How do you get max value from this ?

Setting:

Effective stacks : 700$

Villain 1 : A poker buddy of mine. Good Tag reg. Plays fairly straight forward preflop but is capable of big bluffs postflop from time to time. Respects my game and sees me as a TAG who is capable of making moves from time to time. He knows I can put pressure preflop if I see the correct opportunity with less than premium hands. He is capable of folding big hands preflop including KK vs. the right opponent. He is to my immediate left.

Previous hand, a utg reg (actually utg +2 but there was a double strattle) limps. This reg (villain 2) is probably break even, can be quite aggro generally and spewy at time. I fold a couple of callers. He ends up losing the hand without investing more than 20$ with AQ. Saying he was planning to limp and shove any raise as he only had $275.

I have been playing pretty tight on this particular table because there are 2 calling stations. So right after the hand mentioned above, be and villain 2 are talking about his limp which I was kinda puzzled about since there was a double straddle, as we are talking the following happens : Straddle pot. Villain 2 limps again UTG , UTG +1 folds. I find it odd now because villain one has limped back to back and we were just chatting about it. But I still raise to 50$ with KK (Fairly std raise since the 2 calling stations behind me). Villain 1 3bets to 160$ total , everyone folds back to me. His range is pretty strong here due to the position and the fact that he’s generally tight pre. He probably has JJ+, AK. I think AQ is out of the question here.

At this point, I’m really not sure what to do. I’m fairly early position. I find if I 4bet, alarm bells will be going on in his head. He knows I can make moves at times, but he also knows I perceive him as tight and am unlikely to make a move when he 3bets me with so many people left to act behind. What also complicates things is the god damn straddle which make the stacks shallower. I’m thinking here if I 4bet, I might as well just shove as he might perceive this as AK, possibly JJ. I might get a call from JJ and QQ if I 4bet shove due to the shallowness of stacks. If I min 4bet, or close to it, I would probably guarantee myself a call from all of his range. If I call his 3bet, I can surely pick up at least one bet post flop.

Pot is 330$ . After thinking for a while I decide to call. Flop is JJ3. I check and he bets $140. At this point, I figure there is quite a bit in the pot so I decide to just shove and pick it up there. I’m not sure exactly why I shoved cuz I honestly probably only get called with QQ at this point that I beat. He calls with JJ obviously, AA and folds AK.

I don’t know, it’s just a really weird hand. What do you guys think ? How do you max your profit/minimize your loss against this type of player in this spot ? TBH, during the hand, I really didn’t know what to do.

Flop shove is terrible as how you described him. Even though it looks like a bluff I'm sure he knows you wont do this vs him with air.

If I have a history of 4b ing light V1 I'm def. going to 4b. If not i'm calling here. If I am 100% sure he is going to cbet I lead weak to induce or when called bet turn/ shove river on non aces. (Iam assuming this is a thinking player or else no way Im doing this) Listen man no matter what my goal is to get it in here vs his range. Flop you fold out most of his hands which is not our goal. he is capable of running big bluffs? Lead weak induce a spazz shove or check/call re-evaluate turn on how to get max value.

But given you are ep and he 3b, you calling is kinda strong too. So after cbet I think he closes action if he has any sdv

This is just my pov, my two cents. Take it or leave it.

Appreciate it. It was so hard to play. I think anything i do pre at this point looks super strong to him. I actually like the weak lead. Its probably the only way i might get more out of him there.

We dont really have a 4bet history. We tend to stay out of each others way