One of the best tables I have ever played at. I have optimum seating as I have a maniac whale (v1) on my right and a passive calling station on my left (v2)

Effective stacks are $1500

V1 - probably the biggest whale I have ever played against. Has been playing for 3 hours or so and is in the game for at least $5000 ($500 max game) He has made some big bets/overbets when he has a made hand on the river, probably because its nearly impossible to put him on much preflop as he will call/raise 52o just as easily as he will with a top ten hand. Hero paid v1 off earlier when hero flopped a double gutter, got there on the turn, but the river brought 3 to the flush. Villain overbet the pot (like 500 into 300 or something) and hero wasn't laying down a made hand to an drooler of this calibre. Unfortunately, v1 had a ragged flush.

V2 - just your average calling station, positionally unaware, can't see the writing on the wall when he's way behind or drawing dead.

PREFLOP
V1 straddled to $10, hero raises KsJs to $50. V2 calls, all others fold, v1 calls.

FLOP: $150, 3 players

7c 8d Th

V1 checks, hero considers a cbet but both villains will call with any piece of that flop (?? Opinions) v2 checks.

TURN:

Jh

V1 leads for $100, hero calls, v2 folds.

RIVER:

Jd

Hero puts hands on chips in an attempt to get villain to check, villain says, "let me help you out." And bets $600.

Hero is confused. Bluffing a broken draw? Betting a weaker J, although its the last J? Fullhouse with JT, J8, etc? A 9 for the straight?

Against someone like this I feel like I should practically fistpump at a bet like this vs this villain, but our previous history and the size of the bet in relation to the pot has me unsure.

So, hero...?????*

a fish with a very wide range gets chatty and overbet bombs a 4-straight, paired board after he's seen us pay off an overbet with a marginal hand.

I think we fold unless you've seen him take this line with a bluff.

(This could change a lot if you have reason to believe he bluffs in these spots with all his air, or like auto bluff-barrels whenever you check, etc).

+1

im positive you can find a better spot vs these players

everything you said about his tendencies points this to fold, pretty easy fold too imo, you have the best bluff catcher but you only beat so many other Jx combos, wait for a better spot hes gonna pay you off eventually

Fold. Not much else needs to be said that wasn't touched on by the first two posters.

results:

hero puke folds, but feels like the correct decision was made.