It all starts with 5 $100 bills

In February 1998, Tiger Woods played a practice round with Phil Mickelson ahead of the Nissan Open at the Valencia Country Club in California when both men were in their 20s. The pair had agreed to a bet, with the winner taking $500 from the other.

By the end of the round, Mickelson emerged victorious. He celebrated by putting photocopies of his five winning $100 bills into Woods’ locker with a note that read: “Just wanted you to know Benji and his friends are very happy in their new home.”

“Woods seethed,” writes author Bob Harig in his new book “Tiger and Phil – Golf’s Most Fascinating Rivalry” (St. Martin’s Press), out this month, noting that the pros wouldn’t play another practice round together until 20 years later at the 2018 Masters.

The complex relationship between the two greatest players of their generation has fascinated the golf world for decades, with their lives and careers inextricably linked. Yet the two men couldn’t be more different.

A friendly wager over $500 during a practice round before the Nissan Open in 1998 (above) left Mickelson happy while Woods seethed.Getty Images (2)
Mickelson, 51, is a white country-club kid with an airline pilot for a dad; Woods, 46, is mixed race with parents who took out a second mortgage just to help their son make it in the sport. Mickelson is famous for signing autographs till his pen runs out of ink; Woods is known for being standoffish and aloof. Mickelson is a family man with three children who took time off to care for his wife, Amy, when she was diagnosed with cancer in 2009. Woods was exposed as a philanderer when his wife, Elin, chased him out of their house with his own golf club and used it to smash the windows of his car.

“Theirs isn’t a rivalry in the classic sense,” Harig writes. “But Woods has always been aware of Mickelson, and Mickelson has certainly always been aware of Woods.”

The two men do have a few similarities. They were born in California, and both were destined for greatness.

“I felt like history needed it,” said one pro of pairing Woods and Mickelson at the 2004 Ryder Cup.Getty Images

Woods, the son of a Vietnam veteran and a Thai mother, was groomed for golf as soon as he could walk. When he left Stanford University after just two years to turn pro in 1996, he had a $40 million contract from Nike and Titleist waiting for him.

Mickelson was a right-hander who played the game left-handed, a super-confident, superstar collegiate golfer at Arizona State University who honed his skills on his own personal practice facility in his backyard.

And yet, despite 45 Tour wins, including six majors, and raking in nearly $100 million in prize money alone, Mickelson has never made it to No. 1 in golf’s world rankings, despite being in the top 10 for 700 weeks and spending five years in the number two spot — always behind Woods.

Mickelson wins the Tour Championship and Woods wins the FedEx Cup in the final round of the 2009 PGA Tour Playoffs.US PGA TOUR
In any other time, Mickelson’s career would be the stuff of legend. In this time, he’s nearly always been known as second best. “I oftentimes wonder what my career would be had he not come along,” Mickelson said in November 2018.

The 2001 Masters, when Woods completed the “Tiger Slam” of holding all four major titles simultaneously, is a case in point. Paired together in the final round, Mickelson played the best golf of his life in the first nine holes but Woods kept him at bay, eventually grinding him down and taking the Green Jacket.

“It was really frickin’ hard to play Tiger back then,” Mickelson later admitted.

Phil Mickelson struggles at the 2006 US Open, blowing the win on the final hole while Tiger Woods, who missed the cut, watched on TV from his yacht.AFP via Getty Images
In a 2003 Golf Magazine interview, Mickelson mocked Woods’ clubs, which the golfing champion had helped design, as “inferior” and then paid him a back-handed compliment, saying he was the only player good enough to “overcome the equipment he’s stuck with.”

Woods’ response was curt. “Phil can try to be a smart aleck at times,” he quipped.

Even though the antipathy between the two men is well-known, Ryder Cup captain Hal Sutton paired the two together for the biennial Europe vs. USA contest in 2004.

“I felt like history needed it. I felt like the fans needed it. And, most of all, I felt like Phil Mickelson and Tiger Woods needed it,” Sutton said at the opening ceremony.

Tiger Woods has a charmed outing at the 2021 PNC Championship, where his team — including son, Charlie — hit 11 straight birdies in the tournament’s final round.USA TODAY Sports
But what started out as the Dream Team soon became more Laurel and Hardy as Woods and Mickelson sulked and scowled their way through two dismal performances, ending their partnership barely on speaking terms as the US fell to Europe in a humiliating home defeat.

“If it weren’t for the uniform, you wouldn’t even know they were teammates,” writes Harig.

Harig writes that Woods has strained relations most over the years, arguing that it could be Mickelson’s image as the “man of the people” he finds most galling.

“Nobody will say that Tiger hated Phil,” he writes, “but there was a strong dislike.”

At times, it seemed as though Woods enjoyed the spell he held over Mickelson. When Mickelson blew a golden opportunity on the final hole to win the US Open at Winged Foot NY in 2006, Woods, having missed the halfway cut, was spending the weekend watching the final rounds on TV from his yacht.

“Privately, Woods texted an acquaintance to get a sense for what happened,” writes Harig, “and derisively asked what body part Mickelson tripped over.”

To this day, Mickelson has never won the US Open — the only one of the four majors he has failed to claim.

Family man Mickelson holds the Claret Jug with wife, Amy, and children, Evan, Amanda and Sophia, after winning the 142nd Open Championship in 2013.R&A via Getty Images
Today, Woods and Mickelson enjoy a much friendlier relationship, which the latter attributes to the 2016 Ryder Cup, where Woods was a non-playing assistant captain and Mickelson a team member. “For once, the Tiger-Phil dynamic saw them on the same side, likely a more difficult leap for Woods than it was for Mickelson,” writes Harig. “He spent the better part of 20 years keeping Phil at a par-5 distance; now not only did they exchange phone numbers but they were also regularly texting each other to discuss strategy.”

Both men, despite their advancing years and issues off the golf course, remain the biggest draws in golf. That’s why they were only participants in 2018’s “The Match,” a made-for-TV, winner-takes-all contest over 18 holes at Shadow Creek in Las Vegas, which Mickelson won in sudden death, taking the $9 million prize.

In 2019, Woods won the Masters after a majorless drought stretching back to 2008 when he took the US Open with a broken leg, while Mickelson won the PGA Championship at the age of 50 — the oldest ever winner of a major title.

Woods and Mickelson play a practice round before “The Match” at Shadow Creek Golf Course in 2018.Getty Images for The Match
But they’re still gunning for each other.

On March 2, Woods won $8 million when he edged out Mickelson to score the PGA Tour’s inaugural Player Impact Program award and tweeted him, saying “Whoops.”

Embarrassingly, Mickelson thought he had already won it. “I’d like to thank all the crazies (and real supporters too) for helping me win the PiP!!” he wrote on Twitter, before realizing his mistake.