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How well did I play this poker hand?

The game is $1-2 No Limit Hold'em. I start in the big blind of $2 with $160. My hand is 8, 5 unsuited. There are four callers for $2 and I check my option to raise. The flop is J, 8, 5. I bet $10 and am raised by a solid player to $25. He has me covered by over $100. A loose newbie player who is stuck $800 in the game calls $25. I re-raise to $60 and both players call The turn card is a 3. I go all-in for $100. The solid player thinks awhile and calls. The loose player also calls. The river is a nine. The solid player bets and the loose player folds. He shows 6,7 for a straight. After the hand, I say that I did not raise enough on the flop to chase him out. He says that he likes to play the same way I did and get his money in good because he was a 4 to 1 underdog. He says he called also because he could see the loose player was going to call also, giving him better odds for the call.

Public Comments

1. I wouldn't have done anything more than check or fold with an 8-5 offsuit. Two pair (especially two low pair like yours) is a weak hand to go all-in. ESPECIALLY with a higher card showing. someone with a J-5 or J-8 would have had a better 2-pair hand after the flop. After the turn, your mistake was going all in. Someone could have beaten you badly with the straight (like they did), or a pair of pocket 3's, 5's, or 8's for a three of a kind, or could have had an 8-9 and beaten you with the higher pair, etc. Live an learn.... better luck next time, hope you can turn this into a learning experience and be a better player.
2. It's one of those unfortunate situations that happens in poker. You are already in the hand by virtue of the fact that you are in the big blind. Your useless hand seems to turn to gold when you flop two pair. Two pair is often the best hand. It is hard to put your opponent on J5 or J8, because these are useless holdings and few players are going to play these hands unless they are idiots (or very good players who know exactly what they are doing). But it is entirely possible that a player has 67 (often played when suited), JJ, 88 or 55. In which case they have an open ended straight draw, or they flopped a set. You bet out roughly a pot sized bet, and you get raised and then the raise is called. This is not a good sign. The raise could be just a play against a continuation bet, but a call of that raise, even by a donkey is generally not good. I don't like your re-raise at all. Both players have already shown a willingness to stay even in the face of a bet, raise and call. So it doesn't seem like they are going away. Sure enough, they both call. Even though the turn seems like a safe card to you, it would concern me to move all in here given the clear desire shown by your opponents to keep calling all this time. Sure they could be drawing, as indeed we know one of them was, but equally trips is still not out of the question. You have made a bet, and a re-raise already and you still could not shake the two opponents. In some cases maybe an all in move would finally get rid of them, but I don't see both players folding to a bet here. They seem to have become entrenched in their hands, despite the poor pot odds the eventual winner was getting after the turn. Sure enough your bet is called by both players and the river seals your fate. While the books talk about aggression, the problem here is that even with your aggression you were meeting with a massive amount of stubborn resistance. By the way this hand was played, I don't think you were getting those two opponents off their hand. Therefore the all in move put you at unnecessary risk. Having said that however, if everyone had checked the turn, the guy who eventually made the straight would have probably value bet it, and you probably would have called. But you might have extricated yourself with some of your stack remaining.
3. I know Texas hold'em is a game of terribly aggressive bets. Two pair is not great, but, looking at what was turned, not such a bad play. Straights are rare in any format of poker. I think if you are playing agianst two others, and the turn is not rich in face cards, two pair has a reasonably good chance of winning.