In October of 1993, a young liberal senator of the Massachusetts General Court launched a campaign to dethrone the chamber’s president, who had first been elected to the office in 1978. It was time, said Norfolk upstart William Keating, to clear the air in the statehouse. The old guard, Keating claimed, was rotten and out of touch; a new generation was ready—and entitled—to take the reins from the last survivors of Boston’s bygone era of machine politicians.

Billy Bulger was his white whale. A South Boston native, the Senate president had first been elected to the General Court in 1960. Inconveniently for Keating, Bulger was famously resistant to the kind of corruption and underhanded dealing that most people objected to in old-school city politics. But he was a savvy politician, and he ran a tight ship in the Senate. What’s more, he was a socially conservative populist in the old Boston Democrat mode; his challenger sat in the center on markets and firmly to the left on social issues. There was little room for Bill Keating to move upward in a Senate still led by Billy Bulger. It didn’t help that Bulger thought very little of Keating’s mental abilities, and didn’t do very much to hide the fact.