Happy 90th birthday to Stephen ‘The Rifleman’ Flemmi, Boston’s most prolific serial killer

Stevie Flemmi, the most prolific serial killer in Boston history, turns 90 years old today.

As a lifelong snitch for the G-men, Whitey Bulger’s geriatric gangster partner will be celebrating, if that’s the right word, at an undisclosed rats-only federal prison in parts unknown.

Even though you won’t find his name listed on the Bureau of Prisons website, Flemmi is not going anywhere, ever, not after murdering 50 people.

Those 50 murders seem even more staggering when you consider that Stevie has been locked up since early 1995. So he committed 50 murders in his first 60 years.

Now he’s serving two life terms, plus 30 years. Three years ago, he unsuccessfully sought “compassionate relief” from yet another life sentence, in Florida, for a 1982 contract hit in Miami.

But even if he’d gotten lucky in Florida, Flemmi would still be doing life on an Oklahoma conviction for a 1981 murder, not to mention life for 10 more murders here in Massachusetts.

The only time Flemmi left prison was when he testified against other gangsters. But those days are over now because everyone he could have ratted out is dead.

On what was probably his final snitch assignment back to Boston in 2018, Stevie was asked on cross-examination how many murders he’d been involved in. It took him a while to add everything up in his head.

“Probably about 50,” he finally said, “either as an actual participant or the conspiratorial aspect.”

Flemmi was testifying against another of his old partners, Cadillac Frank Salemme, in a trial involving a 1993 murder of a nightclub owner.

“Look at him,” Frank whispered to reporters one day during a recess. “He still thinks he’s getting out. That’s what he’s told people.”

For the record, Frank Salemme never made it out. He was convicted of that murder and died at a federal prison hospital in Springfield MO in December 2022. He was 87.

Salemme’s younger brother Jack died a couple of weeks ago at age 81. They’re dead now, almost all of the old-time Boston gangsters, except the one wise guy who killed more people than any of them.

At that 2018 trial, Stevie talked even more haltingly than he used to. Salemme thought he’d had a stroke. But Flemmi could still recite some doggerel about life on the street.

“If you’re broke/You’re a joke,” Flemmi said with a smile. “If you have money/You are funny.”

As Salemme once told a Congressional committee, “There’s two things with Flemmi paramount to everything, his money and his women. That was his M.O. all along. His money and his women, not necessarily in that order.”

Not that he’s had any of either since January 1995, when the FBI finally arrested him after all the killing and the snitching and the payoffs to the six Boston agents.

“Is this a gag?” Flemmi said in disbelief as the G-men handcuffed him, 50 murders too late.

Like Whitey Bulger, Stevie was a serial killer. The two of them were a murder machine, and everyone in their crew had his own specialized role.

Bulger handled the actual killing, and Kevin “Two” Weeks dug the holes for the bodies. A guy named Phil Costas always brought over bags of quicklime to make the victims’ flesh decompose more quickly.

Stevie’s assigned task was pulling the teeth out of the corpses, to foil identification if the cops ever dug up the bodies.

At first he relied on a standard pair of pliers, but they got rusty. And once they started killing women the pliers were too big anyway for their smaller mouths.

So Whitey had his girlfriend, a dental hygienist, order a state-of-the-art pair of tooth extractors from her dentist boss’ supply catalogue.

Merry Christmas Stevie!

Anything to improve efficiency on the homicide assembly line.

Stevie used his new dental equipment on both his 26-year-old girlfriends. Deb Hussey, his “stepdaughter,” represented a particularly tough extraction, he testified.

“I couldn’t go through with it. I started to and pulled a few teeth out, I tried to anyway.”

Then there was his other 26-year-old girlfriend, Deb Davis. He didn’t deny pulling out all of her teeth.

But Whitey’s lawyer then asked him if he’d then pounded Davis’ bloody teeth into dust, so that they could never be used as evidence against the two fiends who’d strangled her.

“I didn’t smash her teeth up!” Stevie yelled at Whitey’s public defender. “Show me where it says that I smashed her teeth with a hammer! You make that accusation, please respond to it. I didn’t smash her teeth out with a hammer.”

After killing both Debs, Flemmi went to their mothers and told them that he would hire private detectives to find the 26-year-olds. In other words, he lied.

“I couldn’t very well say I’d done it,” he explained in 2018, as Salemme sat shaking his head in disgust. Stevie was always crying, Salemme testified. He described the waterworks as “Stevie’s dog-and-pony show.”

In 2013, at Whitey’s trial, Flemmi elaborated on the lies about private detectives. Was it a cover up? the lawyer asked.

“It’s all part of the cover up, yes. When you commit a murder, you cover up on it, you don’t admit it to people. I don’t know if you’re aware of that, you should be, you’re an attorney.”

Now Stevie is locked up in parts unknown, in what’s called Witsec (for Witness Security) program. During Stevie’s stool-pigeon performances against his (very) old pals, the defense lawyers usually tried to convince the juries that Stevie’s living large in Club Fed.

“You have a store at your prison that doubles as a delicatessen?”

“That,” replied Flemmi, “is absolutely ridiculous.”

“Can you get rib-eye steak?”

“If I gave some of that food to my dog, he’d bite me.”

Testifying at yet another Mob murder trial, in Florida, involving corrupt FBI agent Zip Connolly, Flemmi was asked if he ever dreamed of walking out of prison a free man.

“I don’t know what the future holds,” Birthday Boy said. “Everybody hopes at some point in the future something beneficial would happen.”

“I’m not asking about everybody,” the lawyer said. “I’m talking about you. Do you hope, Mr. Flemmi?”

“I’m still alive,” he said. “There’s always a hope. You never know.”

You do know, Stevie. There is no hope whatsoever. But at least at the age of 90, you can still enjoy a rib-eye steak dinner for your birthday this evening.

Only the good die young.