I have a theory. Let me melt the steel beams in your brains:
Connor hates being an Oiler. Hated it since it was announced that they got the 1st overall pick. You can tell by his reaction during the lottery.
He didn't wanna pull an Eric Lindros, so he sucks it up. It also doesn't help that Messier was assigned to guard him, in case he escapes. Connor actually has to answer and respond to Mess' calls and texts, or else Connor's family gets shipped off to the Oil Sands as slaves. The Connor/Mess commercials are more sinister than you think.
Connor, deciding that killing his career was the only way to escape the Oilers' tight grip on his life, hires Manning and Del Zotto via a series of connections, to intentionally run him into the boards in hopes of an injury.
Connor might disappear and assume a new identity now that he might be free.