The legendary gambler named Phil Mickelson existed prior to the arrival of famous quarterbacks, golf carts, cameras, sponsors, and names like The Match: Champions for Charity. 

We can authoritatively say that the current famous names like Peyton Manning, Tom Brady, and Tiger Woods are all trying to achieve the type of fame the four man money game that was played by Mickelson and others about a thousand times a very long time ago with their current televised matches. 

Some of the tales that made this list are not to be taken seriously and if you’re looking for gambling stories or a site offering casino games or slots, check out some of the sites found at Casimple where you find some of the top new online slots available to players. Now, we have succeeded in organising some of the favourite stories surrounding Mickelson, and his sojourn with mischief and money.

At Augusta, he needed a loan to settle a bet

Mickelson was involved in a game of golf with Rickie Fowler, Dustin Johnson and Jason Dufner on a Tuesday in 2014, when he overheard one patron while off the green at the par-3 6th. The man at the gallery at the moment was saying, ‘that’s a hard shot’, ‘no chance of getting up and down’, and some other things according to Mickelson.

That made him get into a wager with the fan, which involved him getting it up and down for just a dollar. He later said that he could have achieved that because it was never a hard shot. He got a good shot involving a 7-footer straight up hill.

The conclusion of the entire episode is that Mickelson missed the shot, and in his dismay, Dufner had to lend him some cash because he doesn’t go out with any. He later paid up in a very amazing manner, with pictures to show for it.

Tin Cup trickery

It was Cheech Marin that narrated Mickelson’s amazing power of the flop shot as one of the stories in the Tin Cup oral history on He started by exclaiming that he is about to tell the world a story that has never been heard by anyone, and we all know that such start is always amazing to use.

Marin went ahead to say that they were lounging between scenes before someone suggested a bet. A very tall pine tree was standing in front of them, and someone bets Mickelson that he can’t lay his shoulder on the tree, drop a ball, and hit it over the tree. And, the shot in question will only need to go up. This made all the people around to bring a hundred bucks bet each.

At the end, the pot had $1,200 in wager money. Mickelson did the challenge, and while having the ball up in the air, he stooped low, picked the wager money and slotted it into his pocket. The scene seemed very fitting for a film.

As it involved a golfer hustling his audience, it easily would have made an excellent scene in a movie. This will probably be preserved for his biopic.

Keegan goes down

Alan Shipnuck was joined on a podcast by Phil Mickelson, and they had a very lengthy discussion that included many topics like the ‘Tuesday Money’ match that saw Rickie Fowler and Mickelson square up against Brendan Steele and Keegan Bradley.

The story has it that because Bradley never tasted victory in any of these games, he was about giving up. For a year and half, he has been paying all the time, and has never gotten paid, and this can demoralise anybody.

“Because of this,” Mickelson explained, “Keegan went, ‘If I fail to win today, I’ll never do this again. Today is the day that I’ll win.’”

Now, the game got underway and when they got to the 12th green, Mickelson and Bradley had a 14-footer and 16-footer respectively, and Mickelson was aware. They are 2-up at that moment, and as Mickelson stood over the putt he stepped back and shouted: “Oh my goodness, this putt is the whole match.” This got to Bradley, and he asked: “Oh yeah, how is that possible?” Mickelson actually expected to hear this from him.

Mickelson responded: “Well, if I miss, you will have your putt. You will achieve it because you’ve got the right momentum, and you’ll be up by 3, with 6 remaining, and the victory will be yours. But if I succeed, you’ll be in for a bad day. You will be so vexed and you and Brendan will hand a hole to us. Before you say jack, we’ll be tied. The momentum will become mine and Rickie’s, we’ll achieve a birdie or two getting in, and probably defeat you by 2 and 1.”

Every time this story is told, it makes me chuckle, because of how funny it is. And, the money has never been of huge importance to me, I just love to defeat him, and rub it in his face whenever I see him.

Phil on the phone

This is coming from a former tour professional that is now a Subpar host, Colt Knost. He told Mark Gallant the story on a podcast by Action Network. Knost was narrating a golf round he had with Ben Crane, Phil Mickelson and one other unnamed TV writer that got a lot of ass whooping.

Knost started the story by saying that Lefty chose to go against Crane, and this left the high handicap writer to pair with Knost in a money match, where the writer got 24 strokes. According to Knost, the writer could only drive the ball 200 yards, so they are trying to get him to be ready for a tee cup, because it is irritating to watch an amateur play from the Madison Club’s 7,400 yard back tees against tour professionals.

Phil never liked the idea in the first place, but he later gave in, and the first hole was teed off, giving the writer an advantage of up to 30 yards. It was time for the second hole a few minutes after, and there wasn’t much gap between the tee boxes.

By the time they got to the fourth or fifth hole, the space between the tees boxes was just a few yards, and Phil gave Knost a very stern look. That was when Knost understood what was in play, and exclaimed: “This son of a bitch…”

This led to Mickelson calling the pro shop and getting them to move all the next-to-back tees some yards closer to the tips, and this made the little advantage that Knost and his team-mate believed they had disappear. That play by Phil is the stuff of veterans, and the move was very impressive, said Knost.

The moment Azinger got informed

Paul Azinger is the man in the next story. He talked about the ‘final hole’ theatrics that Phil Mickelson enjoyed so much on the PGA Tour Radio.

Azinger’s story revealed that he got involved in some big games with Mickelson, who was practically never to be defeated. He played with Payne Stewart against Mickelson and Ben Crenshaw.

“It took place at Bay Hill, and when they got to the 18th hole the game was already out of control,” Azinger explains. “By the time it was the last hole, there was up to $1,600.

“At the 18th green, they all had birdie putts. The closest is Phil and he was down the hill with a 15 footer. So, if Phil succeeds, we will all be down by $1,600. But we can let go of $800 if we beg it out. However, if he fails, we will only lose $400. But Payne said he’s out, he had said it was going downhill, from right to left, and he can’t make it.”

So, in comes Crenshaw, who posited that he’ll replace Payne. So, he has $800, guaranteed. Azinger gave Mickelson a stare, and was not sure of the consequence of what he wanted to say, but he went ahead and said, ‘Putt it, bitch.’ Mickelson gave him a stare too, and walked to the putt. He made it dead centre and gave out a smile.

At that point, Payne gave out a huge smile and a high five to Mickelson because Azinger just became $1,600 poorer, while he lost only $400. That made Azinger insane, and there and then, he realised that Mickelson would become a great player in the future. His intuition just told him that.

Subscribe to NCG


PGA Catalunya Stadium PGA Catalunya Stadium

The NCG Top 100s Tour is heading to Europe for a multi-day event at PGA Catalunya. Prices start at £799 per golfer.


Subscribe to NCG