Whitey Bulger on trial: what last-minute legal maneuvers portend

James 'Whitey' Bulger, reputed Boston organized-crime boss and former FBI Most Wanted fugitive, appeared in federal court Monday. Some of the trial's likely narratives were evident in pretrial motions.

It’s been a long time coming, thanks to a manhunt that took 16 years, but the trial of James “Whitey” Bulger is about to begin.

Mr. Bulger, long at the top of the FBI’s Most Wanted list, sat before a US District Court judge Monday for a pretrial hearing, dressed in an orange jumpsuit with a long-sleeved white shirt underneath.

He is alleged to have maintained a lucrative crime racket in South Boston through a quarter-century reign of terror ending in the mid-1990s. Federal prosecutors are charging him with 19 murders, extortion, money laundering, and other crimes.

The 83-year-old Bulger showed little expression Monday, staring forward with his arms folded in front of him for much of the hearing. He wore eyeglasses and, unlike when he was captured at a California apartment in 2011, the defendant was clean-shaven.

But the case is packed with emotion. Victims’ families are eager for justice. For residents of the region, the trial embodies a years-long effort to root out entrenched organized crime.

The trial also dredges up boatloads of controversy for the FBI, which for years partnered with Bulger as a “top echelon” informant in its battle against the Mafia – a relationship that went sour as the FBI handler devolved into aiding Bulger.

“The FBI is on trial along with Whitey,” says Dick Lehr, who teaches journalism at Boston University and is the author of several books on Bulger.

Bulger’s former handler has already been convicted of crimes tied to the affair, but the Bulger trial could bring out new details about flawed behavior within the bureau’s Boston office.

And Bulger himself isn’t going to remain silent and on the sidelines.

Instead, he’s expected to take the witness stand, even as some of his former associates testify against him. According to recent reports in The Boston Globe, Bulger hopes to refute both the “informant” label and the charge that he killed two women.

The trial could last through the summer, with dozens of witnesses on each side. It will put a national spotlight on a man who grew up in Irish-American South Boston, did time in prisons including Alcatraz, and then rose to become a feared presence in New England’s largest city.

On Monday, some of the trial’s likely narratives were evident in pretrial motions being weighed by Judge Denise Casper.

The defense will seek to cast doubt on various prosecution witnesses, on the basis of their background as criminals-turned-informants or, in the case of FBI supervisor John Morris, having cut immunity deals.

Federal prosecutors will seek to prove Bulger’s guilt, and they hope to build their case in part by portraying his relationship with the FBI since the 1970s.

Prosecuting attorney Fred Wyshak told Judge Casper Monday that FBI agent John Connolly (who handled Bulger as an informant) accepted payment from Bulger and was engaged in a “symbiotic relationship” from which both sides benefited.

Mr. Wyshak said the FBI agent gained stature by gathering information from Bulger and his associate, Stephen “the Rifleman” Flemmi, that helped to dismantle Boston’s arm of La Cosa Nostra.

Bulger gained, too, Wyshak said, rising to the “top of the [criminal] food chain” in the area, thanks to his protected status and information passed to him by the FBI.

Many legal experts expect some form of guilty verdict. But with a courtroom drama that draws together Bulger and his former partners, victims’ families, and law enforcement into the same relatively small room, the trial could feel like a roller-coaster ride all the same.

Jury selection alone could take most of this week, in a bid to find locals who aren’t already so steeped in the story that their impartiality is in doubt.