Tales from the Whitey watch

Former DEA agent recounts 2 years of stealth, frustrations

James ‘‘Whitey’’ Bulger (left) and Kevin J. Weeks in South Boston during surveillance by the Drug Enforcement Administration and Boston Police. (Mike Swidwinski/ Retired DEA special agent/ 1989)

They tracked him any way they could, watching him through binoculars, bugging his Ford Crown Victoria, flying over him in a Cessna plane to pick up his conversations, or trying to intercept them with an antenna atop the Dorchester Heights Memorial in South Boston.

It was a two-year game of cat and mouse, as federal investigators monitored the movements of gangster James "Whitey" Bulger and his lieutenants in a frustrating quest to snare him for extorting profits from drug dealers in the neighborhood.

The investigation by the DEA and Boston Police led to federal cocaine charges against 51 people in 1990, but no charges against Bulger.

For the first time, in an interview this week with the Globe, a Drug Enforcement Administration agent assigned to the investigation 18 years ago told of the twists, turns, dramatic encounters, and disappointments of the chase.

Mike Swidwinski, a retired special agent now living in Michigan, also provided never-before-published photos that he took of Bulger, Stephen "The Rifleman" Flemmi, and Kevin J. Weeks from 1989, saying the public should see them and know the story behind them, because it is part of the city's history.

The surveillance photos provide rare glimpses of Bulger, now on the FBI's 10 Most Wanted list, patting a dog on the head near Columbia Park, holding forth at Castle Island, and relaxing on lounge chairs with Flemmi and Weeks at a time when they ran a criminal enterprise in Boston that rivaled that of the Mafia.

Swidwinski's candid account shows what it was like to be on the other side of the Bulger gang, sometimes stealthily watching, other times coming face to face with their prey.

"In retrospect, a lot of us didn't know what a dangerous man he was," said Swidwinski, who had just five years with the DEA at the time of the surveillance operation.

Bulger, 77, a longtime FBI informant, was indicted in 1995 on federal racketeering charges but fled just before the indictment and has been a fugitive since . He is also charged with 19 murders. Flemmi, also a longtime FBI informant, is serving a life sentence for 10 murders and is currently cooperating with the government.

Investigators involved in the surveillance operation, including Swidwinski, were always suspicious that the FBI hindered their attempts to get Bulger.

Bulger's longtime handler, John J. Connolly Jr., was convicted of racketeering in 2002 for protecting Bulger and Flemmi from prosecution and leaking them information. However, Connolly was never charged with compromising the 1989 DEA investigation, and Weeks told the Globe this week that it was obvious they were being watched during that period.

Swidwinski said the Bulger investigation "was a piece of history that we actually participated in" and, with Bulger still on the run, the case is "sort of an unfinished memory" for him.

Swidwinski and his partner were trying to quietly gather evidence to show that South Boston-based cocaine dealers were paying Bulger a cut of their profits. They tapped Bulger's cellphone (a rarity for that era) and a mailbox and even buried a bug in a patch of dirt near where he walked regularly at Castle Island.

Bulger seemed always vigilant. One time Swidwinski was parked in a van across from Columbia Park (now known as Moakley Park), watching Bulger through binoculars. Suddenly, as he focused on Bulger, he realized that Bulger was staring back at him, through his own binoculars. And then the gangster started walking toward him, with Weeks at his side. The agent quickly drove away to avoid a confrontation, he said.

Another day, after agents suspected that Bulger and his deputies had discovered a bug that had been planted inside Bulger's Crown Victoria, they went to retrieve it. They stopped Bulger during a planned traffic stop, and Swidwinski ordered Bulger out of the car.

"My only bragging rights is I think I'm the only guy in history who ever took Whitey Bulger out of a car at gunpoint," said Swidwinski, now 57, who retired two years ago after 22 years with the DEA. He remembers grabbing Bulger's car keys and looking at the key ring, which had a pendant with a devil's face on it and the words "Born to Raise Hell."

Retired Boston police sergeant detective Frank Dewan, who worked alongside Swidwinski in the investigation, recounted how one day he was following Bulger and his girlfriend, Catherine Greig, when Bulger suddenly turned and began following him. "It was cat and mouse," said Dewan, adding that it was "just to let us know that he knew we were there."

Other efforts to bug Bulger also proved unsuccessful, said Dewan, recalling how the bug planted in the ground at a Castle Island spot where the gangster often stopped to discuss business with his henchmen malfunctioned, picking up nothing but WBZ radio.

Swidwinski's description of the surveillance operation recalls a lower-tech time in law enforcement. The investigators planted a bug in Bulger's car from Dec. 21, 1989, to Jan. 19, 1990, which acted as a transmitter and sent a signal to a DEA-operated Cessna that would fly overhead, following Bulger during the day, Swidwinski said. An agent in the plane would record the conversations.

At night and during poor daytime weather conditions, DEA agents would climb to the top of the Dorchester Heights monument on Telegraph Hill with another antenna to capture Bulger's conversations as he moved around South Boston.

"The weather conditions in the middle of the winter up in that tower were just horrific," said Swidwinski.

But none of Bulger's conversations were of any value, prompting investigators to yank the bug, Swidwinski said. The agents believed that Bulger suspected his car was bugged, because when Weeks would start to talk, Bulger would warn, "I told you, don't talk in the car."

"Either he is a highly intelligent person, or he just kept getting tipped off," Swidwinski said.

Bulger always suspected he was being bugged and knew he was followed by the airplane, according to Weeks, who struck a deal with the government after his 1999 arrest and is now a free man after serving five years for assisting Bulger in five murders.

"You'd look up in the sky and see this plane doing figure-eights over us," said Weeks during a telephone interview yesterday. "We'd drive to the Cape, we'd be on the highway, and we'd see the plane."

Weeks said that he and Bulger were aware of the DEA surveillance because they had police scanners in their cars, set to the DEA's frequency. In fact, he said, he learned from listening to the scanner that agents were about to make arrests in August 1990, prompting him and Bulger to hang out at Boston Common that morning until they were sure they weren't going to be arrested.

Swidwinski has read books by Weeks and others about Bulger and surfs the Internet for updates about the international effort to catch him. He said he has no idea where Bulger might be, but if he encountered the gangster on the street, he believes he could recognize him, just from his stern and sometimes menacing voice.

"He didn't have that Boston accent," Swidwinski said. "He kind of had what I'd call a normal accent. There were times when he'd raise his voice and you could almost see the smoke coming out of his nostrils. . . . He pretty much spoke with authority."