The Whitey Bulger Trial

What It’s Like When a Terrifying Criminal Puts a Shotgun in Your Mouth
Murder, theft, and other wickedness.
July 25 2013 5:45 PM

The Whitey Bulger Trial


What it’s like when one of the world’s most terrifying criminals puts a shotgun in your mouth.

This courtroom sketch depicts Stephen "The Rifleman" Flemmi, upper right, on the witness stand as defendant James "Whitey" Bulger listens, seated middle, next to his defense attorney J. W. Carney Jr., seated far right, while prosecutor Fred Wyshak, standing left, questions Flemmi during Bulger's racketeering and murder trial at U.S. District Court in Boston, Friday, July 19, 2013.
This courtroom sketch depicts Stephen "The Rifleman" Flemmi, upper right, on the witness stand as defendant James "Whitey" Bulger listens, seated middle, next to his defense attorney J. W. Carney Jr., seated far right, while prosecutor Fred Wyshak, standing left, questions Flemmi during Bulger's racketeering and murder trial at U.S. District Court in Boston on July 19, 2013.

Jane Flavel Collins/AP Photo.

Stephen Flemmi’s testimony ends today not with a bang but a whiny whimper. The defense wants to portray his plea agreement as a sweetheart deal—full of glittering perks, enough to tempt Flemmi to tell the government anything it wanted to hear. So attorney Hank Brennan asks a series of questions about Flemmi’s prison conditions.

Seth Stevenson Seth Stevenson

Seth Stevenson is a frequent contributor to Slate. He is the author of Grounded: A Down to Earth Journey Around the World.

“This is the Club Med of federal facilities?” asks Brennan.

“You really think so?” chuckles Flemmi. “No, it isn’t.”

“You get rib steak?”

“If I fed some of that food to my dog, he would bite me,” says Flemmi. His dog? Wait, is he allowed a dog in prison? That does seems unfair, given that certain people’s condo boards don’t allow dogs.


“On Memorial Day and the Fourth of July, do you get to celebrate with hamburgers?” asks Brennan.

“You know something?” says Flemmi, his indignation still simmering. “The hamburgers were burnt.”

Brennan also suggests that prisoners in Flemmi’s facility can watch HBO and Showtime. Which again perturbs me, as I don’t have basic cable.

The defense’s final line of questions for Flemmi zeroes in on Pat Nee—a shadowy presence throughout this trial. Nee is the Zelig of the Whitey Bulger saga. Witnesses have placed him on the scene during various murders and other criminal exploits. Yet he remains a free man. So free, in fact, that he’s poised to appear in a Discovery Channel reality show about Boston gangsters. (No word on whether Flemmi can tune in to Discovery in the hoosegow.)

The defense has been threatening for days to call Nee to the stand. The prosecution keeps saying, in effect, “Fine, go right ahead, he’s just gonna take the Fifth.” Of course he is—he’s not crazy enough to implicate himself in murders, which have no statute of limitation. But the defense’s entire case thus far has been more style than substance. Why change tacks now? Might as well drag Nee down to the courthouse and see if fireworks ensue.

With Flemmi done—carted back to his maximum-security lair, one hopes never to be heard from again—the prosecution calls Kevin O’Neil, a Southie guy whose life was entwined with Whitey’s. O’Neil is an obese mountain of a man, 64 years old, with a carbuncular nose the size, shape, and texture of a driving range golf ball. O’Neil was one of the O’s in the Triple O’s Lounge, the bar with an upstairs room that appears to have been the scene of many a Whitey shakedown.

O’Neil also owned the South Boston Liquor Mart, a charmless-looking venue with a big green shamrock painted on a wall facing a parking lot. (O’Neil refers to it as a “package store,” which is one of my favorite Masshole regionalisms. No matter where on Earth I roam, I will always say bubblah for watah fountain and packie for the place I buy my lickah.) Though Whitey didn’t work at the packie, O’Neil kept him on the payroll, cutting him checks month after month, year after year. Why was Whitey receiving this money? “He asked.” Why didn’t O’Neil say no? “I didn’t think it was smaht.”

Whitey even issued O’Neil a mortgage, though O’Neil had gotten approval from a bank. Whitey “just didn’t want to see somebody else make the money instead of him,” explains O’Neil. So Whitey loaned him $400,000 at 11.5 percent. Which sounds absurd given today’s favorable interest rate environment, but less absurd when you consider the lender owned several machine guns.

O’Neil kept sending checks to Whitey until 1997—even though Whitey went on the lam in 1994. Why? “I believed he was coming back.”

The day wraps up with Richard Buccheri on the stand. Buccheri inadvertently got himself on Whitey’s radar in the midst of some consulting he’d done regarding a property dispute. To this day Buccheri doesn’t quite understand what he did to incur Whitey’s wrath. But one day he was forced to go to South Boston for a sit-down. “It was on a Friday,” Buccheri says, clearly able to remember every chilling detail. “I called my daughter. I said I was going to South Boston, and God forbid, if something happens, you know … ”

Whitey said to Buccheri, “You know, you’re rich, but sometimes you could keep your mouth shut.” Then, the witness remembers, Whitey banged hard on the table, picked up a shotgun, and stuck it in Buccheri’s mouth. “I’m not gonna kill you now,” said Whitey, “But it’s gonna cost you 200.” Buccheri initially thought Whitey meant $200, but it was $200,000. Whitey then put down the shotgun and picked up a .45. He held it to Buccheri’s head, telling Buccheri he had 30 days to pay “or I’m gonna kill you and your family.”

Buccheri paid. He never talked to or saw Whitey again.

With the jury gone, the lawyers attend to some unfinished business. The prosecution plans to rest tomorrow, at which point the defense will begin calling its own witnesses. Many witnesses the defense had planned to bring to the stand have been declared irrelevant by Judge Denise Casper. Only a handful remain. Which means the whole trial, kit and caboodle, could be over in a week or so.

Unless Whitey talks. It’s been two decades since anyone’s heard from him. He’s been sitting here, quiet and motionless, as a parade of his old pals testifies against him. No doubt he has a lot to say.


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