My Money Match With Phil

We arrived at The Farms Golf Club, the exclusive golf haven outside San Diego, parked our bags on the range and hit a couple of warmup wedges. A few shots into our session, Phil Mickelson wandered over in a snug black shirt and blinding white shorts, looking stronger than I’d imagined. He introduced himself and said because a leisurely ladies’ group was about to head out, we needed to beat them to the tee. We could hit an extra ball off the first to warm up, he added. 

Maybe we were being played, maybe we weren’t. I don’t remember us protesting, but we didn’t verify the veracity of Mickelson’s declaration. These are the advantages home field affords.  

Yes, I was about to play a match against Phil Mickleson. He was looking for some action to prepare for his season debut, and for one October day, I was the mini-tour player giving him that action. 

According to excerpts from Billy Walters’s new book, Gambler: Secrets from a Life at Risk, published by Fire Pit Collective, Mickelson lost $100 million and bet $1 billion on sports over three decades. Walters described the business relationship, lasting from 2010 to ’14, as a partnership in which the men shared the risk and reward equally. 

If Tiger Woods in his prime asked you to be his four-ball partner for a year’s worth of matches, would you risk a hefty chunk of your annual salary to do it? That’s not unlike the decision Mickelson made when he partnered with Walters, who is widely considered the greatest sports bettor of all time. If you know anything about Walters, you know he doesn’t just gamble, he also wins. 

It’s hard to imagine Mickelson losing money over the length of their partnership if he had run solely with Walters. But Walters wrote that Mickelson wasn’t. He didn’t have the discipline. Not all action is created equal, but whether it was a long-shot five-team parlay or a money game against a mini-tour player, Mickelson loved the action. 

It should be noted that in the wake of the release of the Walters book excerpt, Mickelson issued a statement in which he said he sought help for a gambling addiction in recent years and that the therapy improved his well-being.

It was an interesting time to tee it up with Phil. He had just returned from the Ryder Cup at Gleneagles. Remember that bludgeoning? The assault on the U.S. team came from both inside and out, with Mickelson ripping captain Tom Watson during an unforgettable post-match press conference. The unique timing of our match was a window into Mickelson’s fervor for competition, the lengths he was willing to go to win, and his unyielding belief that he was always right. 

How, you might wonder, did I get myself into this? Earlier in the year, I had followed a couple of sharp gambling friends to Las Vegas and found a place to hang my hat. There were plenty of games to be found around town: skins here, a Nassau there, with Wolf and Snakes in between. Prop bets were made on everything from a straightforward bunker shot to whether someone could toss a ball in the hole from off the green. Some golfers prided themselves on being the best negotiators. I tried to be on the side of the best negotiator while playing the best golf. 

My foray to Vegas was twofold: I was trying to make enough money to pursue professional golf on a full-time basis and get more comfortable playing for money. And what better time? I was 30, not yet married or the father of a toddler, as I am now. These ambitions led me to a fast-talking jewelry dealer we’ll call Sam, a big personality who loved to play for cash. He reminded me of a Goodfellas character – he always had a story, a connection and an angle. He would often talk until the moment he pulled the club back. As the ball was in the air, especially if the shot looked good, he carried on. 

Sam could be boisterous, but he was genuine, he was a generous tipper, and he loved golf. We were usually on the opposite sides of $100 bets, and I always looked forward to playing against him. It wasn’t just because I won more than I lost, though that didn’t hurt. 

Sam played frequently at a couple of clubs where Mickelson might be found. One was famous for its high-stakes money games. I met a guy who claimed to have quit gambling cold turkey after losing $1 million in one weekend at one of the clubs. Sam occasionally mentioned bringing me along for a game, or bringing Mickelson to Las Vegas. Given my friend’s penchant for exaggeration, I never gave the possibility much thought. 

Then one day in the fall of 2014, I was hitting balls when Sam called. Mickelson had been laying low after the Ryder Cup but was starting to prepare for the fall season, and he wanted to stress-test his game in a money match. Golf and gambling have long been close companions, and for professionals, playing for your own money is a way to simulate Tour pressure. The negotiations had begun: What was my risk appetite? 

“Listen, I’d love to play Phil, but I’m not going to rob a bank to do it,” I told Sam.

No problem, he said. He would set the stakes and I could take as much of the action as I wanted. If I wanted none, he’d still stake the game. We were on.  

Not long after, I was sitting in a hotel room in Southern California, trying to visualize a successful day on a golf course I’d never seen, and praying I’d bring my best game to the course the following morning. 

The matches would take place inside a fivesome. I had two games, with Sam as my partner in one and a friend of Sam’s as my partner in another – each against Mickelson and his partner. Mickelson and I also would play a heads-up match for a set amount with the option to press for half that amount once either of us had won. 

We were supposed to play at The Bridges, a private club in Rancho Santa Fe, but Mickelson’s partner for the day, an attorney from Orange County, moved the game at the last minute to The Farms. The reason: The Bridges had recently aerated its greens. Who knows if that was true? Was it just more gamesmanship?

“I’m not going to play Phil for the experience,” Sam said on the way to the course. “This isn’t tourism.” I wasn’t sure I could say the same. That conversation and the ones that followed linger in my mind.  

After too much time in morning rush-hour traffic, we arrived at The Farms and made our way to the range. Mickelson’s bag was situated behind a pile of balls and next to a tall coffee. The spot had been broken in, but Mickelson wasn’t there. A college golf team was having a long drive contest and Mickelson was right in the middle of it. He watched as one of the players reached for some extra speed and launched a deep ball. 

“That was cute,” Mickelson quipped to some laughter. “Now watch this.” He teed one up and unleashed a not-yet-patented bomb while the enamored players looked on. 

Because of Mickelson’s home-course advantage, I was offered two choices: a straight-up match in which I would get to tee off one box ahead, or play from the same tee box and get a shot a side. Because I was playing the course blind and because I lacked knowledge about it, I wasn’t sure how much of an advantage moving up a set of tees would offer. On the scorecard, the difference in yardage between the tees wasn’t substantial. I reasoned that we probably hit the ball similar distances, and by closely observing his decisions from his tee, I’d at least have an idea of what the optimal strategy was. I chose to play the same tees and take the strokes.

The first hole is a 390-yard par-4 with a somewhat blind tee shot over a hill. I had 3-wood in hand, but as my partner revisited the stakes of the bet, the head on the 3-wood looked only slightly larger than a thimble. While I had only taken a small percentage of my own action, the potential losses were significant enough to change my perception. 

As Sam’s voice echoed beyond the boundaries of the tee, Mickelson cut him off, speaking sternly but quietly. 

‍We need to practice some discretion when talking about and paying off bets today. I don’t want to invite any unnecessary scrutiny or cause a scene here. 

I changed clubs, deciding the driver looked far friendlier given the stakes. 

My hands and arms tingled as I stuck a tee in the ground. My eyes pulsed along to the rhythm of my heartbeat. I took a deep breath and stepped into the ball. I could practically hear the blood in my veins as I took the club back. I couldn’t have felt any more alive on the first tee of a major. The ball tore off the clubface down the left side of the fairway and didn’t waver. “Good shot,” multiple voices from around the tee said. The ball was safe. I was relieved.

Watching Mickelson swing for the first time while standing on the same tee was dreamlike. Here was one of the greatest golfers ever – a legend never afraid to attempt the hero shot, a player I’d watched on so many Sunday afternoons. I’ll admit it: I was star-struck. Mickelson’s ball launched high off the clubface down the right side of the fairway, the spin on the ball suspending the flight for an extra moment of added drama. 

Our partners, playing from forward tees, hit and we were off. We’d barely made it off the tee box when Mickelson asked about a trip to Portugal I had just returned from.

“I hear you just got back from Senior European Tour qualifying?”

Befuddled, I replied with something like: I know it’s Europe, but I don’t think the senior tour lets 30-year-olds play. 

Mickelson nodded and kept walking. Was it more gamesmanship? Miscommunication? Another shot fired, I guess, albeit a shank. 

To a back pin, I had about 100 yards remaining. From the other side of the fairway, about 15 yards behind me, Mickelson played a controlled shot to about 12 feet past the hole. With the adrenaline coursing, I hit a full lob wedge that covered the flag from takeoff to landing. It stuck inside two feet. 

‍Please let that be a gimmie, I begged to myself through deep breaths.

It was, and I gladly accepted. Mickelson set down his coffee and nonchalantly rolled his putt with perfect speed into the heart of the hole. 

We both hit mid-irons into a deep, short-sided bunker on 2. While he played a better bunker shot, neither of us got it up and down. 

We halved the next two holes before reaching the difficult par-3 5th. Mickelson’s birdie chance was less than 20 feet from the hole, but the ball was on the fringe with a sprinkler head directly in front of it. Mickelson probably could have negotiated a drop but instead opted for creativity, standing his pitching wedge upright so only the toe of the club touched the ground. Choking down, he made a stroke resembling something between a putt and chip, making contact on the farthest reaches of the club’s toe. The ball barely carried the sprinkler, rolled toward the hole and narrowly missed. 

The group was quiet for a moment before I spoke: “That was cool.”

As he raked the ball back to the fringe, Mickelson said, “Let me show you how to do that.” He gave a quick tutorial before we moved on. I never got the opportunity to try the shot that day, but I have used it since.

The 6th is an uphill, drivable par-4 measuring 340 yards with fescue guarding the green.

“This is my course and I play aggressively and hit the driver everywhere. But that’s not the play,” Mickelson said as I studied the hole. “For you, it’s a 5- or 6-iron out there and leaves you a wedge in.” 

As promised, Mickelson hit his driver just right of the green. It wasn’t off by much and when we didn’t see it bounce, he assumed it had caught a greenside bunker. He seemed satisfied enough. I decided it was time to fire a shot of my own, so I took the driver out of my bag. 

I was focused, calm and determined now. I made my best swing of the day. The towering draw looked perfect the whole way. I would probably have an eagle putt. Walking off the tee box, Mickelson asked if he could see my driver. I handed it over and he inspected it. 

“I know a guy who can probably get you a good deal if you’re interested,” I said, feeling clever. The atmosphere changed soon thereafter. 

We arrived at the green to find my ball about 30 feet from the hole, on the right fringe. Mickelson’s ball was nowhere to be seen. He grew more frustrated as we scoured the bunker and fescue to the right of the green. He began talking to himself, in one breath puzzled and in the next agitated, before abandoning the search and conceding the hole. First blood drawn. I was 1 up. 

Still, the comment walking off the tee had broken the ice. For the rest of the front nine, Mickelson talked candidly, like we were old friends. He gave us the inside story on the Ryder Cup, his feud with Watson, theorized why Ian Poulter was impossible to beat in singles and ranted about how his ideas for team “pods” were dismissed. He held court on the tees, talking about his speed training and how he was longer than he had been in a long time. I outdrove him for most of the day.  

In the fairways and on the greens, Mickelson described a team of scholars who used advanced metrics to predict how each player in the Ryder Cup would perform. Later, he described how he built his tournament schedule around similar predictive data and said he expected to play his worst at the Masters the following April but would have a chance to win the U.S. Open at Chambers Bay. 

He finished T-2 at the Masters and T-64 at Chambers Bay.

He was entertaining. As I continued my steady play, he hit a couple of loose tee shots. I took the lead but he barely noticed. My teams won the front nine and I took a 2-up lead through 10. He hit another wayward driver on the par-4 11th, losing his ball and the hole. I was 3 up.  

The 12th is a long par-5, and before he hit his tee shot, Mickelson remembered his objective for the day. 

“Am I 3 down?” he asked, no doubt fully aware where the match stood. I nodded. He paused and glared at me.

“I promise you won’t take a single dollar off me today,” he declared confidently. 

Over the next five holes, he barely spoke as he rattled off birdie after birdie. He would’ve had another if not for a lipped-out two-foot birdie putt that we briefly considered conceding. An unexpected gift. 

I halved one of the holes with a birdie of my own and was still 1 up when we got to the par-4 17th, my stroke hole. Mickelson carried a drive 300 yards on an aggressive line over a bunker protecting the dogleg right. There was fescue close to that line. He then tried to tempt me into a long-drive contest knowing I’d have to aim dangerously close to the fescue to win. With an acre of green grass left of the bunker and knowing I was getting a stroke, I declined and played it safe. Perhaps too safe. 

The tee shot left a long approach from the left side of the fairway to a right pin tucked behind a pond. I could take the water out of play by aiming to the safe side of the green and all but assure a 4-for-3 with the stroke. 

Whether it was my subconscious or the low hanging lie that got me, the contact was a bit thin and the ball was pushed. 

‍Please…Go! 

The ball fell a couple of yards short. Splash. 

Mickelson stayed aggressive, hitting his approach 20 feet past the hole. I took my penalty drop and hit a perfect pitch that was tracking for the cup. My partners practically jumped out of their shoes and Mickelson contorted his body to match the break of the ball, as it dove from the hole and lipped out. My partners slunk and I dropped to the ground. 

I hadn’t saved par but at the very least, I’d applied some pressure. If Mickelson didn’t hole his slippery birdie putt, I’d at worst maintain a 1-up lead heading to the final hole. But he had found the zone and when his birdie putt dropped, he had all the momentum.

We’d go to the 18th hole all square. 

The home hole is a short par-5, and Mickelson hit an almost perfect drive. I hit it slightly on the heel of the club, but right down the middle and a few yards behind his ball. 

With a slightly helping breeze, I chose a 6-iron from 207 yards. I felt suffocated by the significance of the moment. I didn’t fully trust the swing and hit a slight pull that rode the wind to the back-left corner of the green. I’d have more than 40 feet for eagle. 

Mickelson was between clubs. He debated the choice with his partner, speaking loudly enough for all to hear, narrating like Johnny Miller on the last hole of a major. 

“I was going to hit 6, but that brings the back part of the green into play where Mark is, and you can’t two-putt from there,” he said. I cringed as he continued. “But 7-iron isn’t enough. I can’t get 7 there. I’ll have to hit it perfect. I’ll just…hit it perfect.” 

Mickelson dropped the 6 on the ground and set up to the 7-iron. We had a front-row seat to watch one of golf’s best on a tear on his home course. There was a sense of helplessness watching this spectacle from the opposing side. 

The sound of the contact rang out like the final note of a Pavarotti performance and traveled like an elephant trumpeting to alarm its herd. I couldn’t have made a more distinct sound with a wooden plank on a brick wall.

“I did it,” Mickelson said before the ball reached its peak. 

The ball hung in the air seemingly forever. As it finally came down, it appeared to graze the flag. 

The closer we got to the green, the closer Mickelson’s eagle putt looked. The ball was inches from the hole.

My eagle putt was a Hail Mary. With nothing to lose, I stroked the putt freely and until the last second it had a real chance to go in. But the ball slid by. It was over. 

A satisfied Mickelson paid for lunch and held court once again. On his phone, he showed us handwritten notes he had created before the Ryder Cup, predicting how every player would perform. Bullet points led to a predictive grade for each round: A, B, C.  

‍And remember how so-and-so played? Mickelson would ask after showing us each prediction. The message was clear: He had been right. 

We adhered to the discretion demanded at the outset of the round. Bets were settled inconspicuously in the parking lot. 

I don’t remember the precise amount our teams lost, but I’m sure it was enough to buy a car any mini-tour golfer would be proud of. 

“We should do this again sometime,” Mickelson said. And with that, he was on his way. 

Billy Walters writes, “Throughout the years, I have played with many PGA Tour pros and, frankly, Phil had another gear that most others don’t have. He was also willing to put it all on the line and risk losing a golf tournament to hit one miraculous shot. A man after my own heart!”

I witnessed it first-hand: Mickelson had elevated to another level when it mattered most. 

What stands out most from that day was Mickelson’s ability to suddenly focus and find another gear when his back was against the wall. I thought I knew what it meant “to have another gear,” but I didn’t truly understand until that day. 

Not long after playing against Mickelson, I was back in Vegas, sitting on a bar stool at The Palms hotel with a professional gambler friend of mine, enthusiastically recounting the details of the match. He listened intently as I described the match and the loss. It was well worth the experience, he reassured, before reminding me of a line that could have been said by Billy Walters or Phil Mickelson.

‍It’s just money. Make more tomorrow.

‍