$2/$2 NLHE, local underground game. The game is 7 handed at this point, and we’re fairly deep.

V1 (UTG+1, $500) - Middle aged white guy who is without exaggeration the loosest, most maniacal player I’ve ever encountered. Likes to make huge raises and always capable of having anything from the nuts to complete air. Very rarely folds any pair or draw postflop for any amount of money.

Example hand history with V1 from a $2/$5 game several months ago: V1 straddles UTG for $10, 4 people call, I flat from the CO with AQ, BTN calls, both blinds call. V1 raises to $80, folds around to me and I shove for $450 total. Folds around to V1 who quickly calls with 86. I hit a Q on the flop and hold.

V2 (BB, $350) - White guy in his early 30's. Decent aggressive player, does well in tournaments from what I understand but can be a bit spewy in cash games. Like V1, V2 is known for making large raises with both his semibluffs and his made hands. However, V2 is nowhere near as maniacal as V1.

Hero (SB, $325) - Also a white guy in his 30's. Viewed (correctly) as the tightest player at the table tonight. Normal nitty image is enhanced due to the fact that I’ve been card dead all night and have barely played any hands in the past two hours.

On to the hand: the whole table limps. I’m in the SB with 87 and check my option. BB checks as well.

Flop ($14): 456
Sweet, I flopped the nuts. I would normally lead out in this spot, but this time I decide to check, figuring there’s a good chance V1 will bet and I’ll be in a great spot to go for a check raise. (Because of V1's image, his bets get called super light, and if someone has like a pair+OESD type of hand they may even raise him before the action gets back to me.) Much to my dismay, it gets checked through.

Turn ($14) 3
I lead out for $12, V2 raises to $40, V1 folds and everyone else folds. (V2 is definitely capable of making this raise if he picked up some kind of backdoor flush draw. He’s also probably doing the same if he hit either end of the straight - he was in the BB, so he can have 2's in his range here.)

I think if I take a bet/3bet line here, villain going to put me on exactly what I have. So I decide just to flat. My plan at the time was to check most river cards in order to allow villain to bluff with his missed flush draws or to value bet if he happens to have a straight.

River ($94): T

Hero ???

In addition to the river action, I’m really interested in feedback/criticism on my line up to this point. I normally would fastplay this hand on the flop, but does the presence of V1 in EP (with a bunch of people still to act behind him) make this a good spot to go for a check raise? Or should I have just led out myself to start building a pot up early?

The situation obviously changes on the turn when V2 raises us and V1 folds. I really wanted to put in a moderate 3bet here to make it easier to get most of our stacks in on the river, but this villain knows my game well enough to know that I’m very likely to have the nuts if I re-raise here. Since I think he has a lot of flush draws and possibly low straights in his range here (and I think he will bluff big on the river with his missed draws if he can put me on a marginal hand), does it make sense to just flat the turn raise?

If your read on how the other villain's perceive you is correct, as played you should check raise the river expecting to rarely got called.

I think leading the flop is definitely the way to go, even competent villain who know how tight you are aren't going to put you on the nuts. Even if they know this is usually a made hand, they could have a draw with what they think has a lot of equity. But this hand highlights why it's important to sometimes semibluff so you're not so unbalanced in these spots and can get full value. You don't need to be remotely close to balanced, but if everyone knows you would never leave with a 7, two overs and a bdfd, etc. it's near impossible to get paid here

I think I like a lead on the flop given both Vs' descriptions. If they hit anything they are at least calling if not raising. I don't mind the check, though, and you thought it through fine. Actually, a check/raise here might have been too strong unless they had two pair / set or a straight.

Turn is good if you think V might fold to a raise. I'd lead river ~$50. It would be sick if he checked behind.

As played, I think we check/jam the river, as given our reads he will bet most of his range here.

I think I would put in a small 3b on the turn though. I don't want to give him a free look at a semi bluffed flush draw, and I think he will call with a lot of worse straights and 2p. To me, these factors outweigh any advantages we get by disguising/widening our range. I don't think this puts us face up either. We could easily do this with any 7x.

I like to lead flop as opposed to C/R flop here just bc C/R will shut down a lot of action.

As played, i'd lead river here because you'd get call by a lot of hands here since both FD missed and you'll get a call from 2p-set-7 here putting you on bluff. You miss out on a lot of value of checking river here because 7 will rarely bet thinking it's chop pot and 2p/set will prob check back as well in fear of a 7.

Lead on the flop. A c/r is too strong from a tight player and everyone will know you have a straight. A lead could be interpreted as TPGK or some kind of draw. You also can't waste a street building a pot because there's so little money in to begin with.

I would reraise the turn. Calling a raise on a 4-straight board is already a strong move. You might as well try to play for stacks.

Bet the river. V2 may have enough to call and maybe raise. Max value on every street.

Pot or overbet the flop. 3bet turn omg, or do something sexy and jam. He's not folding 7x.

The pot is so small otf that I'd go for the c/r. If you lead $10 into $14 and get called in 1 or 2 spots, it doesn't do much, so I'd take the chance at the c/r to get the pot bigger ott. These guys aren't b/f'ing otf so if there is a bet, they're b/c'ing. So if it's X% to check through, X% of the time the pot will be $14 ott. And (1-X)% of the time, there will be at least a PSB and you c/r to $50 and get called, so (1-X)% of the time, the pot is at least $114 ott. So I'd take that chance, and by what you tell us about the Vs, it was unfortunate but not likely to get checked through. Oh well.

OTT definitely raising when it gets reopened. He's not folding 7x/flush draws/2pair. The thing is fd's have the most outs and will beat you if they get there, so you just need to raise to an amount that prices out a fd. It's tricky being oop because unless you plan to c/f all club rivers, you're giving V implied odds, just a factor of not having position. So the raise size is really important. If you raise to $120, V is getting direct odds of 80/(120+120+14) = ~31% and he only has about 20% equity with a fd. So he's behind and to even give him incorrect implied odds, you could b/f $145 otr if you feel he only raises a river club with the flush. Even him getting that $145 off you otr doesn't justify his turn call with a fd. However, you'd be betting $145 of your remaining $203 and that's insanity. It's definitely awkward, but betting $10 otf wouldn't have made it that much less awkward, so I still like taking the shot at c/r'ing otf. So I'd raise ott, to about $120, shove all non-club rivers, if a club hits and you feel confident V is only raising the river w/ the flush then I'd b/f about half your river stack, ~$100. When you make that leverage bet, V can't think he has any FE so bluffing is probably out of his arsenal. It's not ideal but it's a factor of being oop, things won't be perfect.

As played otr, I'd bet small to induce. Again, not ideal but there are a few good things that can/will happen. Bet $35, for example, and the showdown value part of V's range is calling, so you get$35, worse things can happen. An overbet is only getting called by 7x and if V has 7x, he'll raise your $35 river bet anyway, so no need to overbet. And since you're only betting $35 of an effective stack of $283, V can definitely think he has FE by raising, and he'll bluff raise with plenty of his missed hands or maybe even turn 2pair into a bluff if he convinces himself you have the low end of the straight. Or he might do it with anything if he tries to get you off a chop, pegging you for 7x.

Grunch:

Hard to go wrong with pot/pot/pot esp at low levels where calling ranges are very inelastic with regard to bet sizing.

There is no less than 16 turn cards that can either kill our action, give us the worst hand, or just generally make it hard to get stacks in.
Also, with a super agro we'd love to bet out and get raised otf. That would be sexy.

As played, 3bet the turn to $80 if you think he is weak $115 if you think he is strongish.
Then 1/2 - 1/1 pot the on teh river depending how fast he calls the turn bet.

As played, either pot it or ck/rs something big depending how often he will turn sdv into a bluff otr. I.e. if he will bet bottom two, top pair, over pairs here otr then def ck/rs. If he will check back those hands, then bet.

*grunch*

I hate not betting flop here. 150+ BB deep means we need several bets and at least 1 raise to get stacks in. There are a ton of hands that will call bets here,so just lead out. If everyone is instafolding the second we look at a pot too long then we need to up our c-bet frequency.

The way we play turn is going to dictate our river play. If we think he has more flush draws in his range I would prefer a 3-bet OTT for value. Then we can just continue with our aggressive line OTR and hope he spazzes. If we're just calling his raise we should probably just check river hoping he decides to bluff at it. He probably won't at this point because there's so little in the pot and we're going to win the minimum.

It's 2/2 with Vs who raise often, just value bet and print money. No need to try and get all tricky with passive flop lines. If no one has anything, oh well, move on to the next hand and hope our image looks a bit looser for our having taken down a pot uncontested.