avenue], then moved over to Marshall Avenue. I don't know why. I'm still trying to figure what that was about. I just wanted something different from law school. I ended up going back [to law school] in the evenings. As a result, I didn't end up taking the bar exam for 20 years.

Q: Why not?

A: I got busy. Got married. Had a kid. Got divorced. I was working at the Legislature ... [later,] I managed to [pass the bar].

Q: Do you think you're still looking for direction?

A: I think I'm one of those people that unfortunately — because I challenge the status quo — I don't really have a place. I think my passion is really people. I mean, people may not perceive me that way because I'm critical of how the city operates. But that's really what's beneath it.

Running for office was never about my ego, which I think made politics difficult because [it attracts] a lot of egotistic people and a lot of people who are just looking for their next move. I was just looking to actually improve things.

I ran for School Board after getting involved in some issues at my son's elementary school.

Running for mayor, I was pretty clear about what the odds were. I just felt like if the candidates were really progressive people who were going to actually change things, I wouldn't have run.

Q: St. Paul gets called a one-party town. But you're proof that there are still differences. What is the number one reason that St. Paul is succeeding or not succeeding?

A: I would say the lack of accountability. People like to say that accountability is at the ballot box. And I have had people try to argue that if there's low turnout, and there's an incumbent, then they think they're doing a good job, which I think is baloney. If you want to evaluate St. Paul, where I think St. Paul is in really serious trouble — look at the streets. I would be embarrassed to have anybody come to St. Paul.

The other way that it's apparent is there are no jobs of significance being created in St. Paul. We have these huge plans: sick and safe time, to raise wages, to provide [college] savings accounts. We have these goals we want to achieve as policies, and yet Democratic leadership in this city seems to have no clue.

For all their talk, St. Paul can be an extremely parochial place. It's this big machine that runs on, and there's no real scrutiny. It seems to me that people who are in key positions are just cronies to the mayor.

People who live in St. Paul don't want to hear that their city is a problem. It's psychological. People grew up here, their kids are here, their grandparents are here, they don't want to hear their city has problems.

Q: What has to happen for that to change?

A: Honestly, that's why I'm really concerned about St. Paul. I think it would take a major crisis.