Fifth street is such a complex beast that you should have a super read on your opponent before trying something funky on the river. So for the most part if you’re check-raise bluffing or bluff-raising on the river you need to ask yourself if you’re suffering from fancy play syndrome. That does not mean it is always bad, but you should have good reasons for making such a volatile move and that means using logical thought rather than just shoving and hoping.
Good players to check-raise bluff are reasonable grinders who are often weak-tight and lack the fortitude to trust their reads and would rather pick easier spots than gifting someone a big pot with top pair. You should always think two things before trying these high-octane moves on the river, “Will that player be able to read this play as I’m trying to tell it?” and “Will they be able to lay their hand down?” If you come up with two positive answers, it is usually fine to go ahead and pull the trigger. Players often feel you are pulling moves on them but lack the heart and courage of conviction to follow through with these reads. Bad players to check-raise bluff are idiotic fish and very good thinking players, instead pick on the good but not great players that can pass hands on dangerous boards.
Story telling
If you do elect to check-raise bluff a player, make sure your story actually makes sense. Let’s say you have KhQh on a Jc-Ts-7s board, you bet against a very good player when you are both 200 big blinds deep. Your opponent calls. The turn is a 4d. You bet and they call again. The river is a 4s and you check-raise the river now, making a large raise over their half pot bet. These are the sort of spots where, provided your opponent is a solid thinking player, he will be forced to fold a lot of the time. Make sure that your opponent is capable of folding a flush and your image is clean enough to represent that you have a monster hand. If your opponent thinks that you are a crazy player this is not necessarily the time to pull a move; your opponent has shown a lot of strength calling you down and then betting the river. Pulling these moves requires great hand-reading ability and understanding of your opponent.
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