Stud Eight-or-Better for $500,000

In my last column, I shared a couple of hands with you from the challenge matches that I play at Wynn Las Vegas. Barry Greenstein has agreed to play me in every form of poker that I listed for challenge matches: limit hold'em, stud, Omaha eight-or-better, stud eight-or-better, deuce-to-seven triple draw, ace-to-five triple draw, pot-limit Omaha, pot-limit hold'em, and no-limit hold'em.

We'd already played a match and a rematch in seven-card stud, as well as a match in pot-limit Omaha. I lost both stud matches but came back with a win in pot-limit Omaha, so I was down 2-1 in the series.

Barry gets to choose the games he wants to play and their order, so the next game on his list was stud eight-or-better.

As I did in pot-limit Omaha, I got off to a great start and took a big lead, winning almost $300,000 in the first hour! That's an astronomical amount of money to win in such a short amount of time, playing $4,000-$8,000 stud eight-or-better.

Over the next 12 hours of play, I was always floating around the $300,000 mark – up as much as $360,000 and as little as $200,000. There was one particular hand that had me shaking my head:

With a $1,000 ante and a $1,000 bring-in, I brought it in with the 2. Barry made it $4,000 to go with the J. I then looked down at my holecards and found the A 3. That's a pretty strong starting hand in stud eight-or-better, so I decided to reraise Barry to $8,000. He called. On fourth street, our boards looked like this:

Barry: (X-X) J 3

Me: (A3) 2 5

Barry checked, and I made what is an automatic bet in this situation. Barry called, which immediately led me to believe that he must have a high pair, most likely the jacks. On fifth street, our boards were as follows:

Barry: (X-X) J 3 A

Me: (A 3) 2 5 10

Now, while the 10 didn't improve my low, it did give me a flush draw to go along with my low draw and straight draw. Even if Barry showed me a pair of jacks, I'd still be more than a 2-1 favorite on fifth street. In fact, even if Barry had a hand like jacks and threes, I'd still be more than a 3-2 favorite! Barry checked once again, and, obviously, I bet my superdraw.

On sixth street, our boards were:

Barry: (X-X) J 3 A 9

Me: (A 3) 2 5 10 10

Once again, even though it seemed clear that my pair of tens wasn't in the lead, my pair in combination with my strong draw made me almost a 2-1 favorite over a pair of jacks. If, however, Barry had already made two pair with a hand like jacks and threes, his hand would be a 51 percent to 49 percent favorite.

Now, when I'm thinking through a hand, do I know these precise numbers? No, of course not, but I do have a rough idea – enough of an idea to know that it was safe to bet out on sixth street with my hand.

To my surprise, Barry raised me! This play seemed rather bizarre to me, considering the fact that I reraised Barry on third street and bet the hand hard all the way. I could have a made flush, aces and tens, or even a full house.

Barry's raise seemed suspect to me, so knowing thatI couldn't possibly be a big underdog against any of Barry's possible holdings, I reraised!

Barry thought about it for some time, which made me feel great about my decision to reraise. If all Barry had when he raised me was a pair of jacks, my hand would be the favorite.

One thing I didn't see as a legitimate possibility was Barry folding to a reraise. It was possible, of course, but it didn't seem realistic – that is, until he folded! Wow, Barry calling me on sixth street wouldn't have been a disaster, but winning this sizeable pot without even having to improve was a great result for me.

I never got to see Barry's hand, but could only logically assume that he had a pair of jacks and thought that since I reraised, I could beat that, and he may be drawing dead.

That hand helped kick-start a nice little rush, and after 17 total hours of play, I finally beat Barry and evened our series at 2-2.

Stud eight-or-better has always been one of my favorite games, because of its subtle complexities. One of the keys to being a successful stud eight-or-better player is knowing when you have a small edge and maximizing it. Since there are so many unique situations in that game, I've probably done more computer simulations on it than any other. There are many situations in the game when what appears to be the best hand is actually a statistical underdog.

Did you know that even a lowly pair of deuces and a low draw on fifth street is better than an 11-10 favorite over a pair of kings? I know that because I just did my homework and ran the hands on my computer. That's food for thought.