I'm guessing the cost of actually doing this is more than he has. And even if he wins, I'm sure King.com will spend months or years trying to appeal the ruling which will cost him more money.

Well if the case is strong enough, the US at least you don't need money, you tell the lawyers they can keep the the money all you want is to establish your right to the trademark.

Then they go off and bring this guy down, make their money, and you get the satisfaction of knowing that your trademark is safe.

...unless the law is clear, and he's destined to lose. Then no lawyer will touch it on the terms you describe.

...is this the kind of battle the EFF fights?