Sobel: Imagining How Tiger and Phil’s Big-Money Match Would Play Out

Sobel: Imagining How Tiger and Phil’s Big-Money Match Would Play Out article feature image

Credit: Rob Schumacher-USA TODAY Sports

The Highlights

  • Phil Mickelson wants to play a “winner-take-all match” against Tiger Woods. Woods said, “We’ll play for whatever makes him uncomfortable.”
  • “I’ll press,” would be a common refrain from Phil during the match.

PONTE VEDRA BEACH, Fla. — So, you might have heard by now: Phil Mickelson enjoys a little action.

Just in case you hadn’t, Lefty doubled down on Tuesday. (Not his first time doubling down.) Asked about playing in the same group with Tiger Woods for the first two rounds of this week’s Players Championship, Mickelson went all-in with his comments. (Not his first time all-in, either.)

“The excitement that’s been going on around here, it gets me thinking,” he said during his pre-tournament news conference. “Why don’t we just bypass all the ancillary stuff of a tournament and just go head-to-head and just have kind of a high-stake, winner-take-all match. Now, I don’t know if he wants a piece of me, but I just think it would be something that would be really fun for us to do, and I think there would be a lot of interest in it.”

Not long after, Tiger had this to say in his press conference: “I’m definitely not against that. We’ll play for whatever makes him uncomfortable.” (Mickelson often says this of money matches: “We play for enough to keep you interested, but not enough to make you uncomfortable.”)

Immediately, reactions on social media were fully in favor of this idea.

Bring back the old primetime head-to-head events!

Let ’em play for a million bucks!

Let ’em play for a million bucks … of their own money!

Hopefully, Mickelson’s comments actually prompt this to happen — and sooner rather than later.

When it does, here’s how it might play out.

The Prologue

After the two players warm up on opposite sides of the practice range, Mickelson arrives to the tee first, a full seven minutes before tee time.

He fist-bumps all 1,458 fans in the capacity attendance around the tee, kisses seven babies, hands out four autographed gloves and takes a selfie with three former presidents.

Woods arrives five minutes later. Without breaking stride, he methodically tips his cap to the crowd and starts checking the pin sheet.

At this point, Mickelson walks up to his opponent for some pre-planned mind games.

“You know,” he tells Woods, “I’ve spent the last two months adjusting my sleeping pattern, so my body clock is perfectly in tune for our tee time.”

Woods never even looks up.


“Also,” Mickelson continues, “I’ve noticed that the denser air at this time of day has resulted in my shots flying exactly 1.3% shorter, which is why I’m carrying two drivers, four 3-woods, a 1-iron and six wedges. It’s the only play, really.”

Woods continues to ignore him.

“And,” adds Mickelson, “I had my usual pre-round meal of tacos. They’re not only full of nutritional value, they remind me of my victory in Mexico, which was huge because I hadn’t won in almost five whole years. Can you imagine that? Not winning in five years? Man, I’m glad I don’t have that weighing on me.”

Finally, Woods speaks.

“I’m playing a Bridgestone 1,” he says, then returns to studying the pin sheet.

The Match

Woods is no stranger to wayward opening drives, but this one is especially nervy.

With all of Planet Earth to the left, he pushes the drive so far right that even the marshals never see it. Woods slams down his driver and watches as Mickelson launches a beautiful, high-arcing fade down the left side of the fairway.

Before it ever touches land, Woods mumbles, “That’s good,” conceding the hole as a bemused Mickelson plays to the crowd with a shrug and a smile.

The two split the next two holes with pars, as it feels like the fireworks forecasted for this match might never unfold.

That feeling doesn’t last long, as Woods wins the fourth hole with a birdie.

What happens next can only be described as Mickelsonian.

Mickelson cards a double-bogey on the fifth hole, moving back to 1-down against Woods, who made par. He then eagles the sixth to square the match again. Then another double, another eagle and another double — a classic Mickelson scorecard with all the volatility of cryptocurrency stock.

As they make the turn, Woods leading 1-up, Mickelson sidles up next to him on the 10th tee and declares, “I’ll press.”

Woods looks at him incredulously, then smiles.

“What are you pressing?” he asks.

“The overall,” Mickelson replies matter-of-factly, his tone implying he’s surprised at the query.


Woods accepts the press, then blasts a drive down the fairway and fires a 7-iron to gimme range for birdie and a 2-up lead.

As they walk off the 10th green, Mickelson again gets within earshot.

“I’ll press,” he tells Woods.

“You’re pressing the press already?” Woods asks.

“Well,” Mickelson says, “I mean, if you don’t have the cash on you, just pay me tomorrow. I don’t mind.”

With that, Woods laughs, sets up for his tee shot on the par-3 11th, and hits another dart right at the stick. He wins this hole, too, and as they walk toward the 12th tee, again Mickelson has an idea.

“I’ll press,” he tells Woods.

By now, the two of them are just laughing, their muddled scorecards already resembling something out of “A Beautiful Mind.”

When Mickelson wins the next hole, Woods can barely stop laughing long enough to proclaim, “I’ll press that last press.”

To which Mickelson smiles and offers his familiar thumbs-up.

The match continues this way for the remainder of the back-nine, each player throwing haymakers as the bets continue to pile up, one on top of another.

The Epilogue

Upon completion of the match, the two men — formerly bitter rivals, once Ryder Cup partners with a disastrous result — remove their hats, shake hands and talk about how much fun they just had, and how they need to start making this a regular thing.

Soon enough, it becomes one.

Just not Tiger against Phil anymore.

Instead, they team up in a series of partnered, two-man, prime-time matches against other big-time players.

Tiger and Phil against Jordan Spieth and Justin Thomas. Tiger and Phil against Rory McIlroy and Rickie Fowler. Tiger and Phil against Dustin Johnson and Jon Rahm.

Each of these matches includes lots of laughs, a ton of bets and, eventually, a Tiger and Phil victory together.

As for which one of them won that first match, well, I could tell you. But what fun is that? As Mickelson knows, there’s nothing like a little action. So place your bets on that winner-take-all, high-stakes match. Who you got: Tiger or Phil?

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