The evidence that finally brought criminal charges against Whitey Bulger came to investigators by
chance, and it had been languishing in file cabinets for over ten years before it was used. In 1983, the
Massachusetts State Police bugged Heller's Café in Chelsea, believing that it was a "bookmakers' bank"
where checks from losing gamblers were cashed and money was laundered. Bookies from all over the Boston
area congregated there to conduct business, and state police investigators listened in on conversations
that revealed the inner workings of an enormous illegal gambling operation. According to the Boston
Globe, they learned that Michael London, the owner of Heller's, washed $50 million a year, and ace
oddsmaker Burton "Chico" Krantz took in over a million dollars a week. But along with the hard information
about the illegal gambling industry, the investigators also heard some very interesting shop talk,
particularly the bookies' gripes about having to pay rent to either the Mafia or Whitey Bulger and Stephen
Flemmi. None of them liked the situation, but nearly all of them complained about it, and the state police
got it all down on tape. It was solid evidence that Bulger and Flemmi were extortionists.
The bookies were rounded up, and the U.S. Attorney's office came up with a unique strategy for putting
their feet to the fire. In addition to charging them with illegal gambling, the bookies from Heller's Café
were charged with money-laundering. Instead of the expected legal slap on the wrist, the bookies were now
facing the possibility of long sentences in federal facilities. One by one, they began to make deals with
the government, offering to cooperate in ongoing investigations against organized crime in Boston in
exchange for leniency.
Years later, in August 1990, 51 individuals involved in a Southie cocaine ring were charged as a result
of a 15-month DEA investigation. Bulger was not charged, but members of his crew were. True to their
Southie roots, Bulger's henchmen refused to snitch on their boss, but the indictments exploded the myth
that Whitey Bulger kept drugs off the streets of South Boston.
Around this time, Tim Connolly, the mortgage broker who had been threatened at knifepoint by Bulger and
waylaid by the FBI, went to the U.S. Attorney's office out of desperation. Fearing for his life, he offered
to wear a wire and testify against Bulger.
Little by little, over a period of nearly twelve years, authorities gathered enough evidence to charge
Bulger, Flemmi, and Boston Mafia chieftain "Cadillac Frank" Salemme with racketeering and extortion.
Authorities decided that all three would be arrested simultaneously, fearing that they would flee if they
learned that any one of them had been apprehended. Unfortunately, the arrests didn't play out the way the
authorities had hoped. On January 5, 1995, Flemmi was taken into custody without a glitch, but it took
seven months to find Frank Salemme in Florida. Bulger disappeared completely.