The effort to score the $2 million most-wanted bounty kicked off in the late summer of 2010 when retired Montreal police officers John Westlake and Andre Savard decided over breakfast to see if the long-sought criminal might be living under-the-radar in Montreal.
Montreal, with a large pool of possibly sympathetic allies and a francophone population less-aware of American criminals, seemed like a logical place for such a fugitive to hide.
As well, Bulger's son-in-law Chris Nilan played for the Montreal Canadiens for many years and Bulger's onetime FBI contact John Connolly reported that Bulger had previously visited Montreal, where he felt comfortable.
The two retired officers, along with four others they recruited, spent many hours staking known meeting places of Irish hoods.
"We didn't ask people. Do that and you're burned. They wouldn't turn him in. One, they're not rats and two, they might get killed for doing it," said Westlake.
The effort consisted of watching people come in and out of homes, bars and other places where West End criminals were known to assemble.
The group wasn't even keen on tipping off the FBI, for fear the Americans might scoop Bulger up in Montreal and leave them without their reward.
"We called the FBI to tell them what we were doing. They wanted to come up and see us to show them what we had," said Westlake. "We said we'll call you when we get him."
The team spent a couple of days a week scoping out locations but the time devoted was enough to create a small obsession.
"One warm day I saw a guy sitting on a bench smoking a cigarette on Terrebonne near Cavendish and I had Bulger on my mind so much that I thought it was him," said Westlake.
The effort ended on June 22, 2011 when Bulger was discovered living in Santa Monica, California.