Long before Stevie Nicks first sang "Leather and Lace" Jim Flint was running leather bar Redoubt and drag club Baton in Chicago, IL.
The gay club owner is the subject of the new biography The Boy From Peoria by Tracy Baim and Owen Keehnen. Like their earlier book Leatherman in which Baim and Keehnen delved into the life of barkeep and bathhouse operator Chuck Renslow, the authors once again tell a page-turning story of a gay businessman in the Windy City against a backdrop of the Mafia underworld.
The Boy From Peoria dramatically underscores with exhaustive research how the gay experience for decades was defined by wise guys, and in the fight for liberation the community had to eliminate the Mafia from its bars. Flint began his nightlife career as a bartender during the 1960s in suspected mobbed-up joints, later opened his own venues during the 1970s under the mob's extortionate thumb, and then testified for the feds at a 1984 mob trial. In the end Jim Flint came out on top.
The first gay clubs at which Flint worked in the mid-1960s were drag revue joints The Chesterfield and The Annex which were owned by Nick Dallesandro, and Baim and Keehnen write:
The Chesterfield and the Annex were both managed by Nick's nephews. Skip Dallesandro ran the Annex, and Bobby Dallesandro ran The Chesterfield. It was widely suspected at the time they were on the fringe of the Mafia, but nothing was certain. "I know one time they said the payments weren't in, and they [the Outfit boys] came behind the [Chesterfield] bar at 2:30 in the morning and cleaned all of our registers out and left us a dime, a nickel and a quarter in each register to work with," Flint said.
Jim Henritze, a manager of The Chesterfield, recounts that in 1962 Rush Street crew boss Jimmy "the Monk" Allegretti showed up with money on his mind:
"I remember two weeks after I started at The Chesterfield, this black Cadillac pulled up and Benny Allegretti got out with four bodyguards and walked in and took Nick to the back office. After a couple minutes they came out and cleared all the money out of the two front registers and the two back registers and then went back out to the car and pulled away."
Whether Nick Dallesandro was a mob front or an extortion target one thing was certain: he cared more for gay money than gay rights, and one early activist says that Dallesandro would not allow the Mattachine newsletter to be openly distributed at his bars.
Flint parted ways with Dallesandro after police raids on The Chesterfield and The Annex. Flint suspects that Dallesandro set him up as the fall guy in a bid to save the liquor licenses, and in The Boy From Peoria expounds as follows:
Flint said he would go to court and everybody else would be found not guilty. "However, they wouldn't find me not guilty. They kept filing it and reinstating it. I think they [the Dallesandros] were trying to say that I was really soliciting for prostitution. They were using me, trying to bargain me through the court system as a way to find me guilty so I'd be gone. Then they could say, 'Hey, the bartender who was a bad element is gone, we didn't know what was going on.' In that way they could reopen. "They were trying to use me as the scapegoat to get the bar license back after the raids."
Flint moved on to the popular cruise bar Sam's which was owned by brothers Walter (Wally) and Julius (Jerry) Fleischmann. The pair also reportedly owned the Man's World bathhouse. One bar patron from those days says the Fleischmann brothers "were considered part of the Mafia by most people." The two brothers testified about police payoffs at a 1973 federal trial which brought down nearly two dozen vice cops from the 18th District who targeted gay venues in a shakedown scheme, and police corruption is discussed extensively in The Boy From Peoria.
Wise guys and gay men may seem like strange bedfellows but it was inevitable that from time to time they would cross swords given the pervasive role of the Mafia in the bars, and Flint recounts a roll in the hay with one supposed button man:
"I remember this one guy who used to come into Sam's. He'd been after me for six or seven weeks. He'd wait for me every night after work, but I was scared of him so I'd never go with him. He was beautiful and persistent, so one night I took him back home to the Tuscany Hotel, and that was the first night I realized there were those Outfit guys who liked gay guys. He started undressing and the first thing he did was take off his gun. I had no idea. I thought I was going to get killed."
Of course, not everyone was getting into bed with the mob. Well before the 1969 riots against the Mafia owners of the infamous Stonewall Inn in New York City some gay activists in the Windy City were refusing to play ball with the syndicate boys. Attorney Ralla Klepak represented Flint after his arrests at The Chesterfield and The Annex, and when approached by the Fleischman brothers she told them to take a hike based on mob rumors surrounding the pair:
In a 1995 interview with Jack Rinella, attorney Ralla Klepak explained: "Sam's was owned by the Fleischmann brothers …. One day one of the Fleischmann brothers came to me and said, 'We'd like you to represent us, and we’d like to put you on retainer.' I said, 'No, thank you.' They said, 'You know, name your price, you want $1,000 a month, just to be on call in case we call you?' And I said, 'No, thanks.'
"When they asked why, I said, 'Because word has it that you're a Syndicate bar, and I don't represent the Syndicate—I represent the patrons.' He said, 'Sure we can't change your mind?' I said, 'That's right, I don't want anything from you, and you can't have anything from me.'"
After Sam's closed up shop the Fleischmann brothers launched The Normandy Inn at which Flint briefly worked. However, eager to spread his wings and seeking greater riches, Flint opened up his first club The Baton in 1969 and then Redoubt in 1976. The Mafia had its extortionate hand out according to Flint:
In a 2008 interview for WTTW, the Public Broadcasting Service affiliate in Chicago, Flint told filmmakers Alexandra Silets and Dan Andries that in the early 1970s, the payoff rate was about $1,800 per month to police and $1,800 to the Mafia. "How that shifted from person to person, I don't know, but that's what I know that I handed them in two envelopes," Flint said. "I had to do that before I even had to pay my rent. Because I couldn't afford an apartment, I had to live in the basement here [the Baton]. Those were hard years back then."
Flint one day would have his revenge against the mob.
In December 1983 the feds indicted five defendants, including reputed Rush Street crew bosses Joseph "Little Caesar" DiVarco and Joseph "Big Joe" Arnold, for their alleged roles in shaking down gay bars in the Old Town and Near North Side neighborhoods. Charges were dismissed against DiVarco after his defense lawyers produced records showing that a bar from which he allegedly extorted payoffs in 1979 had gone out of business three years earlier, and three out of the other four defendants, including Arnold, were later acquitted at trial.
Taking a page from a homophobic playbook the defense strategy in part was that the gay barkeeps were not extortion targets but nervous nellies, and one lawyer told the press:
"How does anyone become a criminal because of what’s on some fag's mind? Some fruit who only in his own mind is afraid has become the subject of a federal case. A federal case should be a federal case, not a fruit parade."
Flint claims that before the trial some thug came into his bar threatening that the "bar owners they better be quiet or somebody's going to get hurt." Undeterred, Flint testified that he had stopped paying off the mob, and in 1979 received visits and calls from supposed mobsters including Joe Arnold during which they requested "safety money":
"I said no, I was not going to pay it, I was not getting involved in that. * * * Yes, I said I wasn't going to get involved because the FBI was there, and I went through this before, and I was not going to do it again."
In an FBI tape recording of a telephone call played to the jury Arnold told co-defendant Frank DeMonte "that motherfucker, he's got balls, that Jimmy Flint."
Other gay bar owners who testified at the trial included Glory Hole owner Robert Hugel, and afterwards he reportedly went into the witness protection program. Flint stayed in town notwithstanding a supposed contract on his life.
Nobody messes with Jimmy Flint, and by taking on the Chicago Outfit in the mean streets he did more for the gay community than any political activist ever did on Capitol Hill.
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Further reading that may be of interest: