I wouldn't have raised here. "Finding out where you're at" is a very power thing, but in this situation, I don't think it would have done him any good. He was first to act, so if he bets out, and is raised, he'll probably still call w/ TPgK ... I would. If he check-raises, and both players flat call, he's not in too much better shape b/c now he's gotta lead out on the flop.
What information did he gain by raising?
Oh, and being first to act would probably make it hard to do a free card play. Checking from first position on the turn after check-raising the flop is a huge sign of weakness. If his opponents had any wherewithall, they would bet into him to "see where they were at."
__________________
|