James 'Whitey' Bulger

Whitey Bulger felt the same way about drugs as he did about alcohol: people who used narcotics were weak and untrustworthy.  Southie folklore held up Whitey as the scourge of drug dealers, proclaiming that for all his alleged crimes, he kept the streets of South Boston safe from drugs.  In fact, nothing was farther from the truth.  Drug sales and drug use in Southie escalated after the fall of the Angiulo organization, and Bulger got a piece of every transaction that went down on his home turf.  At a time when cocaine, or "Santa Claus" as it was called in Southie, was the drug of choice in America, Whitey Bulger made it known that every dealer in the neighborhoods he controlled had to pay him "rent" to operate.  If they refused or got caught trying to sell behind his back, the penalty was harsh, and he had a pack of vicious goons ready to enforce his law.

In 1989, a South Boston drug dealer named Thomas Cahill was robbed of $125,000 in Florida while attempting to make a cocaine buy.  Cahill had been paying rent to Bulger to operate in Southie, and when he returned to Boston, Whitey sent word that he owed $40,000 in back rent.  Cahill asked Bulger to give him a break considering his misfortune, but Bulger didn't want to hear about it.  All he wanted was his money.

Bulger's enforcers advised Cahill not to defy their boss and suggested that he get a loan from a local mortgage broker named Timothy Connolly.  When the situation was explained to Connolly, he didn't like the idea of loaning money for an extortion payment, but he was eventually persuaded to arrange a second mortgage for Cahill.  Bulger should have been happy that he was going to get his money, but he wasn't.   He wanted it faster than Connolly was getting it.

In August 1989, Tim Connolly had to answer to Bulger in the back room of the Rotary Variety Store.  Bulger was furious with Connolly for what he considered disrespectful treatment.  Pulling a knife from a sheath strapped to his leg, Bulger slashed and stabbed empty cardboard boxes as he screamed obscenities at the mortgage broker.  Suddenly Bulger whipped around and held the knife to Connolly's chest, telling him that if he wanted to live, he'd have to pay $50,000 for the privilege.

Connolly, who eventually paid Bulger $35,000, was subpoenaed by state and federal investigators who had learned of the loan to Thomas Cahill.    The focus of their investigation was Bulger's drug-related activities, and Connolly agreed to cooperate, but instead of letting the DEA use him to make their case, he was handed over to the FBI for a different narcotics investigation.  Stephen Flemmi would later admit that he and Bulger had been told that Timothy Connolly was working with the government and would probably be wearing a wire when they met with him.  Cases were made, but Bulger and Flemmi escaped any indictments.  Once again, the FBI looked out for their favorite TEs.