Betrayal: Whitey Bulger and the FBI Agent Who Fought to Bring Him Down (10 page)

While Boston’s Special Agent in Charge at the time saw the reports describing the crimes committed by the infamous Barboza and Flemmi, he still wrote Director Hoover that “Special Agents Paul Rico and Dennis Condon should receive a salary increase for their fine work in handling TEs.” Hoover’s return memo applauded Rico and Condon’s handling and development of TEs in the Boston office. Emboldened by accolades from the pinnacle of FBIHQ, Rico and Condon continued their efforts to expand their stable of informants, adding Stephen Flemmi (Vincent’s brother) to the fold designated with symbol number BS (Boston) 955–C-TE (Criminal–Top Echelon) informant.

Flemmi, who was destined to become Whitey Bulger’s right-hand man, might have been reared in a family steeped in crime, but he also served as an army paratrooper, passing the rigorous training to become a sniper. Instead of endearing him to a different kind of lifestyle, the army served only to strengthen his bonds to crime. His tour added to his toughness and mystique. Like Bulger, he was only of average size. Unlike Bulger though, Flemmi quickly tired of an exhaustive physical regimen to keep himself in shape. He ended up growing a paunch and wearing his hair so long that stubborn patches would drop down over his forehead. Also like Whitey, he showcased a sexually flirtatious fondness for women, some say to hide the rumors of homosexuality that had surfaced while he was in the army. The same rumors abounded about Bulger, making some think his whole tough-guy act was a façade meant to disguise his true nature.

Praise for their efforts knew no bounds and neither did their ambitions. The TEs were giving the agents what they wanted, and the agents were giving their TEs what they needed in return. Both had clear paths to attaining power and neither could get there without the help of the other, forming an inexorable bond between cop and criminal.

People, in other words, were quite literally getting away with murder, and nobody seemed to care.

10

BOSTON, 1968

By 1968, Joseph Barboza had become the most dangerous individual known to Boston law enforcement. Obviously, he would make a great witness against La Cosa Nostra, and he was encouraged by Paul Rico and Dennis Condon to testify against Patriarca, deemed the “LCN boss and possible Commission member.”

Barboza did in fact testify, resulting in the conviction of Patriarca and his crew in federal court at Boston in 1968. Rico and Condon were crowned golden boys in the Boston office of the FBI, no longer able to do any wrong in spite of the wrongs they’d already done. They had used Barboza to work his black magic in the takedown of the Italian mafia in New England. And Barboza, in turn, had used them to absolve himself of the Teddy Deegan murder and send four innocent men to prison in his stead. Throughout that trial, Rico and Condon continually checked on Barboza’s well-being while he was in protective custody. Actually, the gangster would later claim that the feds were telling him what to say to make sure his story stuck.

Rico and Condon were in court the day the verdicts against the four men were handed down. The Boston Strike Force commented to FBIHQ that “as a result of FBI investigation in state court in Boston, four more [gangsters] are convicted in the 1965 slaying of Teddy Deegan.” Two of these were sentenced to death while Salvati and another defendant identified by Barboza got life sentences. Shortly after the convictions, commendations direct from Hoover himself at FBIHQ kept arriving, praising Rico and Condon’s work on the case. Hoover wrote the agents personally that “The successful prosecution of these subjects was a direct result of your noteworthy development of pertinent witnesses.”

But the seeds of the nefarious doings and ultimate unraveling were firmly in place. In early 1970, Condon reached out to Barboza, now living in San Francisco, to let him know his life might be in danger, something the agent had learned through another informant. The Boston office of the FBI denied that Barboza was still cooperating as an informant and refused to offer him any further help. The temperamental Barboza decided to get even by recanting his testimony that convicted the four innocent men of the murder of Teddy Deegan. He also tried to give evidence that mob boss Patriarca should be exonerated due to additional perjured testimony he provided to FBI agents and the court.

“I got enough that will convince any court that I was lying,” he said at the time, determined to make Rico and Condon pay for abandoning him.

None other than F. Lee Bailey, acting as Barboza’s attorney, reiterated that Deegan’s slayers were convicted on false testimony by Barboza and that they were innocent. By October 1970, FBIHQ was advised that witnesses in affidavits “will allege that Barboza told them he lied about Deegan, about Patriarca and others,” naming the Strike Force and the FBI itself as being responsible for his perjured testimony. F. Lee Bailey went public insisting that Barboza had similarly committed perjury against Patriarca, Angiulo, and the Deegan suspects on the prodding of his corrupt handlers, Rico and Condon. Ultimately, Bailey’s strategy accomplished nothing from a legal standpoint, while casting even more aspersions on the FBI. But Barboza was then paid at least $9,000 by the FBI on the pretext of cosmetic surgery to alter his appearance. He first disavowed his new story, the truth, only to go back to telling it to anyone who’d listen until he was shotgunned to death on a San Franciso street in 1976.

Still, the blowback resulting from their protection of Joseph Barboza as an informant at all costs would haunt both Rico and Condon for years after they retired. During the House Committee on Government Reform’s hearings in 2003, Representative Dan Burton asked Rico about his complicity in sending an innocent man to jail for over thirty years. Rico replied curtly: “What do you want from me? Tears?”

Desperate to redeem himself with the Bureau decades before then, Condon had opened another informant, James “Whitey” Bulger, whom he knew through Whitey’s brother Billy, an aspiring Boston politician. Whitey had been arrested by Condon’s partner Rico on a bank robbery charge, so all the pieces seemed to be in place. Except in his first go-round as an FBI informant, Whitey Bulger proved utterly unproductive and was closed three months later and jailed soon after that.

But Bulger’s relationship with the FBI’s Boston office was far from over. In 1973, just when the careers of Rico and Condon were winding down and they were about to leave Boston, an upstart agent named John Connolly arrived.

11

BOSTON, 1975

Connolly had never forgotten how Whitey had bought him an ice cream cone as a boy. And he quickly saw an opportunity for the two Southie natives to serve each other, never grasping how one-sided that relationship would become.

John Connolly had enjoyed a successful, though hardly distinguished, career in the Bureau up until that point. He’d spent his formative years as a grunt with the New York office, his tenure fairly unremarkable save for his apprehension of Frank “Cadillac” Salemme in Manhattan in 1975. To hear Connolly tell it, the tale evoked images of the Wild West, two men coming face-to-face in a desperate confrontation only one of them could survive. In reality, Connolly caught Salemme because he happened to recognize him crossing the street. The inside FBI story was that Connolly was given the information as a “setup” to get Connolly back to his home turf in Boston. And, in fact, the routine arrest won him his prized transfer to the FBI office just a few miles from where he’d been born and raised.

Coming home represented the attainment of a career goal Connolly had long pursued and he took full advantage of it. He dressed in flashy suits, had his hair professionally styled, and carried himself with a swagger and cockiness not at all in keeping with limited achievements that hardly made him the epitome of the modern-day FBI agent. Ironically, he reminded some veterans in the Boston office of a more polished version of Richie Castucci, acting “big” with not a lot to back it up.

But Connolly had a plan to change that.

Intimately acquainted with the exploits of Whitey Bulger from their common roots in Southie, the thirty-five-year-old Connolly set his sights on opening him as an informant, believing he could succeed where Paul Rico and Dennis Condon had failed. Indeed, because of his Southie ties, the young agent had legitimate street credentials—something the Bureau lacked in Boston at the time.

Bulger, though, resisted Connolly’s initial overture, held in the agent’s Plymouth overlooking Wallaston Beach, and that may have proven fortuitous for the ambitious Connolly, since there had been a change in tenor and tolerance expressed by FBIHQ. In a warning about informants, U.S. attorneys at a national conference in 1974 expressed a “belief” that the FBI had become “overly protective” of informants and made “efforts so that informants are not prosecuted so that they continue to provide intelligence information.” With both Rico and Condon taking that as their cue to leave the Bureau, the Boston office escaped recrimination and business pretty much returned to normal, only with new players, led by John Connolly, in place. History was about to repeat itself, with Whitey effectively becoming a new incarnation of Joseph Barboza, the lessons of the past not being heeded whatsoever.

Connolly’s subsequent meetings with Bulger proved much more productive precisely because Bulger saw in the ambitious agent a new means to help him achieve his own nefarious ends. Among other things, he was facing a major rift with the Angiulos, the local Italian mob family, over the lucrative placement of vending machines in various area establishments. Since Connolly’s only reason for wanting his help was to bring down those very Angiulos, Bulger saw a way to enlist the agent as an unwitting accomplice in solving his current dilemma. Bulger brought along his right-hand man Stephen “the Rifleman” Flemmi, and Connolly saw his opportunity to find the same glory achieved by Rico and Condon while avoiding the excesses that led to their ultimate downfalls at the hands of Barboza.

At the outset anyway, he was not disappointed. In 1976, Stephen Flemmi and Bulger provided information that allowed Connolly to turn a co-conspirator into a cooperating witness, identifying Joe Russo as the killer of none other than Joseph Barboza, who was gunned down in San Francisco just days after his release from prison. In a typical execution-style murder, Barboza was clipped by Russo and his gang from inside a Ford Econoline van that pulled up next to Barboza’s car and pumped him full of bullets. The van was abandoned alongside Barboza, who was left lying in a pool of blood, eerily reminiscent of victims he had left behind.

Having proven himself to his handlers, Bulger wasted no time in taking over the Winter Hill Gang in the wake of gang leader Howie Winter’s incarceration. The fact that the Italian mob remained the Bureau’s number one priority gave Bulger carte blanche to run the Irish mob however he saw fit. In fact, the more powerful he could become, the more power he could exert on the Bureau’s behalf. At least that was the thinking at the time. Connolly and his supervisor, John Morris, and Bulger and Flemmi shared one thing in common: ambition. But that was enough to drive their relationship forward and sustain it so long as each was helping to promote the success of the other.

Boston watched as the Winter Hill Gang under Bulger and Flemmi consolidated its vicious hold on the city’s rackets, thanks in large part to the federal arrests and subsequent incarceration of the competition they served up neatly on a plate. They fed names to Connolly and Morris, and the agents would take things from there. The relationship flourished, as the parties continued feeding off each other’s greed and opportunity.

But they did so at the expense of the residents of Boston, who found their lives adversely affected, even endangered, by a pair of sociopaths who had free rein to wreak havoc on the city. Whitey Bulger and Stephen Flemmi had effectively replaced Barboza and Vincent Flemmi, among others; their actions now fully facilitated by their status as FBI informants. And they also replaced Barboza as informants with the same goal in mind: receive as many free passes as needed, so long as they appeared to be furnishing good intelligence—the operative word being
appeared.

Some of that intelligence from Bulger, code named BS 1544–C-TE, helped net Joe Russo, which, in turn, netted Jimmy Charlmas, aka Ted Sharliss, for masterminding the hit on Barboza for “the Office.” When Connolly reported, though, he changed “Office” to “Outfit,” a euphemism for the New England mafia that the Boston office was still desperate to bring down. The subtle alteration was clearly designed to muddle a picture already blurred by false information. Something Connolly did quite well in his 209s, the internal vehicle for reporting informant information, whether true or not.

Connolly hit the street running on the same track as Rico and Condon, not only making the same mistakes they made, but even worse ones. Having grown up with Bulger in Boston’s Southie neighborhood, Connolly had no problem accepting a gift from the informant he also saw as his pal: that diamond ring he had emblazoned with the FBI motto: Fidelity Bravery Integrity. The ultimate irony and sadly so.

Connolly had betrayed the Bureau by going “native,” essentially choosing his Irish Boston roots over his loyalty to the organization he purported to love. There was no going back for Connolly at this point. In his determination to avoid the inglorious fates of Rico and Condon, he had assured himself a much worse one. He would later declare in court testimony, “We knew what these guys were.… All of them, top echelon informants, are murderers. The government put me in business with murderers.”

And he found a willing and able partner in fellow agent John Morris, who was promoted to supervisor and immediately got Connolly assigned to his squad. Internally, Morris was described as “imaginative, innovative and extremely industrious” with no hesitation to tackle “major projects.” They seemed perfectly matched, although Morris was as humdrum as Connolly was flashy. A family man with a receding hairline and a crumbling marriage, Morris was cut from the cloth, initially anyway, of more staid Bureau agents of the past, conservative and, you would think from appearances, by the book.