What are your opinions on jamming into whales who show interest in pot on drawy board? Specifically the following scenario.

Whale is 65/2, and has overplayed a weak draw at least once or twice. Definitely the aggressive type.

Now I understand I crush whales' turn bet range here, but does his call jam range tighten up? Can an expert whale hunter answer this?

Also is my line good? I am the only one in the hand with <55 vpip over 40+ hands.

weak squeeze. just for that you lose a lot of your equity against 4villains, from turn check/call, check/call river too, (well on the river depend on size and card) but check raising the tun you only get call from 2pair or better sometimes AA.

Bet more on flop. Raise turn, but don't jam!

Yeah bet more flop.
I think this is an interesting line, def not standard but might be the best play given your read.
Your line looks drawy so I would feel confident your jam is +ev against this whale.

-The turn is hard spot given that there are 4 people in the hand and the flop hits a lot of their ranges
-Checking seems grand to me
-When the whale that you have a read on bets and everyone else in the pot gets out of the way I think raising is the best play.
-Maybe raising to $4.5 (giving him the chance to bluff) would be more +ev though

Interested to know what other people think, even though the play is not standard he has a very relevant read on the villain:

"Whale is 65/2, and has overplayed a weak draw at least once or twice. Definitely the aggressive type. " With players like this I am looking for an excuse to get it in the middle