Both, it could be argued, were felled by a certain hubris -- Whitey in thinking he could play the FBI against itself for personal gain, and Billy in holding political grudges too long. To the end, he hoped he could wall off his relationship with his brother from public scrutiny.
"Both of them were sort of hounded into submission – they had to flee their chosen fields, hounded out," said Dan Payne, a veteran Democratic consultant based on Boston. "They got to the top, and they went too far. They got too radioactive."
Paths Diverged Early
The Bulgers' paths had diverged by the time the family left Dorchester for south Boston, in the late 1930s, when Billy was four. Billy was a terrific student, a "Triple Eagle," to locals – a graduate of Boston College High School who went on to earn his undergraduate and law degrees at BC as well.
Whitey took to the rough-and-tumble streets. He was still in his 20s at the time of his first federal conviction, for bank robbery, in 1956. Whitey was serving his sentence at Alcatraz when his younger brother won his first elected office, to the Massachusetts House of Representatives, in 1960.
Back home in Southie by the mid-1960s, Whitey rose through the ranks of the Winter Hill gang, the Somerville-based Irish mob that came to dominate the region's underworld. To the extent that he was known in the 1970s and 1980s, he was something of a neighborhood Robin Hood, known by locals for keeping order in the neighborhood and keeping drugs out.
He would secretly become an FBI informant. Subsequent federal investigations would reveal the extent to which he used those connections to end the careers, and often the lives, of would-be rivals.
Billy, meanwhile, became a State House kingpin. He won a seat in the state Senate in 1970, and rose from a back bench to take over the Senate presidency in 1978.
He wouldn't relinquish that post for a record 18 years, until a one-time rival – Republican Gov. Bill Weld – found him a sinecure as president of UMass.
Billy Bulger used a mix of ruthlessness and charm to wield power and snuff out rivals like few who've come before or since. He once famously wiped out the budget of a local housing court judge who didn't deliver a promised job for an ally.
Even fierce rivals had to sit through his biting roasts at the annual breakfast he hosted on St. Patrick's Day weekend. After then Gov. Michael Dukakis caved to another Bulger demand, while Dukakis was running for president in 1988, one pol grumbled to a reporter, "How's he going to stand up to the Russians when he can't stand up to the corrupt midget?"
Bulger had close brushes with authorities – he narrowly avoided indictment in a development scheme that unraveled in 1990 – but rivals went down in federal probes even as his career flourished. His colorful memoir, "While the Music Lasts: My Life in Politics," appeared the year after his brother disappeared, tipped off by an FBI agent that federal agents were moving in.
To many friends and enemies alike, the lasting image of Billy Bulger came at the last St. Patrick's Day breakfast in South Boston while he was at his pinnacle, in 2003. Sen. John Kerry looked over at Bulger, and then over at the newly elected governor, Mitt Romney, who'd announced plans to blow up the UMass system – and thus Bulger's job.
"My money's on Bulger," he said.
The crowd roared, and even Romney had to smile.
But three months later, Bulger was testifying before Congress at last about his brother. Five months later, he was ousted from his job, forced into retirement before his time.
Whitey would remain free for another remarkable eight years. His legend only grew, enhanced by Jack Nicholson and the grainy photos that occasionally purported to depict a master of deception.
In the end, Whitey Bulger was found hiding almost in plain sight, far from Southie, in Santa Monica, Calif.
"It's amazing they were able to keep their lives so segregated, so compartmentalized," Payne said. "Their spheres of influence never crossed. That's what made their stories so exotic."