In general i dont bluff fish, but this just turned out to be one of those great spots imo. Would love your thoughts

2-3-5 nl
Hero tag 26 asian. $600 stack Playing very solid no bluffs abc 123.
Villian 30s indian $800 stack, typical loose passive fish.

Villian raises utg+1 to $20 preflop. He typically raises larger with his monsters. Already ranging him around broadways but not quite aa-kk.
Solid tag Mp calls
Fish hj calls
Fish lj calls
Fish Btn calls
Sb folds
Hero bb calls with J9cc

Flop $120
Kh Jh 8c
Hero checks
V cbets $40
Solid tag mp calls $40
The rest fold to hero.
I think calling $40 here oop with second pair its going to be difficult to win the pot. And sensing weakness from villain due to his small bet size, and knowing solid tag will lay down any hand to hero's raise, hero decides to check raise to $240. We also have some good bd draws.

Unfortunately villain snap calls $240
Solid tag mp folds.

Turn $640
Kh Jh 8c Ah
Feeling like this Ah isnt really the best card to continue with. Alot of villians range just picked up two pair, or a straight draw. And villian is definitely fishy enough to call with any of those hands. On the other hand, Villian shouldnt have too many flush combos in his utg raising range (ie hes not raising 54hh utg), but he could have picked up Qhigh or Thigh fd.

Even then hero decides to check giveup, as villian is unlikely to fold.
Hero checks
Villian checks

River $640
Kh Jh 8c Ah Th

Okay so villian checking behind turn weakens his range somewhat, although many weak villians auto check back whenever they see a flush on board. Having said that, i think villian may bet some of the time if he picked up a fd on the turn, or if he picked up two pair. His hand is looking pretty weak, and with the Th coming on the river, we can now remove almost all flush combos from his range.

He either has the Royal flush or he has no flush at all, as its extremely unlikely he shows up here with any other heart. He certainly isnt calling my flop raise with 9d9h for example. Villian is also starting to look uneasy with the board runout. Hero decides there arent enough combos in villians range containing the Qh for him to call greater than 35% of the time. and stuffs $340 all in to $640 on the river.

340:640 ~ 35%

Against a better villian capable of hand reading hero probably wouldnt try this bluff, since hero actually reps pretty thin as well (royal flush or nothing lawl) but against a fish that isnt thinking about my range, he either calls with the nuts or folds.

Whole hand is kinda spew.

At what point did you interpret a loose passive raising preflop then c-betting into 5 other people as weak? You ranged him on broadways, but then c/r a flop that smacks his range??

I feel like your description of yourself is trying to justify your play.

What hands do you think V b/f's otf, or what turn cards are scary for his b/c range? You don't really consider ranges until after the flop.

Depends if V can think at all otr, you can only really have AxQh or Qhxh, and the combos of those are kinda cut down as you arent c/r flop everytime (esp with gutter) and are probably c-betting the turn with TP + RFD and c-betting turn with a flush.
QhTx is c-betting turn, hitting broadway with the nut flush redraw is never checking turn.

Your Qxhh hands are cut down as you probably don't call with all that many non broadway kickers preflop.

Depends if fish can think about this, probably not. What he does think though is that his big two pair/set/straight is a big enough hand that he can't possibly lay it down given all that money out there. "If you got it you got it."

fwiw I don't think this is a good bluff against ANYONE

You can tell you're making a bad bluff when you decide on the turn he's never folding, then bluff the river because you think he's going to fold. If he folded, congrats.

I interpreted his cbet as weak when he bets $40 into $120. Looks alot like AJ QQ TT AQ possibly AT QJ 99. I think if he has he K or better, he almost certainly bets more.

Villian is not capable of thinking of ranges, like i said at the end of my post, i wouldnt be bluffing a better player capable of hand reading since i rep very thin.

Venice, i generally agree with you that changing the plan midway through a hand is generally a bad idea, but there are cards that can completely change the complexion of the board, and therefore change the way the hand should be played. Hes unlikely to fold the turn because he picks up two pair, and or straights. On the river we need at least 35% of his range to fold to show a profit. I think he likely folds close to 50% if not more on the river.

I too think whole hand is kinda spew.

Although I am all for the pre-flop call, and alot of folks here only responses are fold pre.

The flop is a clear fold. If you are gonna bluff I think your sizing is way to large. I believe you could accomplish the sane purpose for much less. $160-180 is more than enough.

The turn is obviously check/fold.

River brings ultimate bluff card. Your bluff sizing is ideal.

He only needs to fold 35% to make your play +ev, but there is no way he is folding 35% of his flop calling range to 1/2 pot size bet. He is calling all Q's and hero calling 2+ pair. (Fish don't fold 2 pair). I honestly can't come up with 1 hand he calls flop and folds river if he is truly fishy.

I've seen V show up with 1 pair here. Cause pot was just to big.

Bright side is your getting paid off the rest of the night!!!!!!!

Hope it worked out for you.

I don't really like bluffing with showdown value. Your flop raise is bad imo. When the first aggressor gets a call I doubt your bluff raise is ever getting through both players.

I felt that villian would fold most of his two pairs and even straights. If hes folding most of his two pairs and straights that more then comprises 35% of his range. Obv some fish will call off two pair or even one pair here cus pot so big lol! But its worth noting that even though this v was a fish, he was also running good and not on tilt. I felt he was capable of making a laydown in this spot.

you had to jam the turn if you wanted to bluff him out. A very good card for you. straight, flush, everything got there. checking turn and bombing river is total spazz.

The person in question who called in mp was a solid player who i knew would be very unlikely to call my raise. It wasnt a question of getting through him, but rather the preflop raiser. Are you never turning made hands into bluffs then? Calling the flop here oop is pretty bad. Its either fold or raise.

I listed my reasons in op for not jamming turn. I think its a very clear check fold on turn and it isnt even close. A low club would be the best turn barrel card imo