Why couldn't he go?
He was the most qualified person for the job, the only reason any of this was even happening was because he had understood the true purpose of the gate.
He deserved this more than anyone.

They needed him there, in Atlantis.
He knew more about the Ancients than anyone, he knew the language fluently, and that was the city of the Ancients!
But Jack wouldn't let him go, never saying why.
And so it gnawed at the edges of his mind, always there, a sick feeling in the pit of his stomach.

Envy.