First time posting, had to manually type the hand because I have no idea how to export hands from the site I play at, so please point out if you spot any mistakes.

BU: 103.4 bb
Hero (SB): 100 bb
BB: 289.1 bb
UTG: 104.8 bb
MP: 36.1 bb
CO: 120.7 bb

Pre Flop: (1.5 bb) Hero is SB with KK
1 fold, MP raises to 2 bb, CO calls 2 bb, 1 fold, Hero raises to 10 bb, BB calls 9 bb, MP calls 8 bb, CO call 8 bb.

Flop: (40 bb) K74 (4 players)
Hero bets 24.8 bb, BB folds, MP raises to 26.1 bb all in, CO raises to 110.7 bb all in, Hero calls 65.2 bb all in.

CO is an aggresive whale, saw him donk and shove 68bb vs raise with 65o OESD, and raise flop multiway with 52s bottom pair. MP is unknown but assumed fish because of stack, and BB is a TAG fish.

I was considering whether a check or a bet would be better here. I decided to bet targeting the hands that would be willing to pay me (mainly weaker sets and draws, or even slowplayed AA) in order to jam OTT. With an SPR of 2.38 (ignoring the shortstack), I think a lower sizing would have been better, somewhere around 60% pot so draws would lean more towards calling, and would feel pot committed by the turn where I have an 80% pot shove supposing only one of them calls.

A check raise was also tempting at the moment, would also work against draws and sets and might get some money from lower PP, but I was scared of the (I now think unlikely) scenario where everyone behind me checks and I lose value from draws / get outdrawn / scary card hits and cannot extract value from worse strong hands.

wp

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I'd bet 13bbs so the action is reopened if the short stack decides to shove and the cutoff decides to flat. Definitely betting though.

That was the scenario I was hoping for if I decided to bet smaller, but while playing the hand I reached the conclusion that targetting the part of his (any of them) range that calls a decently sized flop bet and a turn jam was for the best. Was that mindset too greedy and against a range too narrow?

As described, the whale is likely going to raise any draw or decent made hand, so you don't really need to target the top of his range (he will get that in for you). So the smaller bet size really just gives an additional villain (MP) the opportunity to reopen the action for you. It might also cause the whale to spazz with with air.

Worst case is that the whale flats and the other two fold - and even then it will be pretty easy to play going forward. The pot will be 66bb and you have and SPR of around 1 and should be able to get it in by the river, particularly as you can pretty confidently put it in against the whale on a flush board after a flat (he seems almost certain to semibluff any flush draw on the flop).

Standard you have the nuts lol? The fact these dudes are short and spewing in your face vaildates your play.

Yeah I like the idea of a small bet against our short stacked whale. Seems like the most EV play. Other than that only change I could make would be to 3bet a little more preflop maybe 11.5BB with both of these fish calling us and were OOP.

Whale was full stack and the short was unknown, but I get what you mean.