The Best Golf Gambling Stories from PGA Tour Stars

The Action Network spoke with several of today’s top professional golfers to find out their favorite personal golf betting stories.

The players interviewed include: Adam Scott, Justin Thomas, Gary Woodland, Kevin Kisner, Tony Finau, Paul Casey, Marc Leishman, Rickie Fowler, Rory McIlroy, Zach Johnson, Brendan Steele, Bryson DeChambeau, Corey Conners, Matt Kuchar, Louis Oosthuizen, Chez Reavie, Brooks Koepka, Justin Rose and Jason Kokrak.

Bryson DeChambeau: A Very Important Reese’s

During his early teenage years, DeChambeau became very good at the game, very quickly – and he wasn’t shy about letting his buddies know just how well he was playing. His favorite bet only resulted in a post-round candy acquisition, but it’s all about the story, one which proved to him that he could someday play high-level professional golf.

“I was about 14 or 15 years old. I was a good player, obviously, and I had a friend named Blake Berry – he’s going to hate me for telling this story – I told him I was playing really well at the time.

“We were playing from the white tees, we usually played nine holes on Saturday afternoon. I pretty much said to him, ‘Dude, I’m feeling really good.’

“He was probably a 2-handicap. And he goes, ‘Alright, what do you want?’ I said, ‘I’m telling you, four shots.’ And he says, ‘Dude, you’ve got no chance.’

“I said, ‘Really? OK, well how about this: I’ll give you a shot every hole. How about that?’ Against a 2-handicap. And he goes, ‘What?! You’re crazy.’ I said, ‘Just watch.’

“So I birdie the first three holes. He pars each of them and we’re even. I eagle No. 4 and par 5, then birdie 6, birdie 7, birdie 8 and birdie 9 to shoot a 27. I had a 4-iron into the last hole and hit it to a foot. I played the best I possibly could.

He shoots 37, bogeys the last hole and I beat him by one. He had to give me a Reese’s afterward. That was the bet.

“That’s when I knew I could do it. That’s when I knew I could play out here, that I had the you-know-what that it takes to play out here.”

Corey Conners: Pressing at Pebble Beach

During a practice round for this year’s AT&T Pebble Beach National Pro-Am, Conners teamed with fellow Canadian pro Mackenzie Hughes in a four-man match that was never going their way. They kept pressing the bet, meaning it all came down to the famous par-5 final hole at Pebble.

“I was playing with Mac Hughes against Nick Taylor and Brandon Harkins, I think. Well, Hughes and I are getting killed all day.

“We were pretty worried for a while. We were getting in a little over our heads.

“We kept doubling the bet.

“I remember when I was a kid, we used to play a little chipping contest for a cookie at the snack shop – a Coke or a cookie, something like that.

“I think when you put yourself in those situations, you still feel the pressure – whether it’s for 20 bucks or playing out here for big money. It definitely keeps you focused and gets your nerves up a little bit, but it’s great practice. I think it’s really helped me become comfortable under pressure situations.

“Back home in Florida, the guys I play with are always bantering back and forth, getting in each other’s heads. It makes things tough, it stresses you out a little bit on the course, but it’s good practice.

“[After pressing at Pebble], I made a 4 on 18 to square it up, so we owed nothing at the end. I had like a 15-foot putt. It was playing too long, so I layed up and hit a wedge to 15 feet and made it.”

Matt Kuchar: A Costly First Albatross

To say Kuchar was a successful amateur golfer is an understatement. He won the 1997 U.S. Amateur and the next year earned low-am honors with a T-21 finish at the Masters and a T-14 at the U.S. Open. But he didn’t win everything during those years. In fact, it was a lost bet with a Georgia Tech teammate that still resonates to this day.

“I distinctly remember losing to my best buddy Carlton Forrester in college. I didn’t have much money to my name, but we were playing for some decent money.

“I was playing great golf, but I was down to Carlton. I doubled the bet on 17, but he birdied to beat me.

“Then I doubled the bet on 18 and he made an albatross.

“That really hurt. That was my first time ever witnessing an albatross and not the one I wanted to see.

“It took me a couple of installments to pay him back. It might have only been 100 bucks total, but that was a couple of installments for me at that time.

Louis Oosthuizen: A South African Showdown

It’s not often that two childhood buddies each become major champions, but that’s the case for Oosthuizen, who won the 2010 Open Championship, and Charl Schwartzel, who won the 2011 Masters. About two months after Schwartzel’s win at Augusta National, the two friends were playing a practice round match in advance of the U.S. Open. Unlike most friendly matches, their recurring game features a cruel twist – one which came back to bite Oosthuizen on this occasion.

“We’ve got this recall-mulligan game that we play. If your opponent hits a good shot, you can make him recall it and take a mulligan.

“On the long par-4 15th, it’s a dogleg down to the left and Charl hit one into the fairway bunker. He had 210 yards into the pin. The only way he could do something is if he hit this 40-yard cut 5-wood, because he couldn’t go straight over the left.

“So, he hit this shot to 25 feet, an unbelievable shot. I immediately go, ‘Recall!’ I hadn’t used my recall yet.

“He was swearing and shouting. He said, ‘You can’t do that!’ I said, ‘Hey, that’s the game.’

“Well, he hit the next one to 10 feet.

“He placed it exactly where he wanted to and it stopped 10 feet away. That screwed me completely. He ended up making birdie and he beat me that day.

“We’ve always had good matches between us.”

Chez Reavie: Taking on Lefty at East Lake

Before this year, the last time Reavie qualified for the Tour Championship was eight years ago. He finished in a share of 26th place that week, but the most memorable moment might have taken place before the event ever started, as he competed in a practice round match alongside some big-name fellow pros.

“You know, we have a lot of ‘em at Whisper Rock, a lot of fun matches with good players who give each other a bunch of shit when they’re playing together.

“But I had a good one [at East Lake] the last time I played the Tour Championship. It was Dustin [Johnson] and I against Keegan [Bradley] and Phil [Mickelson]. It came down to the last hole.

“It was when the par-3 [now the ninth hole] was the last hole. Dustin knocked it on the green, I missed the green, but I chipped it up there close.

“We ended up tying with pars and pushing the match. It was exciting. We had guys come out and follow us the last couple of holes, just because they heard what was going on.

“I think we were all happy we tied. I was playing for a little more money than I normally do, so it was a nice to not lose anything.”

Brooks Koepka: I’m Still Waiting To Get Paid

When asked his favorite on-course betting story, the world’s current No. 1-ranked player first starts to tell a tale of losing to a certain fellow pro during an Open Championship practice round without having any cash on hand. He then remembers a practice round for the U.S. Open four years ago, when he didn’t even need his clubs to bank a wager.

“I once played against Phil [Mickelson] with no money in my pocket. That was at Muirfield in 2013 – and we lost.

“Had a good one at Chambers Bay, too. I was probably 80 yards away and I looked at my caddie and we made a bet.

“Well, I threw it into the cup. Straight in, which I thought was pretty impressive.

“Yeah, first try. Just went right in.

“I still haven’t seen the money. Still haven’t gotten paid. I’ll be alright, though.”

Justin Rose: The Worst Social Golfer There Is

While most professional golfers enjoy a little side action during non-tournament rounds, Rose doesn’t usually play for anything when he’s preparing for an event. In fact, the man who’s probably won the most bets against him isn’t a fellow elite-level player, but a largely unknown former pro who once spent a little time playing the Sunshine Tour – his half-brother, Brandon Harcus.

“Generally, I’m the worst gambler. I’m the easiest guy to take 10 bucks off of, I’m the worst social golfer there is.

“For me, I don’t know what the number is to make it feel like it should matter, but I don’t necessarily like playing for that number, because I don’t play a lot of golf when I’m not on Tour. I probably play four rounds of golf per year that aren’t professional rounds of golf. It’s just not something I do. I practice, I hit balls, I get away from the game and spend time with my family.

“On the gambling side of things, I’ve never really done much of it out here.

“My brother loves it. My brother thinks he’s the best putter on the planet. If he manages to hole one, he’s got all the bravado and the swagger before he hits a putt.

“He’ll be standing over a 6-footer to take your money and say, ‘You know what? The last time I missed one of these, they cut one of my fingers off.’ Then he’ll show his 10 digits and roll in the putt to take my money.

“Not only does he take my money, he literally rubs it in my face, too. He actually does have a great short game. If he could drive the ball, he’d be dangerous.”

Jason Kokrak: He’s Still Pretty Salty

Prior to last year’s Players Championship, Kokrak was invited to play in a nine-hole practice round match. After securing a partner and getting off to a rough start, he vividly remembers how the bet finished – and we’re guessing his opponents still remember, too.

“I gamble a little bit, but it’s mostly with certain people. I won’t name any names, but the most fun I’ve had was at TPC Sawgrass a couple of years ago.

“We had a few bucks on it – not enough to make you sweat, but enough that it was going to keep your head in the game.

“I actually had a hard time trying to find a partner to play against the two guys who wanted a match. I finally found a partner that morning. It was just a straight-up, nine-hole bet for a set amount of money.

“We teed off on No. 10, both sprayed it, and we were 1-down. Then we traded birdies for a couple of holes. We were 1-down going to 16. I hit a 5-iron to about 12 feet. This ‘gentleman’ – one of our opponents – was standing pretty close to me, breathing down my neck. I poured it right in the middle.

“Then we all par 17. On 18, two of us hit it just over the back fringe to a middle pin, so if you putt it just two feet by, it’s going 20 feet down the hill. The other two missed it short. They chipped up and made their pars.

“I was up next and I putted it and I mean, the greens were running 15 on the Stimpmeter. It took about five minutes for this ball to get down there, but I dropped it right in the cup.

“Our opponent was staring at me so bad. We actually haven’t had a match since. He’s still pretty salty about it.”

Adam Scott: Fred Couples, Phil Ivey and $10K

Scott rarely plays money games, but was part of a memorable one nearly a decade ago, playing with Fred Couples and professional poker player Phil Ivey. They started with a small bet, which quickly ballooned into a much bigger one — and then another.

“We had a really soft bet at the start of the round and [Ivey] wasn’t happy about it. Fred and I were playing pretty lackluster golf the first five holes and he said, ‘I didn’t come out here to watch you play like this, but I’ll bet that you can’t make 10 birdies between you for the rest of the round, from the sixth hole on.

“It was a $5,000 bet. I was pretty sure that Fred and I could handle it, so we agreed to the bet.

“We had it all under control, then we slowed down. I should’ve birdied 16, but I didn’t, so we needed three birdies between us for the last two holes.

“The 17th is just a wedge par 3 to an island green and the 18th is a reachable par 5.

“On the 17th tee, Phil knew his chances weren’t very good. It was likely one of us was going to stiff a wedge and both of us could birdie the last. So, he threw a curveball at us. He said, ‘I’ll bet you another five grand that you both can’t hit this green.’

“I’m like, oh my goodness, this is too good to be true. He’s giving us five grand to hit the green on a 140-yard hole.

“We take the bet. Freddie gets up there first. I think he was thinking so much about the second bet that he fanned it into the right bunker. It was just devastating, because now we’ve lost that bet and we might lose the first one.

“I hit it on, but only made par. So it was a lost cause. We both birdied 18, but came up one short, so we were scrounging around for the checkbooks.

“It’s a really good story, but I was completely devastated.”

Justin Thomas: 36 Holes with Michael Jordan

Each year, Michael Jordan and a group of friends would travel to the Kentucky Derby, arriving a day early to play 36 holes at Harmony Landing, where Mike Thomas was (and still is) the head professional and his son Justin was a ubiquitous presence around the course.

Justin spent a few years caddying for Jordan before finally getting the call to play, teaming up with MJ for a memorable match.

“We don’t have caddies or tee times at our course, but they wanted a caddie, so I would go out with them. The first year, I was probably 13. I’d just get out of school; I was going to learn a lot more out there than I was in school.

“The first few years, I’d just caddie. When I was 16, I went out with the group and they started on No. 3 for some reason.

“I was riding with MJ. When we got to the first hole, he said, ‘Go get your clubs.’ He told them, ‘Alright, I’ve got the little man. We’ll take whoever wants us.’

“There’s eight people. He wouldn’t tell me the game; he said I didn’t need to hear that.

“Everyone’s giving me grief, because I was playing the same tees as them. I was tiny when I was 16.

“So we played the last seven holes and I made four birdies. We drummed ’em pretty good. That was fun.

“He just made me feel comfortable. I’d played in some big national tournaments, but that was the biggest deal I’ve ever played in. It was pretty cool. We had a pretty memorable day that we still talk about.

“He always took care of everybody tipping, so let’s just say my tip was a little bigger that year.”