Late on day 2 of the main event. 3 tables remain. We are 7 handed. Average stack just under 1M. No one at our table is super short. I think the smallest stack is 350k.
I am the most inexperienced player at the table; my stack is just over 1M. I have been playing tighter than everyone else because I thought I was at a disadvantage post flop against many of the other players, as I felt my plays were straightforward and readable.

On this hand opponent is directly to my left. Loose Aggressive, stack ~850k. He had been directly to my right on our previous table, and our positions were switched after the redraw to 3 tables. He had been opening and 3 betting liberally the whole time I played with him, and continuing with aggression post flop. His reads were often good, and he was very tough to play against, especially for me and my (in)experience. Even in position, I didn't enjoy playing pots with him.

Enough setup, here's the action:

Blinds 4000/10000/20000

Folds to MP to my right, who opens for 50k, which had been his standard open. He had been opening 1+ hand per orbit when folded to him.
I'm in CO with 88. I think I should always be playing this hand, and I probably should be 3 betting it, given my image at the table. In hindsight, a 3 bet to ~150k probably wins me the pot preflop, but hindsight is 20/20, and I don't want to be results oriented in my analysis.

So most likely 3bet > flat > fold

Anyways, I just flat the 50k, hoping to see a good flop for my pair, but of course main opponent on the Button 3-bets to 200k. both blinds fold, initial raiser folds, action to me. I felt like this was a pretty textbook squeeze raise from the button, and a perfect spot for him in position on both players with 50k committed. His range here includes any pair, connected cards, Broadway combos, and any ace, as well as the possibility of some total bluff 3bet/fold type of hands.I thought about shoving over top, but I would've hated myself if opponent actually woke up with a bigger pair and busted me in this spot. I just couldn't pull the trigger on 1M chips in this spot, knowing that my initial flat removes big pairs and AK-AQ from my range. Thinking back, a 4bet to 500k is probably a decent play here, as it folds out a number of hands, and if I get 5bet shoved on I actually have a chance to lay down my middle pair and still have playability with 500k chips. Folding here i think is nitty as hell, but I'd been playing tight anyways, so I can make a case for folding and looking for a better spot later. After all, I should be in no hurry here with an above average stack when the pay jumps are starting to increase incrementally every 2 or 3 players that get eliminated.

So most likely 4 bet > fold > call

So I probably make the worst play possible out of position and call the 3 bet.

Flop comes 345, and IIRC I think there were 2 clubs. Not a bad flop for my hand, though, I don't think. I check and opponent bets ~100k.
Seemed smallish for a continuation bet, and the flop was all under cards to my pair, so I thought this would be a good spot for a check raise. At least I would find out where I was. I made it 250k, and opponent takes around 30 seconds to think silently and makes the call.

Turn is a 2. Board reads 2345. I felt like I was in a **** spot here, as I knew there was no way I could get to showdown without committing more chips against this player. If I check, I think he pushes his entire range here and puts me in an awkward spot. On this board my hand is just a bluff now, as every pair 22-66 has me destroyed. Any ace or 6 makes the straight, and many of those are in opponent's range as well, especially if they're clubs. 77 is the only thing I'm actually beating. I couldn't shake the thought that there was a chance that opponent floated my check raise with over cards, planning on shoving scare cards on the turn or possibly hitting a pair which was good. I thought there was a decent chance that he had an over pair that I could get him to fold, but now that I think about it, he would've bet more on the flop with an over pair. Anyhow, I took the aggressive line and pushed all in.

I'd like to hear some feedback on this one. I think I have a good idea how I could've played it better, but it's taken me 2 days to think it through. Amazes me that some can process this amount of info in the time it takes to play a poker hand, but I hope to improve enough to be able to do it some day!

Cheers!

I'm 3 betting pre here. Could also 4 bet/fold as played. Not liking your jam as played

I don't like my jam here, either. I was hoping to get some outside input on what else to do. Check/fold? At the time, I thought that betting it was the only way I could win the pot, and for some reason in that moment I couldn't just let the hand go with a check and a fold.
Opponent's call of my flop check raise should have sent alarm bells of strength off in my head, but I just kept thinking that I was being bullied and needed to finally do something about it.

There were three big problems in this hand:

1. When the button 3-bets pre, our options really need to be to 4-bet jam or fold. If you think the button is squeezing wide as you suggest, then a 4-bet jam makes some sense, as we should see plenty of folds and if we get called we should have 33%-ish equity vs. our opponents' likely calling range. I don't think folding pre is outrageous, though, albeit a little tight, as for the button squeezing range over an MP open shouldn't be that wide. Calling seems to be the worst option simply because we create a small SPR (stack to pot ratio) and we have a hand that generally doesn't flop well.

2. On the flop, when we get c-bet (and it's a tiny c-bet), I think our best option is to shove. Our opponent has about 550K behind into a pot that's ~600K. While we are dead to rights vs. overpairs, if our opponent is shoving as wide as you think he is, he'll have plenty of random overcard combos that we can get to fold. Those hands are almost certainly not folding when they have to call 150K more into a pot of 1M - they'll be getting almost the direct price to continue with hands as weak as Ax. If we're not shoving, I'd much prefer calling, because at least there is some reasonable chance our opponent might shut down on the turn after we call the c-bet.

3. On the turn, as played, we have to check/fold this turn. Even if our opponent decided to float with some random Ax hand that hand just got there. It sucks that we got that far and have to fold, but that 2 is literally one of the worst cards in the deck for us as the only hands we might have gotten to fold to a shove are never folding now.

I think I would 3b with reads, if im readless or OR is a nit don't mind a flat.

I dont think I would fold or flat to aggro squeezer

Thank you for your analysis. I agree with pretty much everything you said here.

This was my first live tournament, and once we got down to 4 and then 3 tables, it seemed obvious to me that I was the most inexperienced player at the table. I felt like I played really well up until this one hand, and it just overloaded my nerves and my brain shut down. One bad move is all it takes to ruin 2 day's worth of great card playing, so I'm happy to learn that lesson in my first event!

I think you are correct in these assessments.

With my image, a 3 bet of OR probably would have taken down the pot preflop. I can't imagine that the guy behind me would continue in this scenario, facing a 3 bet to ~150k. If he does, he still stacks me, but I doubt I would feel like I played the hand as poorly as I did. OR folded to an aggro 3 bet, so he certainly would have folded to my 3 bet as well.

As for the second half, I'll just have to gain some experience in order to feel more comfortable shipping my whole stack in situations like this late in an event when I feel like I have a good read, and be ok with it the times that I'm wrong.

I know it's results oriented, but looking back, if I shove over the 3bet, opponent folds and I pick up a pot equal to 20% of my stack, which is a healthy win at this point in the event!

Agree with jpgiro, but wanted to say how horrendous an idea 4bet/folding pre would be. You mentioned making it 500k, then folding. You would be folding instead of calling 350k more to win 1.4M. You literally would have to call if he inadvertently showed you AA.

Flatting or 3b the first time are both fine. Folding, jamming or flatting the 200k all have merits, but 4b/fold is atrociously bad.

Calling or CRAI flop are both fine.

Turn is just a check/fold.

Great concise feedback. +1

I would have 3 bet pre, if I had called, I would have jammed on the squeezer pre (all in). As played it's a check/fold on turn.

I'm jamming to that button 3b pre. It is one of those crappy spots where you just don't want to play post oop, but when you 4b shove, your hand looks like exactly what it is. That said, most will still fold broadway hands that you flip against for their tourney life (outside of AK and AQ) and you are rarely crushed. It's just too juicy a spot for him to squeeze--we have to put him to the test here.

i completely agree with blackaces, if we are not gonna check raise allin with this kind of board why are we calling pre?

agree with above sentiments that CRAI otf is our best option as played and 4b jamming to aggro squeezer seems optimal