Phil Ivey’s Caddie for the Day
I was just a twenty-year-old college kid home for the summer having fun at the golf course. I was on the putting green at TPC Summerlin when I saw a cart approach that seemed to slow down.
“Hey, you won the Men’s Club Championship last year right?”
I nodded my head.
“Cool, do you want to caddy for me in this match today?”
Excited and nervous, I gave him a thumbs-up and hopped into his cart. I knew the next few hours caddying for Phil Ivey was going to be something I would never forget.
When Did This Happen?
August 2007. I was about to start my third year at San Diego State University. At the time, I was a member at TPC Summerlin and was out practicing on a hot summer day. As a college golfer, this was very typical for me at the time.
Who Else Played in the Match?
If you were a poker player or fan of the game like myself ten years ago, then these names will certainly ring a bell. Phil was playing two separate matches: one against Doyle Brunson and one against Mike Sexton. Chip Reese and Eric Lindgren rounded out the star-studded five-some.
Understand the Context of the Era
Let’s just be honest. This was 2007, and these guys were flushed with cash. Full Tilt Poker was booming, and Phil and Eric were “Team Full Tilt players”. At the time, these $10,000 per hole matches Phil had going were just a regular day for these guys.
Understand the Context of Myself
At the time, I was just starting to play a lot of poker. I was still a few weeks away from turning twenty-one, but our home golf course at San Diego State University was an on an Indian Reservation where you only had to be 18 to gamble. Most days after practice at Barona Creek Golf Club, I went into the casino and played poker. I was watching a lot of poker on television, and needless to say, I was a huge fan of these guys, especially Phil.
A Bad Start to the Match
Phil’s instructions to me were clear. He wanted me to tell him the yardages, make sure he was always lined up correctly and help him read the putts. I was so honored to do this I could barely contain my excitement.
Unfortunately, by the third hole, my sense of enjoyment was beginning to fade. Phil got off to such a bad start I began to worry if he would blame me. He lost the first two holes to Doyle and Mike, and before I could blink he was down $40,000.
The cart girl drove up and Phil asked for a Gatorade. He handed her a $100 bill and told her to keep the change. I thought to myself, “he must not be that pissed yet if he is tipping the girl $97.50!”
It was now the 4th hole and I saw the starter driving towards our group. The starter is the person who is responsible for getting the golfers teed off, and controlling the pace of play for the course. I knew 5-somes were not allowed, as four players was the maximum that TPC allowed per group. I assumed he was going to question Phil and the guys and possibly tell them to break into two separate groups. Boy was I wrong.
He nearly begged the guys to go get them whatever food or drinks they needed for the rest of the round. He also handed them all wet washcloths to rinse their faces off, as everyone was dripping in sweat. Then it all made sense. When you are tipping $97.50…If I was an employee, I’d be jumping through hoops to go overboard as well.
The Putt on the 8th Hole
The first seven holes were not good for Phil. He was playing poorly and losing nearly every hole. He started doubling his bets to try and get back to even. Phil was now losing well into the six figures.
Both Mike and Doyle had made a four on the par three 8th hole. Phil had a 25-foot uphill putt for par that would win him the hole if he could somehow make it. Asking me what I thought I confidently showed him where to aim. It was a tough putt. I was just hoping he could 2-putt and tie the hole. To my surprise, he drained it! I felt so happy and relieved knowing he trusted what I told him and it worked out.
What Happened Next?
Again, the pure joy quickly vanished. Phil tugged his tee shot out of bounds on the 9th tee box and went on to lose the hole. The 10th hole was no better. After Doyle and Mike’s win on the 10th hole, Phil’s frustration finally started to set in.
A few curse words later, Phil was fired up. The out of bounds tee shot on the 11th hole was the final straw. Getting into the cart he calmly said, “Drive us in to the clubhouse.” He exchanged a few words with the guys in the group about settling up the money later. These guys were playing so often with each other at the time that this was ordinary. Frankly, they each won and lost back and forth so much that the money just went around in a big circle.
As I was flooring the pedal trying to get Phil where he wanted go, I could not help but think to myself, “Is he going to tip me?” It was only 10 in a half holes. Surely I would never ask, as the experience by itself was worth more than whatever a caddie normally gets paid.
This next moment is the single moment I remember most about that day. As we pull up towards the clubhouse I see a stunning, burgundy Rolls Royce parked right in the front. There was an extremely large male holding the door to the back seat open. Phil reaches for his wallet and hands me $500 so casually, you would think it was $3 and I was a valet driver. He gets in the back seat and the man grabs his clubs and sticks them in the trunk. Off they went.
I sort of sat there for a minute in awe. Not because he just tipped me $500, but because of the whole experience in itself. It was then I realized how normal of a day this was for Phil. This guy lost over $100,000 in two hours and hardly batted an eye.
I ended up playing professional poker for 6 years after college, and I can’t help but think this experience played a part. I never expected to be playing the highest stakes of poker, let alone betting $10,000 per hole in golf like he was. But the dream was there. Being able to do something that allowed me the freedom these guys seemed to have was something I craved for a long time.
I have been fortunate enough to run into Phil several more times over the years, but have not had the chance to caddie for him again. Well, not yet at least!