Bulger Day 24: Stephen Flemmi Describes His Girlfriend’s Murder

Whitey Bulger's old associate described the death of Debra Davis and several other alleged Bulger victims.

“It’s going to affect me until the day I die,” says Stephen Flemmi of his decision to let his former partner Whitey Bulger murder his girlfriend Debra Davis.

Flemmi’s second stint on the stand took the entire day of the Bulger trial as he detailed his entrée into criminal activities in the early 1960s, described the murders he committed through the gang wars of that decade, and finally began outlining the crimes he committed alongside Bulger. The most gruesome of them, of course, was that of Debra Davis, Flemmi’s girlfriend at the time. It’s a story we’ve heard before, but Flemmi had to tell it again: He let slip to Davis that he and Bulger often met with FBI Agent John Connolly. Davis then asked whether Connolly had information on the murder of her brother in prison, revealing that she knew about his connection to Bulger. That made Bulger mad, as did Davis’s flashy lifestyle, funded by Flemmi’s ill-gotten money. And so eventually he convinced Flemmi that she had to go, inviting her to a house in South Boston where, according to Flemmi, Bulger strangled her as he brought her down the stairs, then left Flemmi and the others to dispose of her body while he went upstairs to lie down.

Flemmi, 79, is in federal prison having pled guilty to several murders in order to avoid the death penalty as well as an assortment of other racketeering charges and the like. He began the day describing how he befriended Bulger upon his own return from Canada, where he’d been avoiding a murder investigation for several years. He got along with Bulger, he noted,  because both abstained from drinking and smoking and enjoyed exercising. He then took the jury through several other murders, including that of Eddie Connors, whom he shot up in a phone booth for telling people about another murder the gang had committed.

The testimony contained the occasional spate of darkly comic moments, as when Assistant U.S. Attorney Fred Wyshak asked Flemmi where exactly he shot one victims. “In the head,” Flemmi replied, prompting a laugh from Wyshak who clarified, “Okay, what was the location?” “Oh,” Flemmi said, “in the garage, over in Roxbury.” In contrast to the vulgar greetings he and Bulger had for each other at their reunion yesterday, the testimony seemed to go without a hitch, as Bulger mostly took notes or avoided eye contact with the witness, and Flemmi mostly delivered his testimony with a disconcerting lack of emotion. Look forward to more of this next week, likely to be the final one for the government’s case.