I'm in a local $1-$1 FR cash game when this hand occurs. I've played with Villian many times and have him pegged as the loose, passive type. All other players fall into this category as well.

Previous reads from this session on Villian:
1)Opened UTG for 16BB with 77 (showed when no one called)
2)Painfully called AI 4 bet pre-flop with KK against nit opponent

Now for the hand:

Villian UTG +1 with ~200BB
Hero in the CO with ~160BB (Hero is dealt 99)

SB posts $1
BB posts $1
UTG folds
Villan raises to $18
UTG +2 folds
UTG +3 calls $18
HJ folds
Hero is in the CO with 99 and shoves AI for $160
Button folds
SB folds
BB folds
Villian.......

Based on the previous actions of the Villian, is this an OK shove, or is my play too rash? I'm basically bluffing here I believe, not expecting value call from weaker hands, but more leaning towards possible 1010-QQ AK type hands folding. Is 99 too weak of a hand to apply this pressure with?

*Sidenote - UTG +3's call is not especially suspicious, I've played with him for 2+ hrs and haven't seen any slow play tendencies..

Sure, why not?

In a vacuum it's not horrible, but let's just play TT+ here and not trivial shove 9's

Extremely risky play, since you are never in good shape if called.

This is you...

Eh, when it gets called it's always by a bigger pair or AKs, but this will result in a fold a lot of the time and a nice uncontested pot - it's not that bad.

Do you know what he would open for if he held a premium? This probably can be solved mathematically, but something is telling me your overshove isn't a very good play. It seems like you are putting way too much money at risk on a bluff. I'm not sure.

Well in the hand where he hesitated to call off with KK pre, the pot was opened to $6 and he re-raised to $20. His normal opens are between $4-$6. The only reason I felt the shove was an option was due to the unusual open for $16 earlier in the night with 77. I assumed this was his way of taking down the pot without having to play a tricky middle pair post flop.

With that info, snap fold pre

Would UTG+3 flat the open raise with TT-JJ? If V folds, would UTG+3 call your shove with TT-JJ? Have you made this play before during this session? What is your goal by going all-in? Is it to just fold out TT-QQ and AK?

If I was observing the game at the table, I would put you on exactly what you have, a medium pair that doesn't want to play post flop. Would your shove here with QQ+?

This game is mainly older generation players who fear aggression and play their two cards only. My goal in shoving was what I felt like would be a high probability of better hands folding to scoop the $38 pot (anything less than AA or KK, and more times than not AK as well).
I 1: put the initial raiser on a mid pair due to his previous action with the 77 in a similar spot
2: felt I was getting a fold from anything but the TOP of opponent's range, due to the unwillingness to put it in the middle without utmost certainty of having the nuts

This game typically views shoves as a level 1 strength play, not a defensive one.

Shove is completely unneccessary. Could probably get the job done with 40+ if you wanted to play risky but risking 160bb preflop like this isn't even a good play with JJ. Assuming UTG+3 has anywher around 100bb you could call and set mine but folding works too.

Personally I do not like making reads based on the history of how he played one hand before but it seems you have played before so you may know more about him.

Sometimes based on table flow and my image, I like the shove vs someone who is tilting or who raises big with a wider range. It seems too thin/guessy/risky unless you know more or want to create a maniac image.

In this instance I would prefer to fold pre or outplay this player post flop. Knowing his flop c-betting tendencies would help. You get more value when/if he c-bets with weaker hands or hands you can get him to fold.

Some flops will be scary to see such as KQx or Axx, so being able to know when to apply pressure is important. If you have a tight image yourself it will make it easier to take down.

I don't like shoving at all. Given the way you've described the opponents (loose passive) I prefer a call. You have position and can probably safely take the pot away on the flop if checked to even if over cards come. If one or both villains bets out on the flop, you can safely fold. I generally prefer aggression though so if you do want to 3bet squeeze, why not make it like $60-$70. That should get the same benefit of potentially folding out 1010-QQ and if villain shoves you can fold. By shoving, you are folding ensuring only better hands call plus possibly AK.

OP, r u shoving here with AA, KK etc...?

Assuming an opening range of 77+,ATs+,KQs,AQo+ and a calling range of QQ+,AKs,AKo:
62% you take down the pot uncontested for +$38.
38% you get all in with 35% equity for -$38.
This looks like a net positive play of $9 if neither villain ever calls with TT or JJ, which will not be the case when you get caught making this play a couple times.

I think raising to $45 gets the folds almost as much as a shove, but also lets you get away from the bigger hands 4bets. It is also easier to balance your play.

IMO 3 betting all in is putting you in a spot where you are crushed a majority of the time and a coin flip the rest of the time.

Do you think you could get the same range of hands that you want to fold with a 3 bet of $40-50? Wouldn't that leave you with the ability to call/fold to a 4 bet shove?

I really appreciate everyone's input on the hand.

I guess because I know how the hand turned out (UTG +1 insta folded, and UTG +3 proclaimed 'you know I fold!', and UTG +1 showed QQ, saying how he didn't want to flip for his chips) I'm shove biased, but after reading the comments I agree that in usual cases a re-raise to $60-$70 may have been a better play. However, in this particular instance the $70 almost certainly sees a flop with the QQ.