There's a regularly who plays in my 2/5 underground game. He's a 60-ish man who's gambled his whole life but isn't terribly good at poker, although he's much better than the most of the rest of this group. The money at these stakes doesn't mean much to him. He could win or lose $2k in a session and it wouldn't bother him at all. Poker-wise he's very LAG preflop (except he rarely 3-bets light), but is fairly good at assessing ranges and plays semi-decent post-flop, although he tends to be take passive lines a lot and probably calls too much overall.

I play a mostly TAG style with some limping of speculative hands IP, but people think I'm much looser than I actually am. I call a lot until I can beat top pair then I value bet the &^*& out of it and I get paid like a pimp. Sometimes I get to showdown with some surprising hands (2-4s is a famous one, won a huge pot w/it), and I've been called the luckiest SOB that ever played there. Last week I coolered 3 other players in a multi-way pot with the over boat vs. under boat vs. trips w/TK vs nut straight. I regularly cash out for multiple buy-ins. Not trying to brag, just describing my image.

When we get in a hand, he likes to trap me. Last night he checked a flush to me OTR after I'd fired 80% PSBs at the flop and turn w/TP. He also likes to call me down super light. He'll limp-call a raise with Q5s, flop a 5, and go to the river with it if I'm doing the betting.

He likes to raise preflop with a very loose range in position. I've seen him raise as light as 78o+, 22+, 68s+. He's also the type to straddle to $50 on his first hand - he does like the gamble. There is almost no light 3-betting at this game and most of the players are super stations. I've 3-bet to $100 and gotten 3 callers from players with hands like KJo and 44. When I've 3-bet this player's opens in the past, he called 100% of the time even OOP and (I think) mostly played fit or fold post-flop in those bigger pots, although the sample size is lacking there. He doesn't like to steal OOP as much but as I said he loves to trap me and call down light so bluffing can sometimes be expensive.

There are also several players who love to limp-shove their monsters so light 3-betting can be a somewhat dangerous proposition.

How should I handle this kind of player? 3-bet more light? Play as many hands in position against him? Value town him to death? I feel like there's a way I could be winning a lot more money off him.

Value bet when you have it. Check when you don't.

EZ game.

Against a loose/passive player, value bet more often, bluff less often. You can expand your own calling range preflop too (especially in position) but it seems like you're already doing that.

Just my opinion...

Love how you first call the guy not very good...

...then go on to describe what is a decent LAG who you are having trouble with.

Methinks you are your problem. Might want to get that ego under control.