I am UTG+1 with a stack of $475. I'm dealt two black kings (K K). I open for $10 and have three callers, including the big blind. Flop is 4 5 8. The big blind checks. I bet $25 into a $40 pot and the low jack calls. The big blind, a loose aggressive player, raises to $110. All 3 of us in the hand have similar stack sizes. After pondering between a call and a shove, I decide to shove with my remaining stack. The low jack folds and the big blind calls. The big blind has 6 and 9... a flush draw and a gut shot (so, I'm 57% to 43% post flop).

I can't decide whether I should have called his $110 bet rather than shoved. I did not think the big blind had a pocket pair because he would likely 3-bet (based on prior experience playing with him), so his range likely included a flush or straight draw... or he possibly flopped the straight. I also wanted to isolate and get the low jack, another LAG, out of the hand.

Turn is 4 and river 10, so he hits his flush draw.

I would like some advice on whether I should have played this hand differently. Thank you.

You were able to go AI when you were a favorite. That's a good thing, unless you're playing with scared money.

Congrats on the well-played hand and on this initial post...after lurking for 5 years!?

Preflop raise size? How many people do you expect to call?

Why not flat the flop and play a turn in position?

He really threebets pre with 44/55?

It depends how loose aggressive he really is but I typically just fold flop in these spots. People who checkraise vs two players on a board like this generally aren't kidding. If you give him { 55-44,76s,54s,AcJc,AcTc,Ac9c,Ac7c,Tc7c,9c7c,Ac6c,9c6c ,Ac4c,7c4c,6c4c,Ac3c,4c3c,Ac2c } (basically any nut flush draw, any combo draw, 76s, plausible sets/two pairs) you have like 34% equity. But if the BB is super aggressive and checkraises like this are the norm for him, then I'd flat and put pressure on him on safe turns. That's if he's the type to checkraise with dubious hands like 56 or T9cc.

Thanks Chris. He really does 3-bet light often... and I've seen him do it with small pocket pairs pre-flop. I think my equity was more than 34% against his range, but less than my real time analysis at the table. In hindsight, I made a mistake not flatting his post-flop bet. As you note, a flat would allow me to apply pressure on safe turns... and, with a club or another straight card on the turn, I could have gotten away from the hand. Moreover, in this case, a safe card did come on the turn... and I could have made a good sized bet and taken down the pot. Drat.