In point of fact, that overconfidence is rapidly becoming a lack of confidence. Neither of them has lost many pieces, Obi-Wan continues to stock himself, and at this point the only way out of the deadlock would be to surrender pieces. He's kept his line of pawns relatively intact, and behind them is a full line of pieces surrounding his king.

Obi-Wan hasn't set a trap. He's set a stalemate. One Wesley has to break by force if he hopes to eliminate it.

And that brings Wesley's play to a halt as he considers it.

"Well, the law firm was evil. In the literal and supernatural sense. Losing my position there would be a step up."

Wesley decides it'd be better to not mention the dying part if he doesn't have to. Or the fact that dying won't actually release him from the contracts Wolfram and Hart has over him. Just make the joke and move on.

Move on to this stalemate. He can take pawns, but whatever he uses will be sacrificed- and trading for pawns would be a losing proposition.

He'd have to set up a winning rally. So when he finally begins moving again, his movements are no longer aggressive. He begins spreading his pieces out, keeping only a scarce few pieces in advance to capitalize if his opponent tried to advance again.

"The cost of a moral victory, I suppose."