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And though he claims he has not made a decision, the widespread belief in political circles is that "the Dean," as his fellow commissioners are fond of calling him, will soon announce that his career as an elected official, which has spanned nearly 30 years, will end when his term expires this fall.
With Winn promising to announce his plans at the February 1 commission meeting, the two leading candidates to replace him have been quietly jockeying for position in what promises to be the most contentious race among the six county commission seats up for grabs this year. Former Democratic state Senator Gwen Margolis opened a campaign account earlier this month with a $15,000 deposit from her personal funds. At the same time, former Democratic state Representative Michael Friedman has hired political consultant Phil Hamersmith as his campaign advisor.
Margolis and Friedman are circumspect about their intentions. Neither of them has officially declared themselves a candidate, nor would they discuss in any detail why they want to be a Dade County commissioner. "I'm uncomfortable talking about this," says Friedman, a Miami Beach city commissioner for three years before serving as a state representative from 1980 to 1992. "Sherman Winn is the county commissioner until he announces otherwise. Out of respect for his contribution, I think it's too presumptuous to talk about this now." Margolis, who lost her 1992 bid for Congress to incumbent Republican E. Clay Shaw, echoes those sentiments. "I'm waiting for Sherman to make his decision," she demurs.
Both 59-year-old Margolis and 45-year-old Friedman say they will not run if Winn decides to seek re-election. But that may be the only thing these potential rivals agree upon.
"If Sherman Winn doesn't run, this should be a real donnybrook," predicts consultant Hamersmith, who claims a personal interest in the outcome. "I don't like Gwen Margolis. I don't like her as a person. I think Gwen Margolis is an overrated candidate. She comes with a tremendous amount of baggage. She's not a woman of honor and she lacks charisma." The ever-outspoken Hamersmith then adds, "I think I'm going to enjoy this campaign."
The enjoyment, presumably, would only be enhanced by the prospect of Hamersmith facing off against his former partner, Rick Sisser. While stressing that everything depends upon Winn's decision, Sisser says he will work for Margolis as an unpaid senior advisor to her campaign. And in response to Hamersmith's comments, he laughs and says, "Philip has always had his opinions, and it's because of his opinions that we are no longer partners. Phil likes donnybrooks. I prefer easier races." With Margolis as a candidate, Sisser asserts, this contest would in fact be easy: "If Sherman doesn't run, I believe with all my heart and all my soul that she will be the next commissioner from District 4."
Margolis, who served in the legislature for eighteen years, initially as a representative and ending as president of the Senate, is considered the early frontrunner. A successful realtor and developer, she spent several hundred thousand dollars of her own money on her failed congressional campaign and she says if she runs for county commissioner, she is once again prepared to spend as much as necessary to run an effective campaign.
In addition to the advantage of substantial finances, Margolis enjoys a coincidence of geography: The boundaries of Winn's recently created commission district are nearly identical to Margolis's former state Senate district in Northeast Dade. She would be campaigning before voters who have elected her in the past.
Margolis also can boast that while she did lose to Clay Shaw in the 1992 congressional race, she won the Dade County portion of Shaw's district with 63 percent of the vote.
The Margolis camp may see the glass as 63 percent full, but Friedman's supporters note that it was also 37 percent empty, and in that they see an opening. "Clay Shaw is not a familiar name in Dade County," Hamersmith argues. "Gwen Margolis should have had 83 percent of the vote in Dade for that race. That was part of her problem A she didn't receive enough support in her own county to offset Shaw's strength in Broward. She's vulnerable."
If Winn does decline to seek re-election, it may only mean he's changing offices. The Brooklyn native, who turns 71 next month, began his public-service career as the mayor of North Miami in 1965, followed in 1970 by a two-year stint in the state House of Representatives and then ten years in the state Senate. In 1982 he was elected to the Dade County Commission, where he is now the senior member. Should he step down from the dais, Winn reportedly will angle for the job of director of the Sister Cities Program of Dade County, which promotes the county's cultural and economic ties to twelve cities around the world.