Of course a place nicknamed Brew City had to have gay bars even during the 1950s. The FBI identified the following "homosexual hangouts" in Milwaukee, WI according to a 1959 report: The Clifton Bar at 336 West Juneau; The Royal Hotel Bar at 5th and Michigan Street; The White Horse Inn at 1426 North 11th Street; The Riviera Bar at 401 North Plankington Avenue; and The Wildwood Bar, a "colored lesbian hangout," at 1420 West Walnut Street. However, like in most American cities at this time, it apparently was necessary for a gay bar to have the "proper protection" -- i.e., making payoffs -- in order to operate without police molestation.
One gay bar which did not have the "proper protection" was the Pink Glove at 631 North Broadway according to a July 1958 FBI report concerning its closure by Milwaukee cops:
Information has been developed that the "Pink Glove" Cocktail Lounge has had its license revoked by the Milwaukee PD because it has gained the reputation of being a "fag" hangout; that is, being patronized by queers and sex perverts. This cocktail lounge was licensed to [name redacted] although it is believed that [name redacted] had a financial interest in it. The cocktail lounge is now "for sale" and [name redacted] owner of the popular Jordan's Restaurant on North Water Street, is believed to be interested in purchasing it. Jordan's Restaurant caters to the sporting crowd on Milwaukee's financial row - North Water Street. [Name redacted] has been heard to have said that the reason the Milwaukee PD closed the "Pink Glove" is because he did not have the proper "protection."
The watering hole did not have a long life as a gay bar. The license holder for the Pink Glove was Marvin Klein, and it previously had operated as Phillips Cocktail Lounge. However, according to FBI files, "this cocktail lounge was recently leased or in some manner the [name redacted] took in partners who are homosexuals with the resultant change in the name of the cocktail lounge to the Pink Glove, which in a matter of weeks became so notorious as a hangout for homosexuals in Milwaukee that the Milwaukee Police Department has been literally forced to close the place up."
Marvin's two brothers Harold and Bernard were suspected racketeers with various interests in coin-operated machines, waste carting and salvage, and bars and booze, and had alleged ties to reputed hoodlums including the DiMaggio brothers, Isadore Pogrob and Jack Enea. Even in Brew City the underworld was a violent life. Enea was gunned down in November 1955, and Pogrob gunned down in January 1960. Notwithstanding some suspicion about their dealings the Klein brothers never were convicted of any crimes. Harold and Bernard were charged in 1962 of receiving stolen property but acquitted amid accusations of intimidating a prosecution witness.
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