Betrayal: Whitey Bulger and the FBI Agent Who Fought to Bring Him Down (9 page)

“We’re going to close this guy.”

“No, you’re not.”

“What do you mean?”

“You’ll never close Bulger.”

As I drove back with John Connolly to Boston’s Federal Building, I knew exactly what I needed to do: close Whitey Bulger and put the Boston office back on track, no matter how many names I had to take or asses I had to kick.

9

BOSTON, 1951

To understand exactly how and where order and discipline had come apart in the Boston office of the Bureau, you’d need to go all the way back to 1951 when Special Agents Paul Rico and Dennis Condon joined the FBI. They came to duty in the wake of World War II, before the onset of Korea, at a time when the country remained hungry for heroes and the FBI under J. Edgar Hoover was more than happy to oblige. The agency was, after all, the glorious domestic protector and enforcer that had kept the country safe from foreign and homegrown spies alike. While America was helping to rebuild Germany and Japan from the ravages of war, the Bureau needed a new enemy with new G-men heroes to sustain its image and prove its usefulness to society. Slick and ambitious, Rico and Condon were more than happy to step into the spotlight.

At the same time, a juvenile thug named Joseph Barboza was lining his pockets with cash from petty thefts and beginning to make his presence known around Boston with a string of strong-arm burglaries. At seventeen years of age, he was already on his way to prison for the first time. By 1954, within weeks of his escape from Walpole State Prison, Barboza reached the criminal big time with a string of local armed robberies, kidnappings, and extortion. Many who knew Barboza described him as a smart kid, but his harsh features belied that. Those features included a massive, jutting jaw; a ridged, Simian-like forehead; and protruding cheekbones that cast shadows over the lower half of his face. People were known to cross to the other side of the street when they saw him coming; Barboza was that intimidating and that repulsive.

James “Whitey” Bulger’s ascent through the ranks pretty much mirrored Barboza’s during this period. Like Barboza, he was involved in armed robbery and numerous assaults, according to the local police blotters. And, like Barboza, he was described as a bright but extremely dangerous kid: unstable, vicious, and utterly without conscience. Unlike Barboza, though, people didn’t cross the street to avoid him. Early descriptions, in fact, depict Whitey as “cute with a wry smile” that belied his true intentions, and a “capacious appetite” for violence that knew no bounds.

During his stretch inside Leavenworth, the prison psychiatrists tagged Bulger with a “sociopathic” personality—the same label they would give Barboza in the years to come. But even the simplest of local residents in and around Boston recognized both Barboza and Bulger for what they were: stone killers.

When I lectured at the FBI Academy and at law enforcement agencies around the country, one of my specialties was abnormal psychology, allowing me to profile the masks of sanity that men like Barboza and Bulger wore. Whether they were deemed psychopaths or sociopaths, criminals like Bulger and Barboza represented an entirely different species that we were just beginning to understand. These men, whose vicious behavior propelled them through the gang ranks in the fifties and sixties, exemplified the type with whom the FBI, inexplicably, decided to do business.

Well, maybe not so inexplicably.

In 1961, Attorney General Robert Kennedy listed New England’s mafia chief, Raymond Patriarca, as “one of the thirty-nine top echelon racketeers in the country,” set to be targeted for FBI investigation and prosecution by Kennedy’s office. Director Hoover took Kennedy’s baton and ordered each field office to infiltrate “top echelon organized crime groups” with FBI informants. Thus, on June 21, 1961, the Top Echelon Criminal Informant Program (TECIP) was formed to ensure the success of the FBI attack against organized crime racketeers. In addition to these informants, the Bureau was beginning to employ early electronic microphone surveillance (“misur”), which Organized Crime units later dubbed the “black bag” bug.

The Bureau had found the new enemy it needed and new means, along with new heroes, to fight it. By 1963, Rico and Condon were having moderate success in Boston with the microphone surveillance information, anonymously encoded in Patriarca’s case as BS-856C (Boston 856 Confidential). BS-856C was actually an illegal, non-court-ordered microphone surveillance that surreptitiously and electronically captured information from the mafia gangsters. This “tin ear” morphed into a “live ear” through its use by informants wearing what is now referred to as a “wire.”

Whatever you call it, this new tool was very effective in gaining unique and raw insight into the mafia’s organizational structure and operations, so that the Bureau’s response could be appropriately mapped out. The technology was so cutting edge at the time that there were some questions as to whether these wires were legal or not, but back then they were seen as the only means to combat an organized crime entity whose power was growing unchecked.

Jerry Angiulo, the underboss of Boston underworld rackets, as well as his chief lieutenants and his boss Raymond Patriarca himself, were the initial targets when the new surveillance system went into operation. And the effectiveness of the misur and informant program was proven early on. In 1964, a hood by the name of Frank Benjamin was murdered, and Vincent Flemmi, aka The Butcher, was the prime suspect.

“All I want to do is kill people,” Flemmi explained to an associate over Condon’s tin ear surveillance tape. “You can leave hitting banks to somebody else, ’less I get to go in blasting.”

A shocking revelation in all respects. By this time, Condon and Rico had managed to turn Joseph Barboza into an informant, allowing him to avoid a life sentence on yet another murder rap. Whether they actually had the evidence to make the case stick became a moot point, since the new surveillance techniques had been enough to turn Barboza. Barboza claimed that “Flemmi had killed Benjamin and cut off his head.” His assertion was independently verified through a wire intercept, as the relentless capacity for bragging by thugs everywhere found a counterbalance in electronic surveillance. Wiseguys loved to talk, and such constant boasting of their own brutal conquests often led to their ultimate undoing. They could no longer kill with impunity. Thanks to the FBI’s new surveillance techniques and technology, the rules of investigation were changing.

The tin ear in question revealed particularly grisly stuff: Vincent Flemmi wanted to be the “contract man” in Boston; he talked about a number of killings, admitting that he murdered Benjamin and boasting about cutting off his head. Procedure, and protocol, inside the FBI was changed forever as both the electronic surveillance and TECIP programs, engineered in Boston in large part by Rico and Condon, were expanded nationwide.

Rico notified FBIHQ that Vincent Flemmi wanted to be the best hit man in Boston, which, Rico believed, could eventually make Flemmi the best informant. In 1964, Rico told the FBIHQ that Flemmi wanted to kill Teddy Deegan, a small-time hood, because he “owes us money, about $300, and is welching on the deal.” The threat by Vinnie Flemmi got back to Deegan, who vehemently denied Flemmi’s allegation, telling his Irish mob friends that Flemmi was just out to kill him. Even with that threat on the books, along with everything else on the wire, Flemmi was targeted as an informant by Boston FBI, just as Joseph Barboza had been before him.

But even their Boston mob associates recognized that Flemmi and Barboza were taking things too far.

“People are afraid of Flemmi and Barboza,” New England crime boss Raymond Patriarca was told one day in Providence. “You gotta shut them down.”

The word Patriarca put out must never have reached Barboza and Flemmi, because their killing spree continued. Either that or they simply didn’t care and disregarded the order from their boss. Besides, they had their next target already picked out.

Teddy Deegan was described by the Irish guys as a “pain in the ass.” He was a wannabe whose reputation as a lowlife upset his friends. Always hustling for dough, Teddy frequented a number of bars including the Ebb Tide (informant Richie Castucci’s place in later years), where one night Barboza and Flemmi lay in wait for him outside. When Deegan emerged through a side exit into an alley, they gunned him down.

The tin ear told Rico and Condon that a notorious hit man called the “Animal” had gotten permission from mafia boss Patriarca to whack Deegan. They made Barboza out as the Animal and they were right. Barboza confessed but refused to name Flemmi. Without any other way of nailing him, the agents were left with an informant they didn’t want to put away and a stone-ass killer they couldn’t. Believing they had no other choice, Rico and Condon sat passively by while four other suspects were arrested for the Deegan murder. Those same suspects were later convicted in large part due to Barboza’s sworn, and perjured, testimony. Rico and Condon neither said nor did anything to prevent the wrongful convictions. The two agents had inarguably crossed an ethical line and, while they might have been the first, they were far from the last.

For his part, Barboza had played the agents perfectly. He had implicated the subjects due to a grudge he’d held against one of them, Joseph Salvati. The FBI had offered the Animal a perfect means to get even over a perceived debt, enabling him to settle his score. He’d gotten away with Teddy Deegan’s murder and then helped get Salvati and his gang put away for it. It was a saavy and effective move by Barboza, leaving a pair of top-flight FBI agents totally beholden to him.

Agents Rico and Condon had occasion to visit another wiseguy, Frank “Cadillac” Salemme, in an attempt to develop him as an informant as well. They’d meet regularly in his garage for doughnuts and coffee and do little more than “shoot the shit.” Salemme was an aspiring mob boss who loved busting Condon’s balls about backing Joseph “the Animal” Barboza’s perjured testimony on the Deegan killing. The inside mob joke was that the FBI was protecting Barboza for no other reason than they could. No one on the street really believed that Barboza was a reliable FBI informant, except for the FBI.

After all, Barboza was little more than a brutal killer who viewed his own informant status as a license to murder without fear of repercussion. He’d mastered the game of keeping his handlers, Rico and Condon, dependent on him for information that he invariably hinted at but never delivered, at least not in full. Like many future informants, he was the one calling the shots when it should have been quite the opposite. He was the figurative fox in the FBI henhouse, which didn’t stop Rico and Condon from trying to turn the equally brutal Salemme into an informant as well.

“You’re a fucking Catholic, right?” Salemme taunted.

“Sure,” said Condon.

“Fucking Catholic and royal fucking Knight of Columbus, and that doesn’t stop you from putting four muffs on death row for crimes they didn’t do.”

Salemme seemed to find the whole thing sadistically amusing and was clearly busting Condon’s balls. Salemme, of course, had no idea at the time that Barboza and Vincent Flemmi were FBI snitches, and that Flemmi had become a Top Echelon informant, a kind of dark knight for Condon and Rico.

In the bullpen back in the FBI office, agents Rico and Condon had become the “big cheese” in the Organized Crime squad bay, the inside joke being that you need “big cheese” to take care of “salami” and his pals. They’d become new heroes for a new age. Their handling of TEs and other informants gained them stature at FBIHQ and assured the manpower and resources necessary for continuing the agents’ fight against the mafia. Their work received compliments from the Strike Force, the U.S. Attorney’s Office, and even the Department of Justice. Using their high-powered informants they were able to turn a whole chain of wannabes into “squeals,” furthering the FBI effort to penetrate the myriad factions of organized crime mobs throughout New England in keeping with the stated goals of headquarters.

The problem that would come back to haunt the Bureau again and again was that few people inside and outside the FBI actually knew who these informants were. Only symbols and numbers were used to identify them, and the refusal to name informants, under any circumstances, became sacrosanct. The worst sin in the church of the FBI was to reveal an informant’s identity, even in a court of law. They were to be protected at all costs, even if that meant ignoring actions totally out of step with existing law.

Information gleaned from squeals trumped everything else, regardless of how much it actually yielded. There was always tomorrow went the thinking, and after investing so much time and resources into the effort of building them up, no agent was going to close down his own informants. Everything seemed upside down. In Boston, for example, Top Echelon informants like Barboza and Flemmi were targeted against major players in the Angiulo and Patriarca crime families throughout New England. That was enough to let anything and everything else go. Having serious, self-serving bad guys working directly with the FBI, though, represented a remarkable sea change and an exceedingly dangerous one.

These mob informants, especially the TEs, gained efficacy with each successful prosecution produced by the intelligence they provided. As a result, their value to the FBI provided them with a safety net, and as it became apparent that they could conduct their business without fear of prosecution, they became increasingly violent. The FBI understandably did not want altar boys. But neither could they have wanted the violent, irredeemable criminal element that could not be trusted. In fact, agents were finding that it became easy to turn the worst of the worst precisely because it facilitated their ability to do business unencumbered by fear of arrest or prosecution. This also spawned the “getting on the bus” syndrome that insidiously encouraged many informants to lie and fabricate their tales based on secret, inside information wittingly or unwittingly furnished to them by their enforcement handlers.