V is a competent winning player. He's currently high, just kind of chilled out. Have bluff caught vs him before down to the river and he is definitely capable of running triple barrel bluffs. I played a few hands versus him when he was CO/BTN and I was SB/BB. had K9s called his bet over straddle, x x flop, x x turn, i bet half pot on river he calls and i win. Another time had K9s again board is AQ5 with my flush draw. I x he x. turn is offsuit 2. I bet 35 into 70 he raises 120. i Call. River is 5 that gives me flush so AQ525. I x he bet 300. I call and win vs AQ, so he has some slowplays (the x on the flop with 2 pair). Another hand vs him Had a gutshot flush draw on an AKx board and called flop and turn and folded to 2/3 size bet when everything bricked on river. Have also had some friendly conversation with him, but I've always let him/he's always ended up being the aggressor thus far. He's not too scared to put money in the pot by any means, was telling me about some 5 figure pots he lost in other games. He's also seen me bluff check raise tonight early on in the session to 500 with a gutshot on the flop multiway and then call a small shove over the top, all my other hands were tight and for value tho, have showndown AA, KK, flushes with suited broadways, etc.

OTTH:
Limper or two, V makes it 30 on the btn. Hero in BB with 98cc calls. one MP limper calls. Board is 553hcc. limper x, V bets 50. Hero calls MP calls.
$240 to a turn of (553hcc) 9s. hero x, mp x, V bets 150, Hero calls, MP folds.
$540 to a river of I forget the exact river, it was an offsuit 7,6,4, or 2. So basically a blank unless he was bluffing with A4s or A2s and nailed a straight if it was one of the wheel cards.
Hero x, V bets $350. V has $2,100 behind hero covers. Hero?

Why bluff with sdv and holding the clubs you want him to have? Sounds value mergey. Maybe you were just ahead here? Say he has ak no clubs or one club that's a hand he can absolutely bet this river with. You have other hands you can raise with like 67h that called flop with bdfd , got a double gutter then bricks or even hit as we don't know the river.

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I'd raise the flop - you have the best range advantage on this board given you're out of the BB, and of course with the FD we can make the best hand. River looks good but I don't think I'd rip it - think going to 900-1000 has a similar effect and doesn't require you to win as much. The bottom line is he's trying to value bet an overpair and this board is so favorable to a BB range that you can easily have FH's raising here/straight/whatever. The one obvious thing is the flush draw missed, so he could talk himself into calling a fair amount. Either way prefer raising the flop rather than this line.

Flop is where you want to check raise bluff here. You called from BB so you can have a lot of trips combos he needs to worry about and you have FD, 2 overcards, and backdoor straight draw.

I would let it go on the turn. On the turn when he bets again he most likely has trips himself w A5s, an overpair, or a bigger flush draw.

As played I dont want to bluff river here with clubs.