When The Feds Moved In, Whitey Slipped Away

This article is more than 11 years old.
    A 1994 photograph of James "Whitey" Bulger, left, and two age-enhanced photographs produced in 2008, appear on the FBI's list of 10 most wanted fugitives.
A 1994 photograph of James "Whitey" Bulger, left, and two age-enhanced photographs produced in 2008, appear on the FBI's list of 10 most wanted fugitives.

Fifteen years ago tonight, I stood shivering on the sidewalk in front of the old federal court house in Post Office Square, awaiting the return of the abortion clinic killer, John Salvi. A few days earlier, he'd shot his way through two Brookline clinics, murdering two receptionists and injuring five others before fleeing to Virginia, where he shot into another clinic but was arrested.

Now a biting wind and a fast-moving fleet of cops were bringing him back. What I didn’t know as the car carrying Salvi screamed through the square and down into the courthouse garage, throwing sparks as it bottomed on the pavement, was that just a few blocks away another, bigger story was breaking. Arrest warrants were out for James "Whitey" Bulger and his crew.

"The plan was we would target Stevie (Flemmi), the bureau (FBI) would concentrate on Frank Salemme, and they also indicated they would be able to locate Jimmy Bulger," State Police Maj. Tom Duffy later told me.

Teamed up with the DEA, the state police had finally built the case against Bulger and what came to be called the Bulger Mob. Thirty-nine years had passed since Bulger's last arrest. From bank robberies he had bumped up to bigger venues. And he'd beaten every attempt by the Staties and the DEA and some Boston cops to bust him. They had long suspected the FBI of protecting him. But now their case was solid and they seemed to be closing in.

Down at 200 High Street, just blocks from the courthouse, Duffy and his crew had spent the whole day watching Schooner's Restaurant, a closed business that Flemmi's sons were renovating. Forever inseparable from the nickname "The Rifleman," Stephen Flemmi played the role of Sundance to Butch, Frack to Frick and Jeff to Mutt when it came to Bulger. He was considered the link between the Mafia and the Irish Mob of which Bulger was reputed Godfather. As such, Flemmi was the key to secret racketeering indictments that were about to be unsealed against Flemmi, Whitey Bulger and Mafia don Frank Salemme.

A 1994 photograph of Bulger appears on the Massachusetts state police most wanted list.
A 1994 photograph of Bulger appears on the Massachusetts state police most wanted list.

Ten days had passed since the federal grand jury had handed up the indictments. Fearing that Bulger and Flemmi would be tipped off, as they'd been tipped to investigations in the past, the state police and the DEA were working cooperatively with the FBI to bring them in before the word got out. The FBI insisted on handling Bulger's arrest, according to the state police and the federal prosecutor.

What happened to Salemme? The FBI was even using a plane.

"At some point, they lost him," Duffy said.

In fact, Salemme was already running when the bureau lost him.

"Stevie tipped Frank. That’s why Salemme left that day to Providence, then to Florida."

As for Bulger, the question that day was the same as it is now. "Where's Whitey?"

The bureau had told the state police and the DEA it could locate him, but Bulger had already learned of the indictments, and the word had come from within the FBI. According to a federal prosecutor several years later, the No. 2 agent in the office had told retired agent John Connolly, the one-time star, and Connolly then contacted Bulger's lieutenant to warn Bulger and Flemmi. Bulger had been on the road since the last week of December.

By staying around Boston, Flemmi was playing with fire. But after a long day on the 5th, the state cops still hadn't found him. Before breaking off that night, they played a hunch and decided to stick it out for one more hour.

That's when Duffy, who was walking on the street, saw Flemmi and a woman companion walk out of Schooners and get into a car. The car team followed, boxed Flemmi's car in and rushed it with guns drawn. Flemmi dumped some fake IDs before DEA agent Dan Doherty put a gun to his head. If anything, Flemmi was relieved to discover it was only the cops.

While Flemmi was being booked at the bureau, Duffy observed how relaxed he appeared, confident nothing would come of his arrest. But Flemmi knew what Duffy didn’t: that for close to 30 years he’d been a secret and protected top echelon FBI informant and so too had Whitey Bulger.

Agent John Connolly had been their handler. Given all the protection, the gifts he'd given to agents, the dinners and favors they'd shared, Flemmi thought he was among friends.

But where was Bulger? Getting the biggest target of all was the job of the bureau.

Duffy recalled the line that stuck with the state/DEA team years later.

"The bureau said 'we have Bulger in pocket', that they had Jimmy in pocket."

"Those words ring a little hollow all these years later," I commented.

"He's still not in pocket," Duffy replied.

Now, five more years have passed, with no evidence the FBI has ever come close.

And so, on the eve of Twelfth Night, Boston observes its own yearly anniversary.

As the Christian world marks the coming of the three wise men, the Magi, we think of the three wise guys, and the one who got away.

This program aired on January 5, 2010. The audio for this program is not available.

David Boeri Twitter Senior Reporter
Now retired, David Boeri was a senior reporter at WBUR.