This is a hand from late in a session Friday night. I won't say anything else about it now so I don't bias the comments.

SETUP

Hero (UTG+1) - Overall, my image is very TAG, bordering on nitty. Some of the folks have started to make comments about getting out of my way when I get involved in a hand. I'm up a little over $300 for the session, total stack size of $500+.

Villain (BTN) - The villain in this hand is a young player who has been here for a little while now. He started down, but has since built up a nice stack. He's probably got $400, maybe a little more. I've seen him make a few moves. He 3-bet me all in with a player in between for ~$50 with 44 early on, for example. He seems aggressive but not crazy. He tries to see a good number of flops.

PREFLOP:

Hero is dealt KK.

1 limper, hero raises to $16. 2 players behind (including Villain), plus one of the blinds and the original limper call. 5 players to the flop.

Comments: Pretty standard here. I got more callers than I would have expected, but nothing out of the ordinary.

FLOP:

Pot is ~$75
Flop comes 533, two-suited.

Checked, Hero bets $45, Villain raises to $100, everyone else folds. Hero thinks about it and calls.

Comments: I thought I was in a way-ahead way-behind situation here, and this didn't seem like the kind of place to commit my stack. I thought I was ahead enough to call (he could easily have a smaller PP), but I didn't like the situation.

TURN:

Pot is ~$275.
Turn is another 3. Board is now 5-3-3-3, two-suited.

Hero thinks briefly, then checks. Villain does the same.

Comments: Well, my hand improved, sort of. I don't have to worry about the flush draw, but otherwise things haven't really changed. I didn't want to bloat the pot any more while OOP. His turn check kind of surprised me, though.

RIVER:

Pot is still ~$275.
Turn is an A, completing the flush draw. Board is now A-5-3-3-3, with three of a suit. I didn't have the K blocker.

Hero insta-checks (not sure why I didn't think this through longer). Villain thinks briefly, then bets. I think it was $125, but it may have been $150. Hero thinks for a while and...???

Comments: His bet put me in a really tough position on this one and I went back and forth a bit. I'll let the rest of you debate the merits of what to do, then I'll tell you what actually happened.

AP river is an easy call.

V as described will bet this A with nearly 100% of his holdings, so if we check, we should call!

I like the check as I think it is a higher profit play from an aggressive V than a blocker bet. The blocker bet loses more if he is aggressive enough to bluff raise it (since we always fold) and doesnt win as much from his worse hands that just call or fold and don't let him bluff.

Obviously he can have an A here since he checked behind on the turn which was surprising, but how often does he have worse than Aces full of fives? A LOT of the time IMO.

This spot would come down to feel/reads for me some of the time (most of the time I'm calling anyway due to the strength of my hand). Do I think V was calling pre and raising flop with a worse PP or with a bluffing A or with a 5?
If he is calling and betting with worse PP's and not with pure bluffs, then this is an easy call. If he is bluffing with Ax a lot then I fold (less than 10% of the time).

My read is he has quads and you called.

Yea I'm folding here.

So Villain min raised ur "not too small" cbet on this board with 4 other players left behind?
I never put people on quads, but this is one of them...his turn check actually is kinda confusing, ur hand is face-up now, and he knows u r not easily folding a FH, but since he is tricky, it could make sense for him to slowplay here....worst u will see here is fives full imo....
A min raise in a 5way flop is toooo strong...I think I fold the flop

I dont think he'll just minraise with A5s with 4 other players left to act...agree with everything else

I donk lead the turn for like 1/4 pot and make him either make a terrible float or raise me because he literally can't fold anything cause it'll destroy him. Trust me, it works against young guys w/ big egos A LOT. I really want to fold river. I think he has A here a lot... not fully decided, tough spot.

I'm calling river. V could have any other PP and might think 1010/JJ is good or try to rep an A or 3.

Do 1/2 players ever turn 66-TT into a bluff here otr? Especially after shutting down ott? Doesn't anyone else think b/f >>> c/c? Don't mind the flop or turn play.

Stacks and the pot otr are about the same, 275-285. Betting 1/2 pot and getting shoved is a disgusting spot, we're never really ahead but if we are just 16ish% of the time it's a mandatory call.

I'd put in a blocker bet. It's more of a tournament scenario, there's a medium amount to bet where villain can't know if we're committed or not. I think it's 1/4-1/3 of remaining stack, I remember watching a video of a $200 rebuy on Ladsbroke. So villain has to be confused by our bet and shoving whether he's bluffing or nutted makes him unsure on both sides. I b/f about 80.

I would just raise flop to $210 and shove turn.
Theres alot of hands villian would raise the flop that we are ahead of, and we can also rep alot of overcards+fd that villian's overpairs may call vs our raise.
Plus the villian is a non-nit, so his raising range would be wider.
Flatting raises oop when we have a strong, but vulnerable hand, sucks.

That check on the turn was horrendous

So on the flop villain raises to 100 which is 1/4 of his stack and then checks back the turn in position. Sounds to me like an A high (maybe A high flush draw or A5) trying to buy the pot on the flop who then made the bingo card on the river which didn't cost him anything more. Now he bets 1/2 his remaining stack. Just fold here and kick yourself a little for not betting the turn.

bet turn

as played blocking bet/fold river. check calling is not an option.

Grunch

I think you made the same mistake that a lot of people make in these cooler-type threads. When your first suspicion arose that you might be beat instead of taking the line that gets you maximum value when you're not beat (which is most of the time) you got passive and minimized your value in a hopeless attempt to minimize your loss when you're behind.

When villain raises the flop there is no longer any way we can fold our hand. Once villain makes it $100 the pot will be $275 once we call and effective stacks will be $284. Now what if a 7 comes off ott and he shoves, are we folding? When he shoved the 44 hand he showed that he values low pps and tends to put his opponents on high cards so against us he could have 88-QQ when he raises this flop (he could have a hand as good as QQ b/c you have a tight image and he may be afraid to 3bet when you open for 8x)

So here is my shot at a range for villain when he raises flop:

Board: 5h 3h 3s

Hand 0: 79.080% { KK }
Hand 1: 20.920% { QQ-88, 55, 33, AhQh, AhJh, 7h6h }

Notes:
1. I only put his very best big draws in there b/c the board is paired and we don't know him well enough to assume he raises his big draws often. All we know is he shipped $50 w/44 against 2 players so he's not playing too scared.
2. A decent amount of the time he slowplays his 55 or 33 and he just flats his 88-QQ but I didn't eliminate any combos to weigh his range b/c I figure it cancels out

Reasons to raise flop:
1. To get value from 88-QQ before a card higher than his pair hits and kills our action
2. To charge his big flush draws should he choose to call our raise
3. We are oop so we have to establish the betting lead to ensure we get the rest of the money in ott
3. If he has 55 or 33 to beat us there is no way we can fold so we need to play our hand optimally against the part of his range we do beat

We only have a ~psb left. Our options are to break it up into 2 bets or just shove it now.

In favor of breaking it up into 2 bets:
1. If makes it harder for him to get away from 88-TT (18 combos)
2. Lower pairs are a big majority of his range so maybe we should focus our bet sizing on those hands

In favor of shoving:
1. He's probably not getting away from JJ-QQ (12 combos)
2. Even a shove gives him the right odds to call with big draws, but he might mistakenly fold them since "the board is paired" or "he can't go all-in on a draw"
3. If we make a smaller raise we have to get it in on any turn, which could get ugly if something comes off like an A, Q, J, or even a 3flush is kinda bad (Q and J are bad b/c they lower the likelihood he's getting it in with pps lower than that card

I prefer shipping it in

This is a gross spot. I think I can find a fold here.

I think we get shown an Ace or quads way too often. Since he raised the flop I think its less likely that he has 5s full.

i'm betting small for value, trying to get 99 / flushes to call.

River is bet-fold all day. You can and will get called by worse, and better will -always- raise.

I'd bet about $100.

Grunch:

Warning: my view may well be considered stupid/ weak etc.

I'm not happy about having to play 5-way here. If this was likely to happen, (as per bolded), then raise more- firstly for value and secondly because not many of us are good enough to play multiway pots without actually hitting.

As played, if it were me, I'd be saying that I'd gotten a C at best (more likely and F) for pre-flop play. I now need to rescue this hand by playing really well or getting lucky.

Well, we didn't do well at all pre- and I'd feel like we're letting this get further away from us on the flop. As you say, you could be way behind here- so what's the reason for leading out?
In V's place, I think I'd be raising you pretty much every time here, too. Now we have absolutely no idea where we are AND we've called a re-raise- the pot is now too big for V to get away from unless he thinks you're never ever folding.
And yet....

... V checks?
How is this board any worse for V?
You've said he's a good player- why would he check here?
If we think we can be winning, I presume we're checking in the hope he's going to check river, too?
How realistic is that given V as descibed?

So V has just put in half is remaining Stack on the river? I mean, guess he could have a random 5 or a pp you beat, but there are also six to eight Ax hands which make sense alond with 55 and a weird 3.
And your hand is pretty much face-up.

I don't know- it's hard to advise any action on the river because I don't think I ever get that far- I guess I'm shipping it on the flop mostly or on the turn if my read/ history justifies it.

On the river, I can go either way depending on detailed history you can't express in writing/ to those who weren't there etc. I may sigh call or, frankly, muck to punish myself for playing badly.

Never calling otf with this action, either 3bet otf or fold

As has already been said by a few guys, I think a 3 bet on the flop will get the job done, he won't have enough (and probably not good enough) to 4 bet bluff the flop and if he has you beat he's going to call your 3bet on the flop and we'll know that we're up the brown creek immediately. Seeing as we have got to the turn I would ship here, so difficult to put him on quads as a few have suggested as I don't see how there can be any 3s in his pre flop calling range, for the same reasoning I personally discount 55.

I think the river is payday for him, sucks to be us right now and IMO it's a bet/fold rather than a check/call all day long.

Thanks all for taking the time to reply.

I do like the idea of a flop 3-Bet - and I probably should have done so at the time. I was mostly thinking about the river decision after the fact, but in retrospect I think the flop decision to flat-call set me up worse. If I was in position and he had check-raised I think flatting would make more sense, but since I'm going to have a hard time picking up any new information later and the board is very unlikely to get better for me I should have 3-Bet him right there.

On the river as played, I think a bet-fold line would have made more sense. If he raises I don't think I'm ever good, but I didn't give myself the chance to win the hand.

As it stands, I thought for a really long time and folded my Kings. He mucked, so I have no idea what he had. I could see him bluffing in this spot, but I didn't see him value betting with worse very often. But by checking to him on the turn and river I didn't show any strength, so I put myself in a position where I was begging him to make a bet on the river and put me in a tough position.

Without going into details that nobody cares about, I should have left the table a couple of orbits before this. I was feeling tired and I made several mistakes on this hand in my thinking that I think were due to lack of concentration. Part of the reason I posted this one was because I beat myself up over the hand for the next day or so to the point where I'm not sure that I was thinking objectively about it. I wanted some less biased observations, and I feel a little bit better that I can use this as a learning experience now.

Thanks again!

FWIW, I did not expect to get 4 callers betting $16. My standard raise had been more like $12. I figured the original limper would come along (folks rarely limp-folded in this game), and maybe 1-2 others. Betting $20 PF would probably have killed all of the action - not sure why, but it seemed like there was a psychological thing with a bet that started with a "2". The PF bet is probably one of the few areas of the hand that I feel good about.

I should have written this better in my original post, but at this point I thought I was likely going to take down the pot with my bet, and at worst I was going to get called by a flush draw or a lower pair, which was fine with me since I had bet enough to charge a draw. It was only after his raise that I thought I was in a way-ahead/way-behind situation.