The $5 Million Challenge Continues -A $500,000 challenge match against Barry Greenstein

Before the World Series of Poker started, Barry Greenstein had agreed to play me in all the nine forms of poker that I had listed in my open challenge. Since I asked for a rematch in seven-card stud after he beat me, the amount of money that each of us would be risking in these matches was $5 million.

My rematch in seven-card stud was about as bad as the first match, and I found myself down 0-2 and $1 million. That's not exactly what I had planned when I asked for a rematch!

The next game that Barry chose from the list was pot-limit Omaha (PLO). Now, I didn't have very much heads-up PLO experience going into this match, so I did a little research on the game. I ran some simulations on my computer and also talked to some excellent PLO players about some of the subtleties of the game.

Right off the bat, I seized the lead and had Barry all in within the first hour of play! He won that pot and two other monster all-in pots, but I still maintained the lead when the following hand came down:

With the blinds at $1,000-$2,000, I called Barry's $6,000 button raise with K-J-9-8. The flop came Q-10-4 rainbow and I checked to Barry. He bet $10,000, just as he did every time he raised before the flop, and I decided to make it $40,000 to go.

When Barry reraised me another $80,000, I wasn't happy about it, but thought I should call to see if I could hit my straight on the turn.

The turn card was a king, filling my straight, but I checked, nonetheless. Barry then went all in, betting more than a quarter of a million dollars. After much deliberation, I finally decided to fold my hand, giving Barry credit for having A-J for the nut straight.

Now, that's not the interesting hand that I wanted to share with you, but it sets up the following hand that came much later:

I raised from the button to $6,000 with J 4 8-5. Barry reraised the pot to $18,000. Generally, that's not a very good play when heads up, since position is so important. Of course, if your hand is strong enough, there is nothing wrong with it as long as you proceed cautiously after the flop.

The flop came 9 7 6 and Barry bet $25,000. This was in line with what he had been doing throughout the match. When he had raised before the flop from the button, he would bet $10,000 when checked to, and when he had reraised from out of position, he would fire out $25,000 at every flop, whether he had something or not.

With the dummy end of the straight, I decided to play cautiously by just calling. The turn was the J, putting a backdoor-flush possibility on the board. Barry checked and I decided to make a relatively weak-looking bet of $40,000.

Barry thought about it for a while and then finally decided to raise me another $170,000! Yikes, it was decision time for me. The last time I was facing a similar situation with the second nuts, I folded, but this situation felt slightly different.

Based on my memory of past hands that we'd played, I just didn't think Barry had the 10-8 combination in his hand.

Instead, it seemed to me that he had either top set or a hand like K-Q-10 with a diamond draw. With a hand like that,

Barry may have decided to play it fast since even if I had a straight, he'd still have a ton of outs.

What complicated my decision further was that I was doing a good job of winning the smaller pots that were less risky. If I lost this pot, I'd be giving up the lead to Barry, while folding would have us sitting close to even.

Ultimately, I went with my read, though, and raised Barry his last $108,000, for a pot of $722,000. The river was the beautiful 3 and Barry shook his head in disbelief. I was on the board, down 2-1 in our challenge match series, not to mention $500,000.

I never saw Barry's hand, but it doesn't really matter whether or not he had the set or the draw. My read of this particular situation was that he didn't have the nuts.

It all boiled down to instinct. In two similar situations with the second-nut straight, my final decision was based on some game theory, but mostly it was based on pure instinct.

In my next column, I'll again discuss a hand from my heads-up duels with Barry Greenstein, but we'll be looking at a stud eight-or-better hand.

Read Daniel's daily blog at his website www.fullcontactpoker.com.