What it’s like to play in the Sentry Pro-Am (and why it might be the best pro-am experience on the PGA Tour)

I made birdie at 18, my pro was Sepp Straka and my team didn’t win.

KAPALUA, Hawaii – I made birdie at 18, my pro was Sepp Straka and my team didn’t win.

Now that I’ve gotten the answers to the three most common questions I’ve had from friends on hearing I played in the pro-am of the 2023 Sentry Tournament of Champions allow me to tell you what it was like playing in what just might be the best pro-am on the PGA Tour – especially now that the American Express and AT&T Pebble Beach Pro-Am have been watered down to fewer days and no longer have their celebrity appeal.

Call it my first hot take of 2024 but the Sentry Pro-Am starts with some pretty electric ingredients – a star-studded field of winners and anyone who qualified for top 50 on the FedEx Cup point standings in the preceding year coupled with the other star of the show – Kapalua’s Plantation Course – in one of the most beautiful settings for golf and you have the makings of a delicious recipe.

Before we go any further, let’s just take a moment to reflect on how insane it is to think that regular golfers can fork up some coin – some serious coin that I hear starts around $10K and is dependent on the hospitality package you pick – but in doing so be allowed to play the same course that a field of 59 of the most successful golfers in the world from the previous season are going to play the next four days for $20 million and you’re going to play alongside one of them (actually two as of this year — more on that later). What other sport can you do that? [Editor’s note: Golfweek was a special invite by Troon Golf, which manages the courses at Kapalua, and Golfweek made an exception to its policy as it was the only opportunity to play the Plantation Course during our visit for a separate travel story that was part of the assignment. We made a charitable contribution to a local non-profit, Spare for Change, which recycles donated golf clubs and distributes them to new players.]

On Tuesday, beginning as early as 8 a.m., participants began showing up at the Kapalua Golf Academy to pick up their tee prize. Every pro-am gives out some swag but this was next level. Last year, your gift bag began with a portable speaker and a TaylorMade driver head cover. From there, it was a veritable choose-your-own-adventure. In one room, you decide whether to get fit for a TaylorMade Stealth2 driver or custom-made jeans from Delta. Then you explored the rest of the Academy where you chose two of the following from Hawaiian favorites – Tommy Bahama apparel, Maui Jim sunglasses, Olukai shoes and sandals and this year Aloha Collection Bags – or you could go on a whale watching expedition or snorkeling trip – and if you were a conservationist or just had a big heart you could plant a Koa tree in the Pu’u Kukui Preserve. In short, really nice mix of swag between golf stuff and stuff that screams Hawaii. The food truck parked outside was a nice touch. During the day, participants get to play in the Am-Am at Plantation’s Bay Course, an Arnold Palmer design which is every bit as scenic and possibly more fun to play. I had to skip this round to do my day job but everyone I talked to said it was the perfect warm-up for the main event.

Mark Rolfing served as emcee of the 2023 Sentry Tournament of Champions pro-am draft party at Kapalua’s Golf Academy. (Adam Schupak/Golfweek)

That evening, pro-am participants met at Taverna Restaurant and the Academy’s putting green out back with NBC/Golf Channel’s Mark Rolfing serving as the emcee of the Draw Party. I met my team for the putt-off. This is what sets the Sentry pro-am experience apart. Thirty-two teams of three players were broken into pods of four and you had a putting contest to determine the drafting order to select one of four pros. Each player got to hit one putt from about 40 feet and the closest putt from your team determined your pick. My pod of four pros consisted of: Jon Rahm, Max Homa, Mackenzie Hughes and Sepp Straka. Not too shabby. My team got to putt last but it didn’t give us an advantage because you didn’t know how good or bad the other teams had done, couldn’t take a practice putt and you had to face the other way while your opponents took their turn, so, no help with the break or speed. We could tell by the audible reactions that someone nearly holed it. When my first partner hit his putt barely halfway, I knew we were in trouble. My second partner hammered it and still was 8 feet short. It was all up to me and I did get it to the hole but yanked it 4 feet left. I figured, OK, we’re not getting Rahm but maybe Homa. Nope, we were dead last and ended up with Straka, the burly Austrian with the Georgia accent, who would go on to have a pretty sweet year that included a pick to Europe’s winning Ryder Cup team. As I told him the next day, we were picking him first had we made the putt.

You can’t do this putting contest format with a pro-am at a full-field event – it would take too long – but it’s perfect for this limited-field event and is predicated on golf skill not just luck – most draw parties tend to have a lottery process and often the marquee names are reserved for the bigger sponsors. The food at the party after the putt-off was prepared by two-time Maui Chef of the Year Taylor Ponte and was outrageously good and the bar was open but I assume that is standard fare based on attending a few of these shindigs along the way. ESPN’s Chris Berman joined me for a glass of wine while I enjoyed some tuna poke and having grown up on his nicknames, 2-minute drill of highlights and calls such as “Back, Back, Back, Gone!” that was a rare treat. He’s a regular and The Kid, Ken Griffey Jr., also held court adding just enough celebrity buzz to the occasion.

Night putting at the 2023 Sentry Tournament of Champions draft party. Baseball legend Ken Griffey Jr. lines up his putt at the draft party. (Adam Schupak/Golfweek)

That night, I kept waking with anticipation to play in my first PGA Tour pro-am. That morning, I had a story to file so I wasn’t able to soak in the all-access pass at the range and the feast of food at the VIP tent but more than one tour pro who has had a beef with one of my articles along the way took great pleasure in critiquing my putting and short game on the practice green. I guess I had that coming to me, but for regular Joes I have to imagine it’s an unforgettable experience to rub shoulders with the pros.

Sentry tournament director Max Novena tells me they added a few new wrinkles to make the event even better this year. Most notably, with a larger field they instituted the nine-and-nine format popular at many other Tour pro-ams, where participants get to play with not one but two pros, who tag in and tag out at the turn. Pros and cons: if you don’t like your pro because he’s not helpful reading putts and disengaged, you may luck out with a more affable, charismatic pro who gets that you’ve ponied up big time for a special occasion. But you also don’t get as much quality time to create a lasting relationship, which can happen over 18 holes. I learned more about Straka, who had his twin brother caddying for him that week, during the wait on the tee than I ever have in one of his few press conferences in the media center. I had one beef with my pro-am experience – we basically played the red tees to avoid a six-hour round. That said, it was fun to hit the famous downhill 18th, measuring 677 yards for the pros, in two with a gap wedge. I usually leave out that we played the hole from 200 yards up when recounting this story.

When the round ended, we convened at a VIP tent and enjoyed a celebratory beverage or two. Not even two squalls during our round, the only liquid sunshine I experienced on my entire trip, could dampen my mood, and the rainbow over Kapalua made it worth it. Playing the course before the tournament only increased my appreciation for Jon Rahm’s closing 63 to erase a six-stroke deficit and win the Sentry on Sunday.

This year’s pro-am experience wrapped up with an awards party at Merriman’s Kapalua, which was my favorite meal of 2023. The setting on the point of Kapalua Bay looks like a movie set or a Zoom call backdrop – it has to be fake. But no, it’s so majestic that while my wife was snapping a family selfie, a guy to our right dropped to one knee and proposed to his girl. (She said yes!)

And if you ever get a chance to play in the Sentry Pro-Am you better do the same.

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