Here are 10 outrageous Phil Mickelson golf gambling stories

phil mickelson gambling

Before there were sponsors or cameras or golf carts or famous quarterbacks or names like The Match: Champions for Charity, there was still Phil Mickelson, legendary gambler. In many ways, what the televised match with Tiger Woods, Tom Brady and Peyton Manning is attempting to replicate is the sort of four-man money game Mickelson has played thousands of times over the years. Here are 10 of our favorite stories involving Mickelson, money, and mischief.

He needed a loan to pay off this bet at Augusta

In 2014, Mickelson was playing a Tuesday practice round with Jason Dufner, Dustin Johnson and Rickie Fowler when one patron got in his ear. Mickelson was just off the green at the par-3 6th when he started to hear from a member of the gallery.

“He was mouthing off — ‘hard shot, get this up-and-down, no chance’— blah, blah, blah,” Phil recounted in a press conference afterwards. Mickelson accepted a wager from the fan: he’d get it up and down, for a dollar. “And it wasn’t that hard a shot and I should have gotten it up and down. And I did hit a good shot. I had a 7-footer straight up hill.”

But Mickelson missed. Dismayed, he had to borrow a small bill from Jason Dufner’s caddie because he doesn’t carry any of his own. And then he paid up in this wonderful picture.

Tin Cup trickery

Cheech Marin recounted a fantastic story of Mickelson’s legendary flop shot prowess as a part of’s Tin Cup oral history. “I’ll tell you a story no one’s ever heard,” he begins. That’s always a good place to start.

“We were between scenes, standing around, and someone came up with a bet. There was this really tall pine tree, and someone said to Phil Mickelson, “I bet you can’t put your shoulder against the tree, drop a ball and hit it over the tree.” The shot basically had to go straight up. Everybody threw in a hundred bucks. I think there was $1,200 in the pot. And he did it! When the ball was still in the air, Mickelson bent over, picked up the money, and put it in his pocket.”

It’s hard to imagine a more fitting film set for a golfer to hustle his audience than that of Tin Cup; it’s easy to imagine using the scene in the movie itself. Maybe they’ll save it for Mickelson’s biopic.

Down goes Keegan

Mickelson joined Alan Shipnuck on a podcast for a wide-ranging discussion that included a gem of a story about a Tuesday money match where Mickelson and Rickie Fowler took on Keegan Bradley and Brendan Steele. Take it away, Phil:

“Now, Keegan is about ready to bow out of these games because he’s never won. It’s been a year and a half and he’s paid every time. And it gets demoralizing. So he’s like, ‘If I don’t win today, I’m out. … This is the day. This is the day I’m going to win.’

“Fast forward to the 12th green. Keegan and I have about a 16-footer and 14-footer, and I’m away. Now they’re 2 up. They’re 2 up. And as I’m standing over this putt, I back away, and I say, ‘Oh my goodness, this putt is the entire match.’

“And Keegan bit, and he goes, ‘Oh yeah, how so?’ which is what I was hoping he would say.

“And I said, ‘Well, if I miss, you’re going to make your putt. You have momentum, you’re going to make it, and you’re going to be 3 up with six to go, and you guys are going to win. But if I make it, you’re going to quick-peel yours low side. You’re going to be so pissed off, you and Brendan are going to give us a hole. Next thing you know, we’re going to be tied, Rickie and I are going to have momentum, we’re going to make a birdie or two coming in, probably beat you, 2 and 1.

“So I knock it in. I knock it in. And of either side he could have missed it on, he missed it low side. He quick-peeled it low side. Now they’re so pissed off, they both bogey the next hole, and we get that hole and now we’re tied. So Rickie and I birdie 15, 16 and 17, and win, 2 and 1.

“And I just chuckle about the story every time I hear it, because it’s just funny. And I don’t care about the money. I just love being able to – and I give him smack about this every time I see him.”

Phil on the phone

This one comes courtesy of Tour pro-turned-Subpar host Colt Knost, who revealed the story on the Action Network’s podcast. Knost told Mark Gallant about a round that he played with Mickelson, Ben Crane and an anonymous TV writer who was getting plenty of strokes. Here’s how Gallant laid it out:

“Lefty insisted on playing with Crane, leaving Knost and the high-handicap writer to pair up in a money match, with the latter getting 24 strokes. As Knost puts it, this writer was only driving the ball 200 yards, so they wanted him to be able to play a tee up. Can’t have an amateur playing from the 7,400-yard back tees at the Madison Club against tour pros.

Phil was reluctant at first, but eventually agreed. They teed off the first hole, with the writer getting about a 30-yard advantage. The second hole comes around, and the gap between the tee boxes is not quite as far.

By the fourth or fifth hole, the tee boxes were just a few yards apart, and Phil shot Colt a look.

It was at that point, Colt realized what was going on.

“This son of a bitch …”

Phil had called the pro shop and had them move all of the next-to-back tees closer to the tips, taking away the slight advantage Knost and his teammate thought they were getting.”

“That was a veteran play by Phil and a very impressive one,” Knost said in conclusion.

The moment Azinger knew

Our next chapter comes courtesy of Paul Azinger, who told a marvelous story on PGA Tour Radio about Mickelson’s penchant for final-hole theatrics. Here’s Zinger’s story, transcribed (but you can hear the audio here):

“I had some big games with Mickelson. He was virtually unbeatable. Payne Stewart and I were playing Ben Crenshaw and Mickelson. By the time we got to the 18th hole at Bay Hill, it had gotten a little out of hand … We get to the last hole, and it’s like $1,600. We get to the 18th green, and we all have birdie putts. Mickelson is the closest, and he has about a 14-15 footer down the hill. We all miss … If (Mickelson) makes it, we lose $1,600. If we beg out, we forfeit $800. But if he misses it, we only lose $400. So Payne says, ‘I’m out.’ I said it was downhill, right-to-left. He’s not making it.

So Crenshaw jumps in and says, ‘I’ll take Payne’s side.’ So he gets his guaranteed $800. I looked at Mickelson, and I don’t know if I can say this, but I said, ‘Putt it, bitch.’ Mickelson looks at me and walks over to the putt. Dead center. He makes it dead center and smiles. Payne starts smiling and high-fiving Mickelson because I just lost $1,600 and he only lost $400. I was so mad. That’s when I knew Mickelson was going to be a really good player. I just knew it.”

Mind the conversion rate

Shane Ryan recounts for ESPN a story from across the pond involving Mickelson and Nick Watney. The two played a practice round at St. Andrews alongside Dustin Johnson in 2010 with a simple format: Worst score pays the best score 1,000 bucks. Watney objected, but after some name-calling, he said “I gave in to peer pressure.”

Sure enough, Watney lost and Mickelson won. But when Watney handed over $1,000 to Mickelson, Lefty handed it right back. “This is Britain,” he told Watney. “I need pounds.”

Watney had to chase down the rest of the debt, which totaled about $1,700. “They’ve asked me to play again,” Watney told ESPN. “And now I just say ‘f— you’ and walk away.”

Fight Night!

Mickelson’s affinity for pay-per-view may come from his enjoyment of another mano a mano showdown sport: boxing. Jason Sobel detailed a series of gambling stories for the Action Network, including one on a night he’d spent at a party Mickelson was hosting.

Sobel writes that the main event of the night was a Floyd Mayweather fight against Robert “The Ghost” Guerrero, but it was an undercard match that caught Mickelson’s attention. Here’s how he sets up the story:

“He explained that the next bout featured Alexander Munoz, a man with the brilliant nickname “El Explosivo,” who counted 28 knockouts among his 36 career victories. He told the room that Munoz would be fighting against Leo Santa Cruz, who was not only 10 years less experienced, but he was moving up a weight class that night to challenge for the super bantamweight title.

Then, like an experienced fisherman chumming the waters for his prize catch, Mickelson offered a wager.

‘You know,’ he said, as if the idea had just suddenly percolated in his mind, ‘I’m sort of liking this young kid. If anyone wants the favorite, I’ll take that bet at even money.'”

You can only guess what happened next. Santa Cruz was dominant from the start, and the referee granted him a TKO in the fifth round. Mickelson made his way around the room, collecting cash. Sobel lost $100. “Most of the bets were bigger than mine. A few were much bigger.”

Read his full account here.

Why Anthony Kim refused to gamble with Michael Jordan
By: Dylan Dethier

“He’s young…”

Mickelson doesn’t just take on seasoned Tour vets; playing money matches against Lefty can be a rite of passage for some young stars. One such player? Ryan Ruffels, a 17-year-old Australian phenom at the time, joined Mickelson and his brother, Tim, for a round (he was considering attending Arizona State at the time). Ruffels recalled the sequence of events for the Sydney Morning Herald.

“We get on the first tee, it’s pretty early in the morning and he says, ‘I don’t wake up this early to play for any less than $2,500’,” Ruffels recalled of a friendly offer made to him by Mickelson. The 42-time US PGA Tour winner gave Ruffels 2-1 odds; if Ruffels won, Mickelson would give him $5,000, if he lost, Ruffels would have to pay up $2,500 when he turned professional.

“I was a few down through nine but then I birdied six of my last seven to win by one shot and took his money, so that was pretty cool,” Ruffels said with a laugh.

But Mickelson didn’t take too kindly to Ruffels’ violation of their code of trust. After the story began to make the rounds, Ruffels’s team tried to walk back the details, citing “overdone” reporting about “friendly wagers.” Mickelson didn’t mince words at a Farmers Insurance press conference.

“He’s young,” Mickelson said, “and he’s got some things to learn.

“One of them is you don’t discuss certain things. You don’t discuss specifics of what you play for. And you certainly don’t embellish and create a false amount just for your own benefit. So those things right there are – that’s high school stuff, and he’s going to have to stop doing that now that he’s out on the PGA Tour.”

The original Tiger vs. Phil

Doug Ferguson of the AP reported that the first time Woods and Mickelson squared off for money, it was Lefty who emerged victorious. The two young Southern California superstars squared off in the leadup to the 1998 Nissan Open. According to Ferguson, Mickelson won big. Afterwards, he put photocopies of Tiger’s $100 bills in his locker. He also included this note, as passed along via Shane Ryan for ESPN:

“Just wanted you to know Benji and his friends are very happy in their new home.”

Keep the change

We’d be remiss to make it through this entire list without acknowledging that in The Match Vol. 1, Mickelson came out on top over Woods to the tune of $9 million. One exchange from the after-party still stands out as Phil in Full, though.

Country singer (and massive golfer) Jake Owen wasn’t particularly impressed with the level of competition put on display, and after a few drinks he was ready to let Mickelson know.

“So I walked over to him. I was like, ‘Hey Phil, you owe me f—— $29.99!” Owen said on Barstool Sports’ Fore Play podcast, referring to the pay-per-view price. “I was like, ‘For wasting four hours of my life with the s——- golf I’ve ever seen! You guys hype this whole thing up about the big match? You guys couldn’t even make three birdies between the two of you? I want my $29.99 and apologize to me for some s—– golf.’”

Mickelson wasted little time.

“He pulls out a wad of his thing and he grabs $100, like, a $100 bill,” Owen said. “And he’s like, ‘Yeah — I won 90,000 of these yesterday.’ He goes, ‘Take a 100 and go f— yourself!’”

To top it off, Mickelson confirmed the account himself.

Good news for golf fans: Mickelson appears to have every intention of continuing to add to this list.

Dylan Dethier

Dylan Dethier Editor

Dylan Dethier is a senior writer for GOLF Magazine/ The Williamstown, Mass. native joined GOLF in 2017 after two years scuffling on the mini-tours. Dethier is a graduate of Williams College, where he majored in English, and he’s the author of 18 in America, which details the year he spent as an 18-year-old living from his car and playing a round of golf in every state.