If he wins both, I'd seriously consider bringing him back. It shows he can compete with the best.
Moot though, he has never proved in his entire career he can do something like that.
Your second line is exactly why I wouldn't consider bringing him back even if he wins out.
Also, until you consistently beat the worst, "competing" with the best is meaningless.
Jim is, was, and will always be in over his head in this league.