Apprehended Irish mob boss Whitey Bulger long has been rumored to have a little sugar in his tank, and once allegedly had a fling with doomed actor Sal Mineo.
Indeed, Whitey was known as an overnight guest at the gay resort Crown and Anchor Motor Inn in Provincetown, MA when it previously was owned by Staniford A. Sorrentino and Henry D. Vara Jr., and the Winter Hill gangster's name came up during a tax evasion trial against Sorrentino in the early 1980s. A Dec. 30, 1982 article ("Witness: Inn Owner Tried Persuading Me To Clam Up") by Richard J. Donnolly from The Boston Globe states:
The operator of a Provincetown inn, accused of "skimming" receipts to avoid taxes, used the name of a reputed organized crime figure in an attempt to discourage a former employee from becoming a major government witness, according to testimony yesterday in US District Court in Boston. The name of James J. (Whitey) Bulger, 53, of South Boston, who allegedly has been associated with Somerville's Winter Hill gang, emerged during testimony by Robert Hedrick, former general manager of the Crown and Anchor Motor Inn, Inc. in Provincetown. Hedrick was the first witness against Staniford A. Sorrentino, 52, co-owner of the inn, who is on trial before US Chief Judge Andrew A. Caffrey and a jury of 16 on charges of income tax evasion and signing false and fraudulent corporate tax returns. Sorrentino's partner in the inn has been identified as Henry D. Vara of Newton, who operates a number of gay bars. Sorrentino's attorney, Francis J. DiMento, questioned Hedrick about his claims that Sorrentino had told him that "Whitey Bulger takes care of people who open their mouths" and that Sorrentino had offered Hedrick $20,000 "to clam up." * * * Hedrick said Bulger, whom he knew to "be inclined toward violence," had been an overnight guest at the inn and had stayed at Sorrentino's home on occasion.
Sorrentino later took the stand in his own defense, and admitted a relationship -- presumably Platonic -- with Bulger but denied invoking the gangster's name to threaten his employee. A Feb. 10, 1983 article ("P'Town Bar Owner Denies Threatening Key Witness") by Richard J. Connolly from The Boston Globe states:
Sorrentino said he never knew Bulger to be violent. "I know him as Jimmy Bulger and I enjoy his company," Sorrentino said. Earlier in the trial, while being questioned by his attorney, Francis J. DiMento, Sorrentino described Bulger as a "sensitive, intelligent, intuitive person." During yesterday's questioning by attorney Paguni, Sorrentino also denied that he ever heard that Bulger had physically attacked a man identified only as Thomas Nicoletti who had been involved with Sorrentino in a civil court case. "From the stories I heard, he attacked nobody . . . I do not believe that he touched Mr. Nicoletti," Sorrentino said. There was testimony earlier that Bulger had been an overnight guest at the Provincetown inn and had visited Sorrentino's home on occasion. Sorrentino said he met Bulger in Provincetown shortly after Sorrentino acquired ownership of the inn in the 1960s.
The jury convicted Sorrentino, and a judge sentenced him to three years; however, in 1984 Sorrentino jumped bail and fled to the Bahamas which did not extradite fugitives in tax cases. In August 1984 Henry Vara Jr. and his brother Carmine were indicted for their alleged roles in the skimming operation, and in May 1985 the pair was found not guilty after a jury trial.
Bulger also had been spotted by Boston Police Boston Police Superintendent Bob Hayden in long-standing drag queen bar Jacques in the Bay Village as reported by Peter Gelzinis for the Boston Herald. The establishment was founded by Henry Vara Sr. in 1938, and previously has been the subject of public controversy as reported by Michael Blanding for Boston Magazine.
When Bulger was still on the run Howie Carr from the Boston Herald suggested with his tongue-in-cheek humor that the FBI may want to run a photo of "Gay Whitey in cowboy hat" in its search for the fugitive: "Lifelong member of the Judy Garland fan club, often broke into tears at Jacques when 'Somewhere Over the Rainbow' came on the jukebox. Recently spotted in UK karaoke bars lip-synching such Village People standards as 'YMCA' and 'In the Navy.'"
In his book The Brothers Bulger, Carr alleges that Whitey got his start in the criminal underworld as a teen after a lesbian pimp recruited him to hustle out of gay bars:
According to survivors of the era, Whitey worked out of a couple of gay bars on Stuart Street, primarily a joint called Mario's, which was also known as the Sail Aweigh. As a young male hustler, he quickly became adept at rolling his tricks--his police record indicates an arrest for "unarmed robbery" on March 18, 1947. Another of his favorite pickup spots was the Punch Bowl, which was frequently raided by the Vice Squad. * * * Whitey may have been hustling to raise some spending money, but he never was exclusively homosexual.
Bulger's sexual proclivities and any role in gay bars certainly are relevant questions to raise with his capture. The Winter Hill gangster allegedly corrupted the FBI's field office in Boston including former special agent H. Paul Rico whom he first met "in the gay bars of Bay Village in the early 1950s" when still just little more than a hustling juvenile delinquent as reported by Howie Carr for the Boston Herald.