Hero: CO ($500) young 20s white kid at a dream table. Majority of the table is deep and people are calling 10x raises preflop with KTo, A6o, ect and one whale in specific is never folding top pair.

V1: HJ ($400) is 30s black guy with a tough guy image. Pretty new to the table and hasn't played any hands of note. Seems loose/passive preflop but can put $ into the pot postflop. Definitely a fish and I don't expect him to make big folds.

V2: UTG ($1000) huge whale. ~100% VPIP and calling my $20 opens with A3o, A6o, A8o, ect. Won all his money with AA vs 66 vs AK on A63r flop. Can call flops with bottom pair ect. Will never fold top pair.

OTTH:

4-5 limps to hero, who raises to $17 with AT, only V1 and V2 call.

I can see an argument for limping in here, but I've been able to isolate the whale with $17-$20 raises pretty effectively and want to continue to play pots with him.

Pot $55
Flop J53
V2 checks, V1 donks $32, I just flat, V2 folds.

Normally I raise this donk bet, but just flatted to potentially keep the whale in the hand with Jx/smaller flush draw hands.

Pot $119
Turn J
V1 leads $45, Hero calls.

Pretty small sizing, but I figured typical 1/2 player just had no idea the size of the pot. Ranging him on Jx a lot here - so expected to have a lot of implied odds if I made my flush. Obviously some RIO if he just boated up, but there is also the possibility he is donking with a smaller flush draw trying to rep the J.

Pot $209
River 6
V1 bets $100, Hero??

Call or jam here. He has another ~200 behind. Obviously if we jam we value own ourselves against 55/33 but do we expect villain to 1) take this line with a smaller flush draw, and then call off our jam and 2) Still bet the river this big with Jx, and call off a shove.
His line makes a lot of sense for KJ, JQ, J9, but those combos alone don't outweigh his 55/33 combos.

If you dont expect him to make big folds then he will call with lots of jacks or diamonds, of which there are lots of combos vs the few boats. Therefore easy shove for value.

This is completely read-dependent.

If he is loose passive though he isnt donking lots of diamond combos, only with the Jd. So there is that. But shove for value is fine i think.

Based on your description of villains/table dynamics, this is a pretty easy value raise, I like it. I wouldn't confuse raising "to isolate" with what this bet accomplishes: piling money in pre when you have good pot equity.
+1
+1 my impulse is to fist-pump jam river. If he's the type to limp/call Jx pre (sounds like he is) then you're getting value from a bunch of those combos AND lower flush draws AND you can discount 55/33 because of his lead/lead/lead line.

Interesting spot...I think a lot of the river decision depends on what you believe he leads with on flop...is he leading with a AJ type of hand? or a set? I really discount a flush draw because from my experience a V will check call a flush draw against a pre flop raiser, I don't see too many typical 1/2 players taking that type of aggressive line with their draws...unless of course he had a KJ of diamonds type of hand, then he might...unfortunately I think the pre flop lead is typically 55 and 33 and then once he boats up on the turn he is betting small to "keep you in the pot"...I absolutely hate value owning myself at 1/2...so I think I lean towards a call based on the fact that he led the flop but I don't think shoving is wrong

Played well. First inclination is to jam the river ... but could that scare him off? He has $200 behind at this point, why not raise his bet to $150 and see if he calls it off or just shoves. I can't see him leading three streets with 55/33. Also, his turn bet is really weird.

OP, I like that you had a thought process behind all your decisions.

OTR I feel like V has Jx much more than 55/33 because I think he would have bomb the river with a boat. Plus most fish don't usually donk out with sets. They normally try to trap or c/r. Nor would they donk turn after filling up. They'd usually check to let the FD get there.

If we're going to raise, the choice is between min raising or shoving. Minraising could be less scary in terms of money, but it also looks more value bettish so it could make your hand look scarier and get him to hero fold.

Shoving is scarier in terms of money, but makes your hand look like a monster or made hand that you turned into a bluff.

V is a fish who doesn't make big folds and can put money into the pot...plus he has a tough guy appearance which means he's not likely to let anyone push him around. I'd consider shoving for value.

I like the raise preflop, we have the right image and the right players limping in. We really want to punish the whale's range by getting him to commit more preflop. On the flop I definitely think you could make an argument for a call or a raise. Calling is perfectly fine as long as we're willing to fold on a bricked turn, we're not really sure about V1's donk and with V2 folding I'm not really looking to be calling a turn bet. The argument for raising would be to narrow his range and knock out his bluffs with a semibluff of our own. If called though I'm looking to check/fold the turn if we miss.

As played, I certainly would fold the turn. We're not getting the odds to call and a large part of villain's range is going to be Jx and other hands that have us beat. Calling is bad here as we're not getting the proper pot odds, I understand the implied odds are there but they are cut down by the chance that we're already dead.

On river I'm really grossed out on what to do. At this point calling or shoving isn't really terrible. We really have no idea where we're at in my eyes, total way ahead way behind spot. Given lack of history with villain I'd rather just call and get to showdown and see what he was playing like this.

Results:

Bbv is that way bro =====>~~~~

Villain's flop and turn actions make sense if you think he puts you on AK, then decides to represent a jack on the turn.

Just read the results but I'm jamming every time here. I try not to worry about boats until I am sufficiently deeper where bet/folding or jamming into a boat would be a travesty.

Raise the flop to $115. Gives you more options on the turn and if he ships it on the flop that's fine too. I'd probably shove river if V is the type that won't fold Jx.

I already said I wasn't really worried about the actual results, was more interested in seeing if people agreed that a shove is profitable in that spot (which I still think it is).

This is the normal line I would take - but I thought there was more value in letting the whale continue if he flopped any equity/dominated draws. He would continue with any hand as weak as a naked gutshot on the flop and would pay off very light on later streets even on 3-flush boards.

I want to zoom in on that turn bet.

Villain bets $45 into $119. Is that a pot control type of bet? Does that bet scream out "I'm protecting my hand"? It almost feels like he's betting so you don't (or that if you raise he's out of there).

I see bets like this all the time. Sometimes I even make them myself to try and control the action. Any opinions on that turn bet?

Seems like a great reason to raise

I don't expect him to continue nearly as wide in the face of a $100+ raise.

I figured by calling, I miss out on the fold equity I generate by raising, but if it often brings along the whale with weak hands, it would give me more than enough direct/implied odds to draw to my flush.

Yeah I'm really curious what sizing he would have used/if he would have bet on the turn with a J, boat, and flush draw.

Obviously in hindsight a turn raise would have worked, but I figured that it would be really hard for villain to lead into me again without a Jack and didn't think I had any fold equity on the turn at all.

If he made his hand on the turn? Probably $100. That was his river bet when he made his hand.

Your decision not to raise that turn bet probably had a lot to do with you not having your flush yet. In the moment you probably thought about the effective odds of stacking him if you hit your flush for a $45 call. No-brainer.

I dunno, like I said I see raises for 1/4, 1/3 of the pot all the time at 1/2. It's either pot control or the idiot just doesn't think about the pot when he bets and is just trying to put something out there that matches the strength of his hand. I have NO IDEA what V1 in this hand was thinking ...

It is sometimes what you described and sometimes a strong hand thinking that is the most he can get you to call when you have few or no outs.