Many questioned the political wisdom of St. Paul City Council Member Bob Sylvester's decision to publicize his transition from man to woman in the early 1980s.

He became Susan Kimberly, and now she is retiring -- for the third time -- after decades of service to the city she loves, St. Paul.

An adviser to mayors, a dealmaker, a policy wonk in every sense, Kimberly, 68, has earned respect from people inside and outside City Hall while keeping a strong sense of self and interest in city issues. That's in spite of two major transformations -- changing genders and switching political parties in a mostly one-party town.

"I lost more friends becoming a Republican than I did becoming a woman," she said.

In a week Kimberly will walk out the doors of the St. Paul Area Chamber of Commerce, where she has been an executive for the past few years.

Susan Kratz, chairwoman of the chamber board, praised Kimberly's managerial skills and passion for her work.

"She has a wonderful ability to be firm and forceful on issues that she feels are important," Kratz said.

"She continues to maintain strong relationships even with people she disagrees with."

There have been plenty of disagreements over the years, from neighborhood issues to political ones. Still, Kimberly has stuck around.

Gender change

Kimberly is the "former-just-about-everything" in St. Paul government.

Sylvester served on the City Council from 1974-78, including two years as president. He was head of the Housing and Redevelopment Authority. Later he left politics to become an investment banker.

Sylvester revealed his desire to become a woman in 1983 and had surgery in 1984 to become Kimberly. A few years later, she was back in City Hall, working for Mayor George Latimer. Then she led a coalition of neighborhood development corporations.

She had two unsuccessful bids for political office in the early 1990s, running for City Council and Ramsey County Board.

Kimberly said it was good she didn't get elected because Norm Coleman, then mayor, wouldn't have picked her as his deputy mayor in 1998. It's the highest non-elected position in the city and a post she loved. She also worked for him when he was elected to the U.S. Senate.

After that, she led the city's Planning and Economic Development department under Mayor Randy Kelly.

She's proud of the work she did with Coleman trying to lure the Twins from Minneapolis, pursuing a major housing initiative under Kelly's tenure and helping to form a downtown district energy system.

Kimberly said she wished she hadn't sponsored the resolution setting up the city's District Council system, which was intended to give neighborhoods a bigger voice inside City Hall. What's resulted instead, she said, is too much diffused authority and not enough focus on the city as a whole.

Except for a stint in the 1960s in India for the Peace Corps and her first five years growing up in southern Minnesota, Kimberly has lived within a two-mile area of Selby Avenue and Dale Street.

"A lot of people would say that what's unique about my career is that as a transsexual who went through a very public gender transition, the amazing thing is that I stayed in place," she said. "I will tell you that it is hard for me to believe what a welcoming and tolerant community St. Paul has been for me. I love this place. Even if it drives me crazy sometimes, it's just a fascinating place to be."

And a party change

Once a young Republican, Sylvester knew he needed to be a DFLer to win office in St. Paul. Kimberly, however, grew to eschew big government and made her switch back to Republican roots.

She believes in free trade, limited government and fiscal restraint. She has her doubts that the GOP as a whole believes in those things, and a portion of the party is "too committed to disliking people like me and having problems with people from different countries."

Although her gender and political philosophy have changed, Kimberly's analytical qualities, speaking style and sense of humor haven't, said Latimer, who worked with both Sylvester and Kimberly. "Susan is one of those, I think, rare people who is a strong conceptualizer and strategist and a very good writer," he said. "But also she mastered the numbers very early."

Coleman echoed that assessment. "She knows government, she knows finance and she knows politics," he said. "She has good judgment, and if you have good judgment, people trust you."

What comes through clearly is Kimberly's the trust in herself and the choices she has made. She came to terms with her life as Sylvester a long time ago; it's "part of my résumé."

She still hangs out with the woman Sylvester was married to for 10 years.

Kimberly has come to accept the world as it is, that things aren't supposed to be different. Also, she believes people do the best they can under their circumstances. "There's no point in being angry and resentful. We judge ourselves and everybody else all the time and, really, what's the point?"

As she attempts retirement again, Kimberly has plans to try to finish her autobiography and improve her golf swing. She might try snowshoeing.

Like so many other retirees, she also plans to travel. The next big trip will probably be Paris. Of course, in keeping with her wonkish ways, Kimberly's sightseeing priority is infrastructure. "I hear they have a really neat subway system in Paris, and it's laid out in a way that serves urban vitality," she said. "I also will go to the Louvre."

Chris Havens • 612-673-4148