I caddied for a top-25 player in the world at a PGA Tour event. Here's what it was like

Daniel Rapaport
Golf Digest

“The Text” came while I was asleep, as all my favorite texts seem to do. It was one of those messages you have to read a few times before you can convince yourself it’s actually real:

Got a question for you, pal … looks like I’m going to be playing AT&T. Would you want to caddie for me?

On one hand, this was a long time coming. Matt Fitzpatrick—always Matt to me, never Matthew—and I became friends during his 10 minutes on campus at Northwestern in 2013. (I graduated in four years; he pulled out after one especially cold freshman fall to prepare for some major tournament in Georgia.) Matt had won the U.S. Amateur about a month earlier and was the No. 1 amateur in the world. I had been following his rise closely because I was trying to walk on to the golf team, and the coach had communicated that there was only one roster spot open, and it was going to this British kid, Fitzpatrick. So, if I were to make the team, I’d have to convince the coaches that I was better than the best amateur golfer in the world. In related news: My dreams of playing for the team didn’t last long.

RELATED: A mini-documentary of the author's experience caddying on the PGA Tour is available in Issue 5 of the digital edition of Golf Digest. Download it now for free.

I’d be lying if I said I wasn’t looking for this Fitzpatrick fellow when I arrived on campus, and sure enough, I saw him eating alone in the dining hall during the first week. (He denies that he was eating alone, but trust me, he was full Steven Glansberg.) Being the generally shameless person that I was in my teenage years, and the golf perv I still am, I plopped next to him and immediately began babbling about all things golf. Miraculously, he didn’t run away, and a friendship was born.

RELATED: Matt Fitzpatrick on why he thought he would be the last player to ever play with Tiger Woods

We kept in loose touch after Matt left school. During his time on the Challenge Tour, I’d reach out every now and then to make sure he was finding something to eat in places like Kazakhstan. After he got his European Tour card, he came back to Chicago to visit semi-regularly, so I’d see him once in a while, but our relationship basically consisted of my “good luck” and “congratulations” texts and, on good days, him blessing me with some tour gossip: This guy has got the chipping yips. That guy has a new girlfriend. That sort of thing.

That all changed in March 2018 when Sports Illustrated granted my wish to move from a general-assignment position to the golf beat. I made it out to a few tournaments that year, and Matt and I would have dinner and walk a few practice-round holes together. Our correspondence became more frequent: texting, Instagram direct messages, etc. Toward the second half of 2018, when he had cracked the world top 50, we planned for him to stay at my parents’ house in Los Angeles during the Genesis Open at Riviera. Despite not yet being a PGA Tour member, he was optimistic he’d receive a sponsor’s invitation.

He was wrong. No invite came, but he’d already booked his flights and was planning on taking the tour charter from L.A. to Mexico on Sunday night for the WGC event there, so he came anyway. Teed it up in the Monday qualifier; missed by one.

This was bad news for Matt, who now had a week in L.A. with nothing on his schedule. This was great news for our friendship, which blossomed over the next seven days. He showed up to my normal Sunday-morning game at Brentwood Country Club, dressed head-to-toe in full PGA Tour attire. On his first time seeing the course, he shot a seven-under-par 65 with a three-putt and a water ball. We went out to a swanky Italian restaurant and ran into Sergio Garcia, whose wife asked me if I, too, was a golfer. (Only an amateur, I said.) Matt complained about the traffic all week, but he loved L.A., though he might never admit it. He finished T-27 the next week in Mexico, then took solo second at Bay Hill in his next start, all but securing his PGA Tour card for the next year.

Before that three-week stretch, I had a semi-friend who was trying to get his card. After that stretch, I had a dear friend on the PGA Tour.

I had joked about the possibility of me guest-caddieing but never expected anything to come of it. Matt is the ultimate professional and isn’t the type to waste a week of competition just to do a friend a favor. Plus, he started working in January 2019 with Billy Foster, a legendary caddie who looped for Seve Ballesteros and helped Lee Westwood reach World No. 1.

My window cracked open when Matt climbed inside the top 30 in the World Ranking in the fall of 2019, putting him on the cusp of qualifying for the Hero World Challenge in the Bahamas. I said to Matt that if he played well enough to qualify for that exhibition, I should get to caddie for him.

He didn’t say no. Billy would be enjoying time off with his family, and Matt was second alternate, so he didn’t want to make Billy fly across the Atlantic at a moment’s notice for one tournament. I was already going to be there covering the event for Golf Digest, so a moment’s notice was no issue for me. A week before the event, Matt finally said it: If he got in, I was on the bag.

Still, we needed two withdrawals for that to happen. I received a text from Matt saying, “One more to go!”—suggesting one guy had pulled out, right before I received a push notification from the PGA Tour saying, “Dustin Johnson has withdrawn from the Hero World Challenge.” I thought we were in, but Matt had learned of DJ’s withdrawal before it became official, so the text and the notification were both talking about DJ. Chez Reavie took the spot. Bummer. But the caddie door was open now.

One month later, The Text arrived. I know other writers have gotten the chance to caddie for a touring pro. But I was about to caddie for a top-25 player in the world, for a full week, at an iconic PGA Tour event. That I somehow refrained from tweeting the news until the Monday of the tournament was a miracle of self-restraint.

<div class="caption"> Rapaport and Fitzpatrick at Pebble Beach’s 18th during the opening round, when PGA Tour Live broadcast their group’s play to families and golf’s masses. </div> <cite class="credit">J.D. Cuban</cite>
Rapaport and Fitzpatrick at Pebble Beach’s 18th during the opening round, when PGA Tour Live broadcast their group’s play to families and golf’s masses.
J.D. Cuban

Practice Prep: Math is involved

I flew to Monterey on Tuesday morning of tournament week. The plan was for me to walk Monterey Peninsula Country Club on Tuesday afternoon before Matt arrived Tuesday night. Then we’d play a practice round on Wednesday at Spyglass.

I didn’t have a yardage book as I walked MPCC, so I took a ridiculous amount of notes, all of which were made obsolete when I got my yardage book the next morning. I wrapped up at MPCC and met Matt’s manager for dinner that night in the village of Carmel. We got back to the Airbnb—a quaint-as-can-be cottage in Carmel—and shut the lights off for an early night. In our haste, we almost forgot to leave the door open for the boss, who would be arriving around 11 p.m. One should never forget to leave the door open for the boss.

The next morning we packed up the TrackMan—always be extra careful with the TrackMan, cuz that thing ain’t cheap—before breakfast. With the sea-level elevation and damp air of the Monterey Peninsula, launch-monitor sessions before every round are extra critical for calibrating carry distances. As we left the table and headed to the door, there was an awkward silence as no one made a move toward the bag. Then I remembered, That’s on me this week. I got my first taste of the 45ish-pound behemoth as I carried it to the Lexus courtesy car. I’d find that if I stretched each night, I wouldn’t wake up too sore.

Matt made sure we played the practice round alone, possibly because he prefers going at it solo, but more likely to give me a chance to get my bearings without worrying about anything else. What a nice boss!

My first order of business was figuring out how we’d calculate yardages. There’s a surprising amount of math involved. It’s not difficult math, but there’s a lot of it, and it needs to be done quickly and correctly. The process starts with the tee shot. The tour yardage book gives you a number to every sprinkler head, as well as how many yards uphill or downhill it is. But the yardage is given from the back of whatever tee the person who made the book thinks will be used, so you have to pace off how far the markers are from the back of the box. If they’re using another tee box, that’s another layer.

The more crucial calculations come with the approach shot. The book will list every sprinkler head out there, and the sprinkler heads show a number to the middle of the green. But pros aren’t concerned with this yardage. So you find the nearest sprinkler—say, in this case, it reads 140—and check the book. The book tells you that from the 140 sprinkler, it’s 124 yards to the front, and it will also list the slope. Say it’s six yards uphill—it’s playing 130 to the front edge. You then consult the daily pin sheet, which tells you how many paces on the green the flag is. Say it’s 14 paces on. Now we’re at 144 to the flag. But we’re not trying to land it at the flag. Say we want the ball to pitch four paces short. Now we’re back to 140. On to the wind. Say it’s a bit into the fan. Matt thinks it’s playing five yards more. Now we’re at our number: 145. Last calculation: a start line and a finish line. Then, finally, it’s go time. All that in less than 30 seconds.

I thought I had the hang of it all until we reached the ninth hole, an uphill par 4 that turns slightly right. Matt hit his drive in the middle of the fairway—it’s hard to overstate just how straight Fitzy hits it—and asks me, and me alone, to get the yardage. A test! I ran through the numbers quickly and confidently. I communicated to him that it was playing 158 with a hair of wind in the face, a perfect 8-iron. After he struck the approach, it was clear the ball needed to sit—quickly. Get. Down. Now. It didn’t, and it pitched on the back edge of the green, a solid 15 yards past the pin. He then gave me The Look. Every caddie knows The Look. It’s when your player stares at you piercingly, and you both know that you have just screwed up massively, and someone better just say something already. I looked back down at the pin sheet, and sure as hell, I was looking at the eighth hole, not the ninth.

Fitz found it in his heart to forgive me, and I hit my stride by the back nine. There was hardly a soul at the course besides the players and their caddies. The best way I can describe that stress-free afternoon is through a casual interaction we had with Patrick Rodgers, who was walking back toward the 16th tee when we passed him. “How we doing?” Matt said.

Rodgers looked around a second, at the towering pines and the pristine bunkers and the shadows blanketing the fairways, then looked back at Fitz: “Living the dream, man.” On tour, everyone is all smiles on Wednesdays.

RELATED: You can download the latest Golf Digest digital edition for free

We finished the practice round and headed into Carmel for the first of four consecutive Italian dinners. (The boss likes Italian, and the boss pays for dinner, so Italian it is.) It was there that we found out our pairing (Matt Kuchar) and pro-am partner: Eddy Cue, a legendary Apple executive and, it turns out, a super-fun guy. It was also at dinner that I discovered that our first round, at Pebble, was going to be featured on PGA Tour Live, meaning my family and friends could watch every shot of my first round caddieing on the PGA Tour. Storybook stuff.

I hardly slept, yet felt extremely fresh when I rolled out of bed around 6 a.m. Here’s to you, adrenaline. It was still dark as we loaded the car, cranked the heat up and made a silent drive to Pebble. Too early for conversation. I go to a number of PGA Tour events and get inside-the-ropes access, so seeing all the golfers wasn’t much of a rush. But man, it was hard to keep a poker face as I stood in the buffet line between Peyton Manning (partnering with Luke Donald) and Aaron Rodgers (Max Homa).

As we munched on our toast and eggs, Fitz asked me if this was my first time caddieing for a pro. No, I told him. I used to loop for a guy from my club who played a couple seasons on the then-Nationwide Tour, now-Korn Ferry Tour before he gave it up to become an app developer. I told Matt the story of what happened in a 2010 U.S. Open sectional qualifier. My player, Danny Wax, had shot three-over 74 in the first round of the 36-hole day, essentially putting him out of it. We went for every pin in the second round, and it worked. After holing out from a greenside bunker for birdie on 17, he was eight under for the second round heading to 18.

I was 15, so perhaps I deserve some leniency, but I committed what amounts to a Caddieing Felony. I turned to Danny and said, “Looks like we’re getting ourselves a course record today.” He hated the comment, pushed his drive into the trees and made bogey. He did set the course record, but he also missed a playoff for the U.S. Open by one shot. So that was the last story Matt heard before we headed to the course. He laughed, then he stopped and stared into my soul: “Don’t do that.”

<div class="caption"> Our writer wasn’t surprised at the physical grind of caddieing in a tour event, but rather how exhausted he was mentally. </div> <cite class="credit">J.D. Cuban</cite>
Our writer wasn’t surprised at the physical grind of caddieing in a tour event, but rather how exhausted he was mentally.
J.D. Cuban

The ups and downs of a paycheck

We’ve arrived at the tournament part of this story, which I’ll keep brief. Matt started with a solid one-under 71 at Pebble, then followed it with a two-under 70 at Spyglass. I could sense his trust in me growing. We discussed start and finish lines on every tee box. We went back-and-forth on club selections. And he even called me in for a few reads. “Don’t get excited,” he said, always one to keep me in place. “It’s just because you grew up on Poa.”

We were in a great position heading into Saturday at Monterey Peninsula, the easiest of the three courses. Yet we found ourselves one over for the day and one shot outside the cut line on the 15th tee. Unbothered, he told me we needed only two more birdies and we’d be fine. “Screw two, let’s get four,” I said. Optimistic. Naïve. He laughed. Then he proceeded to go nuclear—birdie, eagle, birdie, par to finish. That’s four shots, for those of you counting. A three-under 69 had us T-20 entering Sunday. Read: A guaranteed paycheck for this fill-in caddie.

We played the first eight of the final round in even par, which had us creeping up the board on a brutally windy day. The last 10 holes were a disaster. We made triple on 9, bogey at 10 and double on 12, and just like that, any possibility of a solid finish vanished. It’s funny—when you’re six over for the day through 12 holes, the mind wanders to what could have been done differently: We could have hit 9-iron on 9 instead of wedge, I could have said something different on 10 tee, we could have started that tee shot on 12 more right. To what you learned: Putts really do miss because of bumps, pros hit their 3-woods so damn high, Matt Kuchar gets more out of his game than anyone I’ve ever seen. And, I must admit, to dollars and cents: How much does one make for finishing 58th?

To Fitz’s enormous credit, he did not get all pissy and quiet—only a little pissy and quiet. After he hit the fairway on the par-5 18th, we had a brief discussion on whether to go for it. It would require a punch-draw 3-wood, under the tree in the fairway, with Stillwater Cove looming down the left, begging for a ball. Mid-deliberation, Matt goes, “Well, we do have to protect the lead.” We both laughed.

He did go for it, found the left bunker, then played a nice, long bunker shot to 14 feet and … three-putted. He signed for seven-over 79 and finished T-60—good for $17,472. Fitz, because we’re boys but also because he was staying at my house the next week, generously paid me as though I was full-time: 8 percent of winnings, which was just under $1,400—it would have been 10 percent for a top 10, we’d agreed—plus a healthy flat fee for the week. Tying for 60th wasn’t what I had in mind, but the sum that came through via direct deposit was still the most money I’ve ever made for a week in my life.

Players always talk about how “mentally tired” they are after a tournament, but I never understood what they meant. I do now. This was the most emotionally invested I’ve been in anything since high school sports. I was nervous as hell on the first tee every morning. I lived and died with every birdie putt. I cringed as he prepared to play a tricky flop shot, and my eyes got huge as I saw an approach fly directly at the flag. I buzzed as we started making birdies, and cursed as we started making bogeys. I was the happiest guy in the world after our Saturday back-nine flourish and virtually inconsolable (just ask my girlfriend) after a bitterly disappointing Sunday.

As I headed to the airport on Sunday evening, I just felt … spent. Pooped. My brain was tired from caring so damn hard for so damn long. I had the week of a lifetime, and I absolutely want to caddie in many more PGA Tour events, but let’s just say I wasn’t too upset to be back to the writing grind for the Genesis. I spent that week at my parents’ house, and Matt did as well. I slept in a bit Monday morning, sipped coffee, hung out with my dogs, wrote an article and worked on a few others, and just enjoyed not being a thousand-percent invested for an entire afternoon. I needed a break.

And Fitzy? He headed to Riviera first thing in the morning for a 9:20 pro-am tee time.

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