$2/$5 underground game. Small player pool, everyone is familiar with how everyone else plays.

V1 (CO) - White guy, late 40's, absolute maniac. Normally characterized by super aggressive play, but also capable of calling down with extremely marginal holdings. Will call large bets on the flop and turn if he believes he has any outs, but will fold river if he doesn’t hit anything. (Example from earlier in the session: V1 raises to $35 on the BTN over a couple of limps, Hero 3bets to $105 from the SB with TT, V1 calls. Hero bets $140 on a 542 flop, V1 calls. Turn 6, Hero moves all in for $175, V1 calls with KQ and the river bricks out.) $1000 stack.

V2 (SB) - White guy, early 50's, tight passive ABC player. Rarely gets out of line, but has enough experience to recognize spots to cbet bluff and stuff like that. $400 stack.

Hero (BTN) - White guy, early 30's, nitty/TAG image. Stuck a couple of hundred for this session after getting it in with a set against top pair on the flop early on and losing to runner runner flush. Has somewhat built his stack back up since by playing a tight range and value betting against loose passive villains. $900 stack.

Hero is on the BTN with JJ. 2 players limp in MP, V1 overlimps, Hero raises to $35, V2 calls from the SB, the limpers fold and V1 calls.

Flop ($110): Q52
V2 checks, V1 checks, Hero bets $80, V2 calls, V1 calls.

Turn ($350): K
V2 checks, V1 checks, Hero checks it back.

River ($350): A
V2 checks, V1 checks, Hero ???

My flop bet is for value, really targeting V1 since I know he will call multiple streets on a Q high board with tons of hands that can’t beat JJ. V2's call worried me a bit as he definitely has a lot of Qx in his range here, but he can also show up with a mid pocket pair or even AK, as I don’t think he ever 3bets any of those hands preflop.

I was planning to bet again on the turn, but I felt like the K was a terrible card for me. First of all, it makes it less likely that V2 will continue to call down with lower pocket pairs because now he can’t beat AK. Then there’s the fact that V1 is definitely capable of check/calling the flop with a unpaired Kx type of hand that now got there on the turn. So I decided to check it back and see what happened on the river.

Now that the A comes on the river and it gets checked to me, I’m wondering is this a good spot to turn our hand into a bluff? I feel like we have very little showdown value with three overcards on board, and I think V2 will fold all of his single-paired hand to a bet here. V1 is never going to fold anything that beats me, but there’s a chance he just doesn’t have anything.

So, bluff the river, or just check and see a showdown? And if we do bluff, how much?

If v2 is tight passive then he's likely in with a face card or ace and will not fold unless your bet is huge, which will be fishy anyway since you check the turn. The bluff would be repping ace-face or JT. Passive players and player like you describe v1 are hard to bluff off hands so I would keep bluffs rare and try to keep the investment small. I think you should be happy to get to showdown here as I doubt a K or A ever fold to your bluff and hands you beat aren't gonna call. Just check and showdown.

I think betting like $65 on the turn wouldn't has been bad but also agree that the K was a bad card. Luckily they check around the river and let you showdown without risking more chips. This hand is one reason JJ is a harder hand to play.

Yeah, this is a tough spot, but TYHIAB seems slightly better to me. You won't be good too often at showdown, I don't think. A bet of $175-200 would probably be big enough to get Kx or Qx to fold.

It's a close spot, though, given the way you described V1.

I would just check. You have a lot of leverage on V2, but V1 is not folding a winner very often.

What a weird hand. I can go either way, but I'd probably just check with V1 in the hand. Can't believe he's checking turn and river with a decent hand, though.

This needs to bet on the river. I bet what I normally would to get value if I had backdoored into an A. Bet $135. V2 has a queen or something like 88-TT and is shutting down. If V1 is curious like you say he is, we can get a crying call from a similar range like 5x or 77-TT.

I love bluffing and winning dead money, but this is a horrible spot. Manuac is calling with a pair and ABC player can have rivered two pair here easily. Check and give up hope JJ is good