[W. Deranged]

There are several reasons this river bluff raise is really -EV:

1. Look at the board texture. The turn and river came undercard to a T. Villain has very little reason to believe his T is not good. If he was check-raising with a flush draw, it hit, and he's certainly not folding a flush draw.

2. You haven't really represented enough of a hand to make villain afraid. Most monster hands would have either three-bet the flop or raised the turn. Waiting to raise the river doesn't make much sense here with a hand like AA or ever TT. Only 88 would be a logical hand to raise the river with. Even though most donkish opponents don't read hands nearly that well, they do have some sense for these types of things.

3. You picked the totally wrong opponent. A 42/2/.8 is a passive fish. Fish don't like to check-raise the flop with hands they have any intent to lay down at any point. They also in general don't fold the river for one bet.

4. The pot is too big. Though it makes the bluff more valuable when it works, I think the pot is effectively big enough that like 60% of opponents at 2/4 are simply NEVER folding anything because the pot's too big.

I think this bluff is like a 1.8 BB mistake.