Anthony Weiner's bizarre modeling habit did not start on Twitter. New pictures have surfaced from 1982, when Weiner was in college at the State University of New York in Pittsburgh. The photos show a then 18-year-old Weiner posing in swimming briefs and in women's underwear. According to a friend, the photos were taken as part of a secret Santa tradition, which required participants to complete challenges in order to obtain their presents. Though the friend recalled, "It was never quite clear whether one of Anthony's challenges was to become a cross-dresser or if it was just some bizarre stunt he decided to do on his own." Apparently, Weiner "was an odd guy who went out of his way to do things purely for shock value." Another friend described an instance in which he ran for student senate and decided to use the campaign slogan "Vote for Weiner. He'll be frank." The campaign was unsuccessful.
Just before the local primary, photographs of East Cleveland Mayor Eric Brewer, posing in lingerie, surfaced on a television station last week. In one image, the mayor struck a sultry pose in a wig while wearing prominent lipstick. Brewer blamed his opponent and the Police Department for the images’ distribution. The mayor lost the election and seems to be suffering for friends. "It's him, alive and well," a former East Cleveland mayor told reporters. "Because the guy got demon eyes. You can't put them on a woman."
The first time Stu Rasmussen was elected mayor of Silverton, in 1988, he campaigned in pants, but he was voted out of office four years later. The next time he returned to the campaign trail, it was in heels and a skirt. Foreshadowing the fate of his fellow mayor, Eric Brewer, Rasmussen said that his decision to go public with his cross-dressing preserved his candidacy. “I blackmail-proofed myself,” Rasmussen said in a November 2008 interview. The first openly transgendered mayor in the country. Rasmussen was recently filmed for a reality television show. “It’s almost my responsibility to the rest of the transgender community to help others that we are not freaks and weirdos,” he has said. And while the residents of Silverton are open-minded, they are not accepting of everything. This summer a formal complaint was filed against Mayor Rasmussen for showing a little too much skin.
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Perhaps only Rudy Giuliani could believe that he could win over the country’s conservatives despite having a closetful of peculiarities. America’s Mayor strutted his stuff in a pink gown and blond wig at a 1997 roast. He reprised the drag act for the audience of Saturday Night Live a year later. "People think of him as a leader and a tough guy, and he has this image as somebody who tamed the city of New York and made the trains run on time, and seeing him dressed up like a girl would run contrary to all of those things," one political audience member said at the start of the 2008 campaign. As Rudy flirts with another run at higher office, will the skirt reemerge as well?
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Once Kwame Kilpatrick’s problems seemed relatively small. When The Hill published a photo last year of the young Kilpatrick, then an eighth-grader, wearing a red dress in a school production of “Little Annie,” Kilpatrick’s camp released a forceful, if absurd, denial. Even though Kilpatrick’s name appeared in the playbill, his spokesman maintained, “The mayor says he did not participate.” At the same time, Kilpatrick was denying sending scandalous text messages to an aide. One revelation ended in embarrassment—the other prison time.
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Although eventually bounced from office in 2006, Vladimir Luxuria made news by campaigning against conservatives as a transgendered candidate for Italy’s Communist Refoundation Party. Luxuria, who considers herself neither male nor female, said in 2006 that the country should protect "all the gays who try to get into Italy from countries where homosexuality is punishable by death.”
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Further proof that while crossdressing may be a brave statement, it is often a political killer, Sam Walls lost his campaign for a seat in the Texas State House to a fellow Republican in 2004. Walls said crossdressing was “a small part of my personal past” during the campaign. “He's always been a gentleman, a class act,” a friend told reporters.
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Believed to be the first openly gay candidate ever to run for public office in the United States, Jose Sarria was a nightclub singer in San Francisco. "There is nothing wrong with being gay," Sarria would sing at The Black Cat bar on Montgomery Street. 1n 1961, Sarria took his political activism from the stage to the stump, filing as a candidate for a seat as a San Francisco supervisor. Sixteen years later, Sarria backed Harvey Milk in his campaign for city supervisor.
It turns out Rudy Giuliani was not the first New York politician who took refuge in the soft folds of a lady’s garment. While Puritan mores still ruled the land, in fact, while Puritans were still alive and kicking, Edward Hyde, governor of New York and New Jersey from 1701 to 1708, dressed as woman. He reportedly told the 1702 New York Assembly that since he represented the queen, he would dress like her. Apocryphal or not, a portrait of a cross-dressing Hyde hangs in the halls of New York Historical Society.
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