2/5, eff. stack 700ish, table very loose passive, villain is pretty loose passive, not too stationy though

Hero in CO with A9hh; 1 limper, hero makes it 20 , BTN calls, BB calls, limper calls.

Flop (80): JT6hh
Checks to hero, bets 65, V in BTN calls.

Turn(210): Kc
We pick up a gutshot to go with the flush draw.
Hero bets 125, V calls. The way he quickly calls flop and turn are suggestive to me of some kind of good draw, for the little it's worth

River (460): 5c
Hero shoves for about 500. Thoughts?

So by the river his range looks something like KQ,KJ,QJ?,AJ/hearts. I don't know if AJ calls the turn, QJ might fold as well - hard to say. If we bluff river KJ always calls, KQ might call some % of the time, and let's say the rest fold. It's definitely close - having hearts is not good and maybe AJ/QJ fold the turn. If he's on the looser side with calling wider postflop then go for it, if he's tighter then his range is very condensed - I would give up. Now if you didn't have hearts this would be a clear bluff regardless of player type.

Draw heavy board where everything misses tend to be overbluffed, also the K was a dynamic card and he still called a second street. Also if he has a draw like 98 you just check back and win, but itd be a pretty bad turn call with the K coming.

Id think his most likely range is straight (AQ, Q9 if he plays it), 2 pair (JT KJ), pair + SD (QJ KQ QT) or hearts (but there arent many combos. 8h7h? 7h6h if 6 on board isnt a heart?)

I dont think he has 66 or TT, hed raise that draw heavy of a board with that.

I think you can rep a big hand here, but youre repping a lot of bluffs too. If he can fold KQ you might have the critical mass number of combos for it to be an EV+ bluff, but even then itd be close, and I highly doubt he folds JT or better, so id probably give up.

It looks Ok

your turn bet is pretty small compared to your flop bet though

I don't like betting that big into multiple people on flop.

PRE - raise bigger over the EP limp, to drive out the BTN and the blinds. At least $25.

FLOP - just check when we're multi-way and sandwiched between the blinds and the BTN. See what everyone else does before we decide what we want to do.

We can call a single bet from the BTN if he stabs at it, but fold if any of the other V's x/r. If we c-bet, it should be less than 1/3 pot when we're multi-way, so your >3/4 pot bet size is way too big here.

TURN - if the flop checked through, we can make a delayed c-bet. AP, when the BTN calls our large c-bet next to act, I would prefer to just check-call here, rather than barrel.

RIVER - AP, just check. V called a >3/4 pot flop bet next-to-act and multi-way, and called your almost 2/3 pot turn bet. We don't want to have AXhh if we're going to bluff here.

Not a fan of flop cbet, someone hits this board almost every time and getting raised isn’t good. Bet smaller if you bet. Raise bigger pre.