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The Tiger Woods vs. Phil Mickelson Prop Bets We Actually Want to See

The details of the reported $10 million showdown are still being ironed out, but that won’t stop us from placing some fictional cash on Phil putting a moving ball, or the number of side bets that will be made during the round

Getty Images/Ringer illustration

Ever since Golf Magazine reported last week that Tiger Woods and Phil Mickelson are ironing out the details of a one-on-one, $10 million, winner-take-all match play event, the golf world has been in a tizzy. Scouting reports have been drawn up, other pros have weighed in, and now you can even make prop bets on a match that, as of yet, doesn’t even have a date. But the existing props are just a little too bland, a little too standard for a showdown that will have this much history surrounding it, so the Ringer staff decided to come up with some of our own. Here are the Tiger vs. Phil prop bets we actually want to put money on:

Odds That Phil Putts a Moving Ball: +2500

Riley McAtee: Running after a ball and giving it a quick whack to prevent it from rolling down a hill and off the green—which is something we’ve all done, don’t kid yourself—in a professional golf tournament is some baller stuff. So when Mickelson did that at last month’s U.S. Open, I cheered him. Phil was already out of contention, and the Shinnecock Hills course was so difficult that it was nearly unplayable, even for golf’s elite. Mickelson’s putt was as much a time-saver as it was a statement: You didn’t take this golf course seriously, so why should I?

But golf etiquette purists blew their tops, and Phil apologized, which ruined everything. Now’s his chance to reclaim that IDGAF attitude in a contest with slightly more limited stakes (just $10 million). It’s perfect. I just hope I can make some money off of betting on him to do so.

Odds That Bones and/or Steve Williams Make an Appearance: +4000

Megan Schuster: Tiger and Phil have both had some legendary caddies over the years, aaand some legendary falling-outs with said caddies. Woods and Williams were together for 12 years before Woods stunned both Williams and members of the golf community by letting the caddie go back in 2011. And last June, after 25 years on Phil’s bag, Jim “Bones” Mackay announced that he and Mickelson had “mutually decided to go our separate ways.”

All parties have seemingly moved on: Mickelson hired his brother, Tim, to take over his bag duties; Tiger brought in Joe LaCava, former caddie to the likes of Fred Couples and Dustin Johnson; Williams caddied for Adam Scott until late last year, and has announced that 2018 will be his last year carrying a bag; and Bones joined the NBC–Golf Channel broadcast crew in an on-course reporter role. So it’s unlikely that there’s any reunion in store for these pairs. But still, for one unofficial match play event, we can dream—this showdown wouldn’t really feel complete without a Woods-Williams fist-pump-high-five combo, or an incredible read from Bones.

Number of Side Bets Made During the Match: Over/Under 0.5

Danny Heifetz: Phil Mickelson once sank a 14-foot putt on the 18th hole of match play with $1,600 on the line after Paul Azinger told him to, “Putt it, bitch.” Another time, Phil got so deep into Keegan Bradley’s head on the back nine of a match that Bradley swore off playing with him for a full year. And once, in the clubhouse at the NEC Invitational, Phil bet Mike Weir $500 that Jim Furyk would chip in a bunker shot. Naturally, he won. Mickelson doesn’t like to bet on golf. He likes to golf so he can bet.

Tiger and Phil have plenty of money on the line here already, but there’s certainly room for some side action: one-hole wagers, farthest-drive bets, and straight up “you will not make this putt” trash talk. Imagine if this match comes down to the 18th hole—or, my God, the final putt—and Phil dares Tiger to double down, with the winner sailing away on Woods’s yacht? Therefore, my ideal prop bet is a bit meta. “How many side bets will Tiger and Phil make during this match? O/U 0.5.” This would go down as the most degenerate gambling bet I can think of: a prop bet about other prop bets.

Odds That Both Guys Will Wear Nice, Sensible Golf Shirts: +7500

Katie Baker: On the Tuesday before the Masters, Phil Mickelson and Tiger Woods displayed their truest selves. Breaking out beyond the traditional confines of the classic golf polo shirt, Tiger donned his trusty neck-elongating blade collar while Mickelson allowed his inner Infiniti salesman to thrive. There was a lot to love about Phil’s ’fit that day. Using a tiny bespoke logo of oneself in oafy victory formation to hold up one’s pants remains a legitimate inspiration, though it paled in comparison to wearing a work shirt (?) bearing a “workday” logo, the equivalent of wearing the Steely Dan concert shirt to the Steely Dan show. As Tiger pointed out, the only thing missing was a tie. I can’t wait to see what these guys show up in when that sweet, sweet novelty made-for-TV exposure is on the line.

Number of Times Patrick Reed Will Try to Insert Himself Into the Match’s News Cycle: Over/Under 2.5

Paolo Uggetti: We’ve already got one! On Wednesday at the Scottish Open, Reed was asked about the matchup and he downplayed the excitement surrounding it by critiquing one specific aspect. “I would pay a little bit more to watch it if it was for their own money, for sure,” Reed said. “I’ll be curious to see it because I feel like one match, 18 holes, not your own money, it’s just kind of an exhibition.”

Of course it’s an exhibition, but that doesn’t take away from the fact it will be the most anticipated golf exhibition in ages, my guy. And yes, if Tiger and Phil put their own money on the line, it would be a different kind of tournament altogether—Tiger might be cursing to himself by the sixth hole, and Phil might throw a club. But that wasn’t Reed’s only suggestion for this match that totally doesn’t include him.

“I think it would be pretty cool if it was at night, like a three-round knockout,” he said. “Have old school [equipment], persimmon woods and balata balls, and then put them in their normal stuff and play a round at night. Have fun with it.”

I’m sorry, what? Reed’s a Masters champion now, so I’m taking the over here. Who knows, he could even end up speaking to the media about this tournament more than Phil and Tiger combined.