Poker prop-betting with Phil Gordon

LAS VEGAS – The second session of Round 1 matches at the NBC Heads-Up Poker Championship was set to begin Friday afternoon and the Caesars Palace poker room-turned-TV-studio was at capacity. Except for the chair directly to my right up on press row.

Little did I know that this vacant seat was about to cost me some of my sacred Las Vegas bankroll.

As the NBC crew began to holler "clear the set," I noticed poker pro Phil Gordon at the room's entrance waving me down, asking if the empty seat was taken. I shook my head "No" and Gordon and his 6-foot-8 frame began to uncomfortably make his way through the crowd to claim the last open seat in the house.

Phil Gordon is looking pretty confident as he gets ready for this first-round match with Tom Dwan in the NBC Heads-Up Poker Championship at Caesars Palace in Las Vegas on Friday. (photo by Gary Trask)

Shortly after the 39-year-old Gordon took his seat, Heads-Up TV hostess Leeann Tweeden did her intro for the cameras and then the cards were in the air. Seconds later, Gordon – whose first-round match in the event was scheduled for later on in the third session – asked me whom I liked to win the Annie Duke-Andy Bloch match that was being played directly in front of us.

"I like Bloch," I said. "You math guys always seem to do well here."

"Yeah, I like Andy too," Gordon said. "But if you give me 8-to-5 odds on Annie, I'll take it. I'm looking for some action."

If you know anything about me, you won't be surprised to hear that I was more than up for having some "interest" on the matches. But I also wasn't going to be bullied. Phil Gordon has nearly $2 million in career earnings, mountains and mountains more cash than yours truly has ever come close to winning when it comes to gambling. But, even still, I didn't just fall off a turnip truck outside on the Las Vegas Strip.

Or so I thought.

"No way," I shot back without hesitation. "This is a 6-to-5 match, at best."

"OK, I'll take Annie as the 6-to-5 dog," Gordon said as I nodded in agreement. We settled on a figure that was much less than Gordon wanted to put on the line and it was "Go time."

About three minutes later, Gordon came back at me again.

"Who do you like in the featured table?" he said as he motioned to the Antonio Esfandiari-Sammy Farha match that was going on at center stage.

"That's a tough one," I said, suddenly feeling like Mike Sexton on a WPT telecast. "But, in my (Heads-Up) preview I picked Antonio to get to the Final Four, so I have to like him here."

"OK, give me Sammy as a 6-to-5 dog," Gordon said to me without looking up.

"Alright," I said hesitantly, feeling as if there was some sort of set-up going on with me as the perfect foil. "You're on."

Within the next 20 minutes, things began to look bleak for the two guys I decided to back. Duke doubled up Bloch and Farha was slowly draining The Magician. When Esfandiari's stack got even lower, Gordon looked at me and giggled like a little schoolgirl.

"Looks like I'll be free-rolling pretty soon," he taunted me.

Just as I started to get worried about Esfandiari blowing both my bet with Gordon and my Final Four pick, I heard an all-in call from the Duke-Bloch match. Bloch was at risk and when Duke sucked out on the river, I was officially 0-for-1 against Gordon.

Like a shark sensing blood in the water, Gordon asked me who else I had in my Final Four.

"Eastgate, 'durrr' Dwan and Eli Elezra," I said with a little less confidence in my voice.

As soon as the words came out of my mouth, Gordon shot me a curious look. Then I quickly remembered that Gordon's first-round opponent was Dwan.

"It's going to be pretty tough for Dwan to make the Final Four because he's not even going to get out of the first round," Gordon said with a hearty laugh.

"What do you make the odds on that match?" I inquired.

"Oh, I'm like a 9-to-5 underdog," Gordon tried to say convincingly. "Nobody's giving me a shot. But I am going to win."

"I like your confidence," I said. "You got a strategy?"

"Well, I figure that with the 15-minute levels there are typically about 10 or 12 hands per level," Gordon explained. "I'm going to try and slow it down just a bit, maybe get it to like ten hands a level. He's definitely a better player than me, but I'm the better math guy. If I can somehow survive until the blinds get big, I can beat him."

"What makes 'durrr' so good?" I asked.

"He's incredibly aggressive and he's fearless," Gordon said. "That makes him tough to beat."

Just as Gordon was wrapping up his strategy session with me, a severely short-stacked Esfandiari got a call on an all-in and reluctantly turned over an Ace-Eight unsuited with a roll of his eyes. He got no help from the turn or the river and just like that I was 0-for-2.

Gordon immediately turned to me with his hand held open and an ear-to-ear smile splashed across his face. I reached into my pocket to hand over the cash when he suddenly pulled back.

"Let's go double or nothing on my match," he said without giving me much of a choice. "I'll take myself as a 6-to-5 dog. OK?"

Phil Gordon conducts his post-match interview after quickly disposing of Tom Dwan in the first round of the NBC Heads-Up Poker Championship on Friday. (photo by Gary Trask)

We shook on the bet and I wished him luck as he walked away to get ready for his match.

After dinner break, the day's third session got underway and it didn't take long for Gordon to successfully hatch his plan. For a guy looking to "slow things down," Gordon made quick work of Dwan, eliminating him in about 40 minutes.

On the final hand, Gordon – holding pocket sevens – three-bet and Dwan went all-in with Ace-King off suit. Gordon called and Dwan's desperate plea for a "one-time" didn't come through. My beat down at the hands of Gordon continued.

Gordon -- who improved to 3-2 in his Heads-Up career and moved on to Saturday's second round where he would face Phil Laak -- stood up and shook hands with Dwan and then turned to the nearby crowd to receive congratulations. Before making his way over to conduct a post-match interview with Tweeden for the NBC cameras, Gordon's next order of business was to come and collect. As he started to make his way over to my side of the room, I quickly fumbled to get my cash together, but before I could lean over the table and hand over the green to Gordon, he stopped me short.

"Hold on to it and make a donation to PreventCancer.org," he said to me so everyone in the vicinity could hear about our bet.

"Don't forget," he said a little louder, with the point of a finger as he walked away. "You better do it!"

"Consider it done, Phil" I said sheepishly, before having to explain to everyone around me what had just transpired.

It turns out the woman who taught Gordon how play poker – Elizabeth Lucas from South Carolina – lost a battle with cancer back in 2004 on the same day he won his first World Poker Tour title. It goes without saying that the fight to beat the dreaded disease is near and dear to Gordon's heart.

A few hours later when my day of watching nearly 12 hours of poker was over, I logged onto PreventCancer.org and made my donation, putting it in memory of Elizabeth Lucas. And so Gordon wouldn't try and hunt me down, I e-mailed him the receipt.

Just before I shut down my computer for the night, I received an e-mail reply from Gordon.

"Well played, sir!" it read. "Want to bet a match tomorrow?"

Somehow I had the feeling Gordon wasn't kidding. But I politely declined. I know when I'm beat and I don't chase my losses. But if every bet I had to pay off felt as good as this one, I'd happily up the ante on all of my wagers.

Believe me, losing money has never felt so rewarding.