This team needs a shake up as some have mentioned. Also, as the more astutue people have mentioned Gillis still seems to be fulfilling a role as player GM to players that aren't his contractables.
I get the idea in real life as the contracts portray to hapiness but's it detrimental to the team.
I can't see us acheiving success until he's gone because he's stubborn and his law degree also makes it obvious that chasing success would be detrimental to his chances at not blowing this job.
He has no incentive to make this team better, he's selling out, the team is moderately wining, and he tied his own hands.
Get rid of him. He will be beter once he learns this lesson.