There's a chunk of relevant history and some solid guesses that we can make about Villain in this hand, so bear with me for a bit. And really I'm looking to start a discussion about the best profit-maximizing line, both on the flop and planning for later streets.

Villain is mid-20s, grinder-looking player, wearing hoodies and sunglasses. Has been playing with Hero for 6+ hours. Overall seems like a very solid, good thinking/winning player (meaning has no obvious leaks, sizes bets well, understands value-betting/bluff-catching/position/relative hand-strength/etc. all that good stuff). I have every reason to believe that Villain has also been observing me as much as I have him, and he probably sees me as being a similar player type as himself, except that I'm probably a tad looser/more aggressive than him, and that I tend to size my bets a little bigger than him as a general thing.

There's probably 4 hands of relevance to the main hand in question:

1) Within 15 minutes of first sitting down, Hero decided to 3bet-squeeze a $15 open from Villain after 2 weak calls, to $85 w/ K6ss. Got cold-called by the SB and Villain called as well. Flop was As5d6h, I cbet $145 when checked to, the SB called, and we checked it down from there; SB showed AQo and I mucked. Was surprised by the cold-call with AQ, but shrug w/e, made a note and rebought.

2) Exactly 2 hands later, I 3bet an older player's $20 open to $75 w/ AKo, got cold-called again by a different SB player, and the old guy 4bet to $325. Normally this is probably a fold, but the table had talked about wanting this player to stick around cuz he was fishy/spazzy, so I figured that 5bet jamming AKo for ~120bb wasn't the end of the world here based on that (also sizing seemed weird for KK/AA but I wasn't reading a lot into that). Mainly I just figured I looked really fishy/tilty, so w/e let's flip. I jammed, he called w/ JJ, and I flopped a K. Old guy proceeded to tilt off about $1500 afterwards, so that was cool.

3) Back to Villain with this hand, he opened to $15 pre (his standard), got 5 calls, and flop came 874dd. Villain underled for $30, one player raised to $75, Villain reraised to $150, other guy made it $350 total, Villain makes it $700 total, and the other finally folded even though he only had about $400-500 behind (!!). If I had to guess, I would put Villain on the nuts/super-nuts here (76dd). I didn't think they had enough of a dynamic for him to be 5betting here with a nut/combo draw and expect to get a fold, especially cuz the other guy easily has the nuts in his own range and/or would just call it off with a set to draw at his boat, given the price.

4) Ok, this hand is actually between me and the Villain. Villain straddled to $10 on the button, folded to me in the BB, I open to $35 with 88, and pick up one MP caller along with Villain. Flop came Q76r, I decided to cbet $50 into ~$100, knowing that everyone expects me to cbet nearly 100% here, and figuring I was going to get called pretty light or just straight floated by airballs/gutshots. MP folds, and Villain tanks a bit before calling. Turn is a 3, rainbow board. I check, expecting Villain to bet all his floats, and he obliges for $75 into the ~$200 pot, and I call. River is a J, which actually hits some of his floats, but I can't really do anything but c/c, and Villain bet again for $160 into ~$350, I tank for a bit before calling, and he turned over 53ss. Before this hand, I had been bet/folding or bet/giving-up-on-turn a lot w/ my cbets, and I feel like maybe the table thought I was just habitually firing one barrel at every board (really they were just good textures for me to cbet, and my opponents kept hitting pairs or better).

---

On to the actual hand:

Hero is MP w/ ~$1800, opens to $20 with 88. Folds to Villain w/ ~$1500 who 3bets to $55 from the SB. I think 4betting is an option, and being this deep and in position, we could probably get away with it just fine, but I chose not to. If someone wants to talk about it, I'm all ears, but I think flatting is obviously a fine option.

Flop: J 8 5, pot: $110.

Pretty bingo flop for us, wet enough to entice action from a lot of hands. Villain leads for $30 (seems to be his trademark to underlead spots like this, and I fully expected him to reraise me a high % of the time). I make it $130 in-rhythm (thoughts on this sizing?), and Villain takes maybe 5-10s to make it $280 total. Counting our bets so far, pot is now $520, and we have about $1200 left to bet.

Who flats and who reraises?

If we flat, what to we do on 4/6/7/9/T/Q/K/A/heart turns? How often does Villain have a draw vs JJ-AA here? What do you think the min-3bet preflop means (never seen him 3bet for this size before, have seen him 3bet once or twice for normal 3x or 4x sizes after a bet and 1-2 calls, and people just folded; always just assumed he had the goods).

Raising is obviously a very good, +EV play, and I think it's safe to assume that raising by default here can't ever be bad. But is it the best play? If Villain doesn't have many draws because of his preflop, OOP 3bet, then flatting is much, much better right?

There's just so many things going on with this board that I had a hard time figuring out my turn/river plans, based on how the hand might play out if I flat or if I reraise.

Hmm.

So there is obviously some action between you, he 3bets you in the SB... I would figure that the 55 3bet from EP means that he has a hand he likes and is definitely wanting to keep you around for a flop. I'm thinking of about a range of 7-8% for this 3bet? That would put him on A10+,QJs+, and 88+.

Obviously at this point you are crushing everything besides JJ, and are at about 90% to win this hand with a top 7.4% range for villain.

I like your raise size, I think his raise to only 280 is pretty weird, I'm not sure if he was on a draw if he were to flat your raise or if he is prying for a raise from you.

I would Re-raise to 650-700 in this spot. I'm jamming basically any turn if he flats my raise, if he jams your raise I'm getting my money in there as fast as I possibly can.

Very interested in what other guys think about this spot.

so. many. words.

Lol I know, sorry, just see so many hands where the reads provided are really inadequate and we're always making guesses in a vacuum about what to do. Figured maybe some people would appreciate having some more real reads and history to go on.

Fwiw, I think 4betting pre is pretty terrible. I have no idea why you'd consider that.

I probably make the first flop raise a bit bigger but not a big deal.

Whatever we do here is going to look incredibly strong of course. If you think he'll put you on a draw if you 4bet, then do that. But I'm generally flatting because I don't see how he can call with AA if we 4bet.

Pretty much just shipping the turn if he bets. Obviously betting if checked to.

HU, I honestly think this weird line could be a bluff relatively often, so I don't mind letting him barrel.

I agree that it's often a bluff, but if it is, I don't necessarily think he will continue on the turn even if I just flat. It might still be a risk worth taking, because like you said, reraising here probably folds out everything that's not a combo draw or a set. But I REALLY don't want to see a bad turn card, and I think 50%+ of them are bad. Is that fishy?

As for 4betting pre, I think this deep I just feel like abusing our positional advantage is rarely a bad thing, and 88 plays pretty well post-flop imo. If we 4bet and he flats, we can cbet a lot of dry boards and win, or check-behind and bluff-catch, or flop a set and win a bloated pot (because 300bb deep, even a 3bet pot won't easily get stacks in, we basically need the 4bet for that). If he 5bets, we may still be able to set-mine (I'd make it ~$100, he makes it $200, we're calling $100 more to win $1300 behind?). 4betting gives us a really good chance of beating out his medium-but-better-than-ours-pairs 99-JJ, makes it tough for him to play any random broadway cards he has from OOP, and overall opens up our 4betting range (not an immediate concern, but builds dynamic for 4betting premium hands later). I'm not saying I'd do it often, but I don't see how it could be all that terrible.

88 has a lot of value. I'd much rather turn another hand into a bluff. The reasons you list (plays well post-flop, can set mine against the top of villain's range, abuse positional advantage) are all in favor of flatting the 3bet and playing a less bloated pot in position, imo.
There are just much better hands to use to open up our 4betting range, if we even need to be concerned about such a thing. We have position so it seems better to aim to play postflop anyway.

There are a lot of bad turn cards but we have a better chance of getting value from QQ-AA, Jx if we flat, imo. We should stack 55 no matter what (can he even have that here?). There shouldn't be -too- many draws in his range.

i like the hh w/ descriptive reads, makes a big difference when deep.

4b 88 would be pretty bad imo, and flatting is really good. 88 isnt gonna play so well in 4/5b pots, and does poorly vs those continuing ranges. i would personally prefer to 4b a number of suited 1/2 gappers and QQ+

flop action is pretty interesting. his lead sizing (and 3b sizing) is horrible, but yours is not great either. its a pretty significant mistake not to make the raise bigger here, especially considering you have a strong read he chooses this size to induce/then 3b. its a very dynamic board, you are in position and 350bbs deep, your whole raising range should be choosing a larger size, id go to like 180.

i would probably flat his 3b, you have all the sets in your range and hes probably gonna assume that they make up most of your flop 4b range here, plus you mostly wanna flat with a lot of draws or even some slowplayed overpairs

ott, jam over his bets on any non flush/non A (just flat those). if checked to obv bet all brick turns, probably actually check back flush turns (although i think its close) because your range strength has improved so much and sets are now much lower in relative value; you now have plenty of flushes to valuebet ott. checking back may induce some thin value from overpairs and some bluffs on the river as well

I look at his pre-flop sizing a little differently. Presumably you have folded to at least a few 3-bets in 6 hours. With at least 1 tight player in the blinds, your MP raising range when folded to is viewed as somewhat, if not very wide. He's going be re-stealing some with suited non-premiums (T9hh, 67hh, A5-7hh, A9hh, AThh, K5hh) and is also probably happy to play 55 with initiative and 3.7% of his stack in pre.

Can you describe BB's game a little? He's kind of important, given its just the 3 of you with cards left.

On the flop, I like $150 better. You mentioned you expect a b/3b a high%... How dramatically do you think that % changes if your raise is to $200?

kinda ridiculous the amount of "bad" turn cards you are counting here. 4,6,9 and T are bad cards why? because he can somehow make a straight with them? Range him on a 3b from the sb, is 67ss and 910ss in his range? If so he must have a pretty high 3b %, and I might just 4b preflop. I just reraise to 620ish and try to get it in, might be sacrificing some ev but i dont really care. Give him a chance to make a huge mistake

I think it's important to factor in how he views you. You mentioned that the table thought you were "one and done' does that mean that any 4 bet from you would be perceived as the nuts only?

I ask because in almost all cases I'd raise here. flatting leaves a strong villain w/ the lead going to the turn, where I hate half the deck and likely have to play a monster like a bluff catcher and just call down. Over two streets this deep that could certainly get pretty gross quick. Conversely, if he has a one pair hand it's likely he slows down dramatically on a bunch of turns. It could be just as hard to get paid off as it is to be put to a serious test on most run outs.

While his pre flop line seems to be big pair/valuey, I'd think he's good enough to play his whole range like this and could show up w/ 7h9h just as easy as he could KK. It's worth noting that you thought he had a SC the last time he took the weak lead/3bet line.

As long as your image isn't such that a 4bet is viewed as sets only I think we need to raise. The board is such that you could have QhTh or QQ when you take this line. I think he's obligated to call w/ most of his range once he takes this line. I want to get as much in on the flop as possible. At worst we put him in a bad spot oop w/o initiative ott. At best we gii on the flop crushing everything other than the 3 combos of JJ.

I think a healthy flop raise here gives you the best chance at getting his stack. I don't think he folds to our flop raise often. I do think he bet/folds or check/folds a lot of turns. If he's putting in a bunch of money on later streets chances are our hand got drawn out on.

Raise to $575.

From your hand #3, IMHO this Villain under leads/re-raises when he has a strong(ish) hand and he is not giving up on the hand easily. Why not continue to build the pot right now while he is still willing and not ready to shut down?

I don't think V has any bluffs here when he 3bets flop. If he does it's really spewy as we can rep hearts/straight on turn/river much better than he can and what made hands is he expecting to fold out when we raise the flop?

As for flatting or raising flop I think there are too many action killers on turn/river and we should raise now. Any heart, J, 7, Q, A. He can easily level himself into thinking we're on a draw and plan on stacking off on non heart turns. $625 looks good.

Interesting spot, I think raising here is best since in his eyes you are aggressive and it would be consistent with the image and I think he definitively has hand with some equity when he re-raises you on the flop.

As played I'd raise this to 600$ and shove turn or snap call if he jams.

Gonna try to condense/summarize/address things all at once:

1) Preflop

- You guys think 4betting 88 pre is bad/marginal as default. Can find better hands to turn into bluffs. I get it.

- I think Villain expects me to flat his min 3bet very wide (i.e. probably expects me to fold ~0%, bluff-4bet some small %, and play the rest of my opening range standard-ish, as in flatting 88 and 4betting AK/JJ+, etc.). I think he just assumes it will be heads-up pot, as BB in this hand was a standard TAG-ish player who wasn't going to cold-call very wide I don't think.

- I do believe this Villain is very capable of having everything that connects with the actual flop in his 3bet range, like AXhh, 56hh, 97hh, 76s, T9s, 55, etc. along with the obvious top ~5% hands. I think it's a question of frequency, because he's certainly not 3betting 76hh every time here vs every MP open, but vs me he might do it pretty often, since playing small/medium SCs from OOP without initiative isn't really ideal.

2) Flop

- Looks like you guys mostly wanted my first raise to be a little bigger, given that we expect to be reraised very often. Fair enough, I can see $150-$200 being better. Our sizing does have to be consistent/balanced vs this type of Villain though ofc, so we're making pot-sized raises with all of our draws as well yes? No reason to get cutesy with smaller raises, or polarizing with certain parts of our range (i.e. big raises with bad draws like gutshots/Ahx blockers/nutted hands, small raises with good draws/medium made hands)?

- As for whether we're raising or flatting, it seems we can break it down into 3 likely scenarios based on Villain's range:

A) he has QQ+ and will find it hard to continue to a 4bet from us on the flop (but not impossible)
B) he has a good combo draw/NFD, and won't fold to any reasonably sized 4bet
C) he's bluffing with an airball or a weaker draw (gutshots/bare flush draw)

- We should definitely flat in scenario (A) I think, because I assume that a player of this caliber won't go crazy with one-pair, and whether he likes it or not, will default into the mode of thinking that at 300bb deep, I will most likely be playing a value-heavy range (i.e. with QQ-AA he's not really happy to call/gii vs my good draws either, and when faced with a flip-or-way-behind situation, he'll probably find a flop fold). Vs (B), the obvious answer is 4betting the flop, but I think there's some merit to flatting here too, assuming he fires on brick turns with his draws (and if we just flat, the pot is smaller and we may be able to call a turn bet to draw to our boat, whereas 4betting the flop guarantees that he'll probably just bomb a flush card on the turn if he has it or decides to bluff with the Ah blocker); in my mind I see it as like a 70-30, 4bet vs flat mix for this situation, in favor of 4betting. (C) is trivially a flat.

- So now we should assign relative probabilities to each scenario. This is what I'm struggling with, as I've thought more about this hand. If he had made a standard 3x-4x preflop 3bet, I think we're looking at (A) maybe 80%+ of the time, and scenario (B) would only be AhKh/AhQh type hands. But as played, if I really had to guess, I'd say it's 50% (A), 40% (B), and 10% (C) or less. Looking at it this way, I think flatting is marginally better???

I prefer a jam on flop for 2 reason:
1) villain preflop and flop line seems made hand to me rather than a drawing hand
2) a lot of turn cards are not worrying by us but for villain, if we flat the flop we are repping a drawing hand, any scary turn will scare villain away not to mention he is scared like ass already when u flat the flop.
3) a jam is more preferred than a 3bet is because a jam would lead villain to think that we are willing to gamble with our draws and may induce a hero call from him.

1. i think your preflop analysis looks good, although i think he probably expects folds from the bottom ~30% of your range, depending on how wide you open (and how wide he thinks you open). you guys are deep, and i'd expect him to have those hands a non-zero percent of the time here too, especially with no limpers/callers, so he is probably not declining the opportunity to play a multiway pot with weaker players. however, you should discount those combos bc as you said he isnt always 3b here with them. if he is 3b TT+/AQo+ for value (62 combos) and overall about 8% 3b in this spot (seem reasonable?), that leaves him with ~40 other combos of suited connectors/one/two gappers and Axs/Kxs that he chooses to 3b. if you think he 3bs more/wider, adjust flop analysis accordingly. i also think that if you decide to 4b 88 here, it could only be because he 3b so high (~20%?) that you can 4b for value- bluffing with 88 is absurd.

2. flop thinking process looks good too, although i would be wary of the scenario weighting system you are using distorting how his range is actually made up on the flop. for instance, using the ranges above, he has 21 combos of overpairs/sets and 12 combos of flush draws (40/4 suited combos + AKhh/AQhh) to account for all of his flush draw semibluffs, not all of which he would necessarily b/3b the flop with, and only some of which are combos. it should also be noted that while he does get to the flop with some flush draws, you have many many more in your mp open/call small 3b range, so i wouldnt be too concerned with him running bluffs with Ah and exploiting you, and you also need to consider how many of these draws want to play this flop against his 3b, and having sets in your range going to the turn is pretty nice. i think flatting is considerably better since he will also perceive your 4b range to be super unbalanced and filled with mostly sets/a few combos, and will make few mistakes (this perception is also likely true, at least it is against most players). if this was a reverse post and you got 4b on flop as villain, consider what hands people would advise continuing with.

IMHO

No, I don't agree with this. While I agree with your reasoning and yes he will have a hard time to continue, the rest of the hand will be awkward to get your stack in as many turn/river cards will shut him down vs few that won't. If you believe he can find a fold on this flop then he would find it even easier on any , 7, 9, 4, 8 turn/river card after you flat.

A) He does not know you have a set.
B) What makes you believe he will fold to your 4bet. Look at hand #3.

If you 4bet and he folded I would not worry about it one bit.

This.

Shortly put, even if he folds to your 4bet (which I do not think he would IMO) you honestly would not of got much more (if anything) on the turn. (although there is a good chance that YOU can get put in a sh*tty spot Ott)

I think people have covered most bases that could be covered, based on available info, so I may as well reveal results:

I thought for maybe 15s-20s (didn't want to tank too long), and decided to raise him $350 more by grabbing a stack of 20 green chips (i.e. dealer had pulled in all the bets, so I grabbed $500 more). I thought this was the most "natural-looking" bluff sizing, that I was just grabbing a convenient stack of chips. Villain folded after not much thought; I'm pretty sure he was happy to take a bet/fold line with QQ+ here, trying to charge some value from my draws with his reraise and hoping to bet a blank turn, but willing to give it up vs a raise from me. Obviously 4betting my draws or just airball bluffing here more often becomes hugely profitable if this is his default line; in fact, I really wished I had a hand like QThh or 65hh instead.

I think when I was playing in the moment, I assumed that his min preflop 3bet meant that he was manipulating his range somewhat, but the more I think about it, the more I feel like it was just his standard size basically heads-up vs me. There's not really a huge point to making it $100 or $150 or w/e, since I can still set-mine in position at 300bb deep, so he might as well go smaller with a wider range, and then hope to surprise me post-flop when he hits something that maybe he thinks I won't expect. Basically, at the time, I thought he was somewhat less likely to have JJ+ and more likely to have a draw based on the sizing, but looking at it now, I don't think that's true at all.

I do believe we have to be able to have sets in our flatting range vs thinking players, but I still don't know how or when to decide if it's better than raising (because obv raising is fine and good and +EV).

Very nice post OP. Great detail.

What is Villain's value range here after all this history and action?

Can we eliminate 55? Is he 3b from the SB with this?

Should we include T9? Is he 3b from the SB with this?

Obviously, Villain can have JJ+, AK, etc.

IDK... it doesn't look like a spot where we want to get fancy. If Villain does have something like T9 then he's probably not folding and we're going to get it in OTF. But FD's are probably only a small part of his range.

I think I like your line best. 4b the flop and keep getting $$$ in the pot while we're still pretty far ahead, and while we want to avoid any scare cards killing our turn action.

NH.

ETA: Do you think he's folding QQ+ to your 4b here with high frequency?

IMHO.

When I am in position on dry flops and V is showing/continuing with aggression and building the pot for me.

EG: J83r, J28r, 844r, 823r, T82r. ... Based on pre-flop -> flop action, a raise here may mean a low PP pre-flop, set on the flop from my Villains point of view if my image is a solid/standard/ABC player. If my image is "fishy" a raise may mean TP/?K and we still GII vs over-pairs.

Did V show his hand?

NH and WP.

Four betting pre-flop is bad this deep. No real reason to turn your hand into a bluff, and you obviously don't want to get it in here. His range from the small blind is probably much tighter than normal, so you definitely have solid implied odds.

The flop is an easy four bet. There are just SO many bad turn cards that folding out his air is necessary to avoid terrible turn and river spots this deep. Make it 650 and shove any non-heart turn.

Reraise.

Jam any further raise and all non-draw-completing turns.

I really do think he's folding one-pair a lot on the flop, and I think it was a function of him seeing me take good bluff-catch or thin-valuebet lines, but never really seeing me make a big bet or raise postflop without showing up with more nutted nuts.

Like, clearly he knows I'm capable of bluffing/semi-bluffing, but gameflow-wise he probably thought I was leaning tighter than I really was. In that sense, I thought I was "unlucky" to not have a draw here, if that makes sense.

I do think 55/T9hh/etc. hands that aren't normally in his 3bet range might creep in vs me, just because he doesn't like how those hands play out if he c/c from OOP. I wouldn't bet my life on it ofc, but it's one of those things where I don't think it's accurate to say, "oh he clearly 3bets 10% or 15% here." I think he's capable of picking and choosing premium hands as well as pp/scs/etc. preflop, rather than just taking the top X% of hands or w/e.