Bulger isn't just working the FBI—he's also working the Mafia. By playing both sides against each other—all while under the personal protection of Connolly—Bulger is able to build an insane criminal empire without breaking a sweat.

Although John Morris is specifically chosen to be the supervisor of the Organized Crime Squad due to his fastidious devotion to the rules, it doesn't take much for that devotion to fall by the wayside. After all, Connolly is breaking all the rules, and he seems to be getting along just fine. Why shouldn't Morris get in on the action?