In a 2008 WTTW interview, Flint had this to say about the opening of The Baton club: “So I thought, ‘We'll start a drag show, like the Chesterfield.' So I got a kid named Lady Baronessa, Samantha George, Jody Lee, and myself, and we put down about 16 beer cases, put a little curtain around it, and a little spotlight. And we started the show. The place got packed on Friday night.”

Flint's character, Felicia, was more comic than serious drag ( he retired her in 1985 ) . As to the origin of the name The Baton: It was a skill and a sure way to draw a crowd. “I was a drum major in high school, and I would start twirling back and forth across the street on roller skates, and then I would stand in the middle and twirl my baton.” Almost 40 years later, The Baton Show Lounge still features top female impersonators playing to packed houses. Flint is also the founder and owner of the Miss Gay Continental Pageant, a national female impersonator contest that annually draws a crowd of nearly 1,500 and is franchised in numerous cities across the United States and Canada.

Flint's experience in the gay bar scene of the 1960s is fascinating. At that time, several Chicago-area gay bars had rear entrances with no markings except for the address. Touching or dancing with a member of the same sex could prompt a raid, with everyone loaded into paddy wagons and the names of those arrested printed in the newspaper. This common police practice randomly ruined hundreds, and possibly thousands, of gay and lesbian lives.

During this time and into the early 1970s, raids and incidents of police harassment were routine. If a bar wanted to remain open, payoffs had to be given to both the police and the mafia. In 1971, he says, gay bars banded together against continued extortion from officers. As a result of the ensuing investigation, dozens of offending officers were jailed. Flint and many others thought that era was finally over. When it seemed to begin again in 1980, Flint helped organize a demonstration in which thousands of protesters marched to Daley Center Plaza and demanded an end to police harassment. In his WTTW interview, Flint says that he told then-Mayor Jane Byrne, “I don't think you or anyone else knows that we can mobilize. And I don't think you think we're really going to go through with this, but we are not gonna tolerate police harassment anymore.” After that, the police harassment stopped, for the most part. It was several years earlier, in 1971, that Flint says he decided he was no longer going to pay off anyone, and that included the Mob. However, that was not the case with other gay bars. In the late 1970s, owners of Carol's Pub, the New Flight, and the Glory Hole worked with federal agents on an undercover sting operation against organized crime. When the case over extorting funds from gay bars during 1978—79 finally came before a grand jury in 1984, Flint says he testified about his refusal to make protection payments to the Mob and that evidence showed that, in fact, he had refused to make the $500 monthly payments. He recalls that one of the defendants remarked, “He's got balls, that Jimmy Flint,” about his refusal to make payments. The trial resulted in one of the five indicted defendants being found guilty.

Flint was also one of the founding members of the Windy City Athletic Association, giving gays and lesbians the opportunity to participate openly in amateur sports leagues. In 1979 Flint helped organize a 12-inch softball league. It was wildly successful from the start. The following year, bowling was added to the roster, and then basketball. Since that time, Flint has served as the Windy City Athletic Association's commissioner more than once, and has sponsored dozens of teams.

Flint's political activism includes leadership of the 1980s—era Prairie State Democratic Club and running a very close race for election to the Cook County Board in 1987—when the elections were citywide, not by district. In 1977, Flint was a key part of the march around Medinah Temple where homophobe ( “God made Adam and Eve, not Adam and Steve” ) Anita Bryant was appearing.

In the late 1970s and into the early 1980s, Flint was also president of the Chicago Knights MC, a leather and Levi's club that raised money for Toys for Tots. In the mid-1980s, he helped organize community forums that eventually led to the establishment of Chicago House, a hospice residence for people with AIDS. He was vice president of the 46th Ward Democratic Organization from 1984 to 1986. He is a member of the International Gay and Lesbian Travel Association and an active member of Dignity/Chicago. He was inducted into the Chicago Gay and Lesbian Hall of Fame in 1991, and in 2000 Flint was the first Chicagoan to be inducted into the North American Amateur Gay Athletic Alliance Hall of Fame for contributions to gay softball.

In addition to The Baton, he has also owned such businesses as Annex 2, Annex 3, Redoubt, Redoubt Atlanta, and River North Travel. He is a member of the Rainbow Coalition, the Independent Voters of Illinois —Independent Precinct Organization ( IVI-IPO ) , the Lake View Citizens' Council, and Operation PUSH.

Flint's activism and visibility have resulted in his being arrested 16 times. Clearly, that defendant was right to comment that Jimmy Flint has balls. And all 16 times, he has been found not guilty.

Copyright 2008 by Owen Keehnen

From Out and Proud in Chicago: An Overview of the City's Gay Community, edited by Tracy Baim, Surrey Books, 2008.