I was recently playing a live 6 handed cash game $1-2 when this spot came up. I would love your advice as to what you guys reckon even though I think I can guess your answers will be already.

Firstly, The villain is, bluntly put, the wildest maniac I have seen for a long, long time. He is essentially Sigmund Freud’s dream patient, a streak of Hunter S. Thompson and a dash of an attendee at the most recent BDSM expo. This is a rare and intriguing specimen in the game I play and the tight passive regs seem to hate this type of player. I love them and I was directly to his left. What had I done to receive such a gift? He played every single hand, I collected $90 of him in my first 3 hands and the best he showed down was 8 high. Before he made his third withdrawal at the ATM I got him all in preflop for $60. I had 8’s He had 6/4, they were suited. He casually strolled to the ATM and withdrew another $200 and bought back in. His first hand back and he bat a nit off their hand. Dinner time!

So this brings us to the hand.         

UTG: $320ish

UTG+1: $140ish

CO: $290ish

BTN: $350ish

Villain SB: $245

Hero BB: $360

Pre Flop: Hero is BB with A5

2 folds, CO raises to $6, 1 fold, SB calls, Hero raises to $13,CO calls, SB calls.

Flop: (pot $39) 8 5 5 (3 players)

SB checks, Hero bets $21, CO calls, SB calls

Turn: (pot $102) 2 (2 players)

SB checks, Hero bets $37, CO calls, SB calls.

River: (pot $213) 7 (2 players)

SB checks, Hero bets $45, CO calls, SB raises to $174 all in.

Notes on CO:

The Cut off has a relatively wide opening range in late position (standard 3x raise from him) preflop and is pretty sticky post flop if he hits or has overs to the board and the bets aren’t large. I raised to isolate the Maniac but when he called my raise and flop bet I put him on A/8, K/8 type hands or 10’s/9’s. Obviously I don’t know what Mr. Lecter in the small blind holds but I have decided to leave him out of the equation for now and focus on extracting value from CO. The reason why my turn and river bets are on the small side is for exactly this reason. From our history, I know that CO is folding to any reasonable bet but will stick around for less. He tanked my river bet and eventually decided to call.

Notes on SB:

Aside from being a maniac I picked up quite a few things on him. He will call down with 8 high on the river. When he bluffs he splashes his chips when he bets. He bluffs every time he senses weakness, which is whenever it is checked to him. I have seen him 3 bet and 4 bet on the turn which turned out to be air but I have only seen him call down on the river. I have yet to see him check shove the river with two people still to act.

When he went all in, he did it briskly but he never splashed the pot and seemed to go into his shell a bit. Alarm bells went off obviously. My thought process was that he obviously has a hand but is his hand as strong as he perceives it to be? I am getting almost 4 to 1 on a call.  

I feel like I played this hand pretty badly from the onset. Could you guys please help me with the line I should have taken and obviously if I should have made the call or not.

Thanks a bunch!