Caddy Confessions: Looping at St. Andrews

Mark Eglinton is a Scottish author and ghostwriter known for his collaborations with prominent figures across sports and entertainment.

With a talent for capturing personal stories and insights, Eglinton has worked on autobiographies and biographies that bring readers closer to the lives of both athletes and entertainers.

His expertise in storytelling adds depth, perspective, and provides unique insights into the lives of the subject. This makes his work engaging for both the most seasoned fans and newcomers alike.

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It’s the final Sunday of the 2006 Alfred Dunhill Links Championship in St. Andrews and Dennis Hopper’s goatee-encrusted face is gripped tightly in my friendly headlock.

“You sir, are a cinematic legend, did you know that? Did you?” I strain, breathing vintage Tattinger champagne directly into his eyeballs.

“Why thank you,” Hopper says, as I gradually ease the pressure on his trachea.

Seemingly appreciating the back-and-forth, Hopper wrestles free, shakes my hand, again, and swerves off to the hospitality tent bar—somewhere I’d been stationed for the previous eight hours, courtesy of a player’s badge given to me by a five-time Olympic gold medalist. For those few moments, my world and Hopper’s were one.

Allow me to explain. The Alfred Dunhill Links Championship is one of the last events of the European tour schedule, and perhaps the most unique. The Dunhill is the equivalent of the Pebble Beach National Pro-Am and it attracts a similar cast of celebrities: Bill Murray, Samuel L. Jackson, Michael Jordan. For the Old Course caddies, of which I was one for a while back in the day, the Dunhill represents not only the last decent payday of the year but also a rare chance to work a real tour event, with all the perks that can offer: hanging with celebs, scoring free gear, collecting decent tips, and more.

For us caddies, the Dunhill served as the culmination of six months’ hard work shepherding six-hour rounds with hackers from everywhere you can think of, each of them paying serious money for his or her trip-of-a-lifetime on golf’s most hallowed turf; asking touristy questions like “Gee, is that Norway?” the moment they caught a glimpse of any land across St. Andrews Bay; swearing blind that back home they could hit their 62 degree lob-wedge 125 yards into the wind; lying down flat on the green like an alligator to survey quadruple-breaking putts they had no hope of reading and far less of making; all the while, from the 12th tee onward the only thing that kept us going was the thought of an ice cold pint of Tennents sitting on the bar…paid for by our players.  

Throughout the season, some caddies would totally lose it, going AWOL for days on end, stumbling from pub to pub, muttering darkly in some corner about all the “scrap” or “filth” they’ve had to deal with lately—both terms caddiespeak for low-ability and low-paying golfers.

Depending on their lifestyles, caddies would have some cash in the bank to survive the winter or in some more extreme cases they would have wasted earnings away in the pub/betting-shop or in the service of chronic debt. Either way, many of the 50 or so hardcore caddies that work the Old Course would always emerge the following spring with hopes that the next would be the season that changed everything, while making grand proclamations like: “Soon I’ll be out of here.”

And so Dunhill week is all the more freighted. Desperate caddies would haunt the driving range, seeking any kind of bag. They would speculate—with almost no basis in fact—as to which fringe pro or glamorous celeb was without a bagman, with the hope that they’d find their way into that job.

I was a stealthier hunter. Here’s the thing: The key to getting inside the ropes at a major golf tournament is to look like you belong there. In practical terms, belonging meant wearing the right gear and saying the right things. This was the time for flashy rain gear, as Tour caddies wear rain gear whether it’s raining or not and so should pretenders. Next: sunglasses. No cheap gas station pickups, mind you: Oakleys were best – or at the very least fake Oakleys. 

Finally — and this was key in deceiving security guards — nod at people as if you know them. An upward head motion as I approached worked best…just enough to catch their eye. But no smile. I’d look earnest, as if I was going about routine business. I didn’t know them and they sure as hell didn’t know me, but that was part of the ritual.

The next step was always to access the practice area, the only place I’d be able to find a job. It wasn’t too difficult. A flash of my “OLD COURSE CADDIE” badge or even a Starbucks loyalty card was often enough to get waved through. Then I’d have entered a unique comfort zone, where grizzled tour caddies milled around the Titleist truck, sucking down coffee while discussing where they’d be next week. Since neither I nor any other local caddie would be anywhere but in St. Andrews next week, it’d be time to hit the practice tee to see who looked unsupervised.

A competitor without a caddie is often that way for a reason, so Rule No. 1 was to take a close look at the swing of anyone who was unattached and calculate whether your week of work would be worth the misery. If the ball is going sideways on the range, chances are it’ll do the same on the course (and you’ll get the blame).

On that fateful day at the 2006 Dunhill, my first potential meal-ticket was an ex-NFL superstar whose unorthodox but strangely effective swing was sending the range balls a respectable distance and in an almost straight line. I couldn’t help but do the math: He’s a Hall of Famer, so he’s got to have a bit of cash, right? I watched him hit a few more before moving in…

“Hey, man, how’s it going? You’re hitting it pretty good.”

“Hey, thanks—I’m doing okay.”

“Hopefully it’ll be a great week,” I said, the unspoken for me dancing in my head. “So, are you fixed up with a caddy?”

“You know, I think I had a guy lined up,” he mumbled, suddenly looking at something that clearly did not exist in the grooves of his eight-iron. “But I don’t really know what’s happening.” He looked a little sheepish, as if I wouldn’t believe him.

I didn’t believe him. 

We each knew exactly what was happening: I was not going to be caddying for him. But we went through this strange routine all the same.

“Oh yeah, here’s my card anyway. If you need me, give me a call, OK?”

“Sure, sure. Thanks man!” and with a handshake I left him. As I walked away, I watched as he put my card in the trashcan beside the tee box.

Rule No. 2: Do not kiss musician or sports star ass. It won’t get you the job and you’ll feel like an idiot.

A famous drummer was in the next practice bay, cutting up with someone who looked like a friend or maybe an agent, but not a caddie. Figuring that the cash could be good, I tried my luck with him, pretending we’d met before, ignoring the fact that he looked like he was chopping wood.

“Hey man! Good to see you again! How are you hitting it?”

He looked at me like I’d landed from another planet.

“Err yeah, it’s going good, going good. Just working on a few things,” he grunted, barely looking up between swings.

Despite thinking that he definitely should be working on a few things, I felt the urge to try and ingratiate myself with him—even though I expected him not to bite on it.

“Hey, I spent some time in Jersey a few years back,” I said, which had the benefit of being true, “and I got to be a big fan of the band. Even went to a few shows.” (I hadn’t.)

He didn’t respond; he only scowled. Because I was already committed, I asked the question anyway.

“Are you looking for a caddie for the week? I’m your man, if you are…”

“I’ll wait, I think. Listen, do you mind? I have to practice.”

He was—in the politest way possible—suggesting that I go away. No card. No call me. Just go away.

Oh-for-two. It was time to regroup with a coffee and hotdog at the Titleist van.

And then, good luck intervened. Someone on the driving range wanted some alterations made to his driver. I intercepted him on his way to the truck, where I stood looking like I didn’t care. But I did care. I cared deeply. My week depended on his being responsive to my polite, if intense, request as to whether he needed help for the tournament. 

“I’m on the tee in 15 minutes,” the guy with the driver said. “Let’s see how a practice round goes?”

At that moment I placed the face: He was a decorated Olympic athlete, albeit in a sport that does not garner widespread publicity. I hitched a ride with him on one of the courtesy golf carts, up the 1st fairway and past the caddie shack, where I was greeted by the frustrated faces of peers who did not have a job for the week. The caddie master didn’t look happy, either. Technically all jobs should go through him — that’s the unspoken rule.

“We’ll talk about this when all this is over, Eglinton,” he said from the window as I drive past, writing something down in a notebook.

“What does he mean?” my golfer asked.

“It’s fine — don’t worry about it.” 

And it was fine. I had a job for the week. What kind of job it would be was unclear. But I’d be working.

“Handicap?” I asked him on the 1st tee.

“My clubs…” he said with a wink.

Oh jeez.

“No really, what do you play off?”

“Twenty-four, but my friends say I’m better than that.”

Do they, I thought. As we all know, excellence in one sport often fails to carry over to the golf course.

He pulled out eight degrees of brand-new driver, price tag still on the shaft. I looked skyward and note that roughly 35 miles per hour of wind was howling from an easterly direction, over our right shoulders.

“You won’t need that,” I told him.

“I want to hit it; it’s new.” 

He addressed the ball awkwardly; this confirmed my doubts. 

“Keep this left side,” I told him.

The ball knifed away in a low, hard hook, going left—further left than I meant.

“How’s that looking?” he asked, still holding the finish.

“Well it’s not stationary yet. I’ll tell you shortly.”

The ball came to rest in a position not immediately clear from the tee. The driver was too much club, clearly, even for a golfer of this ability. But at the same time, there was no splash indicating that the ball had entered the Swilcan Burn. As we got closer, the reason for that became apparent: The ball was sitting on the bridge itself.

“What do you think?” he asked. 

“I think I’ve seen a few things out here. But I’ve never seen this.”

The ancient bridge, the site of many a tourist photograph, is constructed of stone worn as smooth as polished marble. You couldn’t get a ball to stay there if you spent all day trying to place it. Yet this guy had driven it there. Really, it was quite a feat.

“I want to play it as it lies,” he said.

“Can’t be done. And it’s a practice round. Pick the thing up and drop it back here.”

“I’m playing it…”

He played it, all right – and the ball struck the low retaining wall of the bridge, ricocheting sideways and backward at enormous speed in the general direction of someone’s car windscreen adjacent the 18th fairway.

“What do you think?” he asked as we got to the ball on the road.

“I’d give you a yardage but I’ve never been here before…”

This was going to be a long week.

The tournament draw sent us to Carnoustie for the first round, and the forecast called for wind and rain. Our professional playing partner was an aging and mildly corpulent inhabitant of the European Senior Tour. He was known for his impatience. The other pro in our group was an up-and-coming Englishman who had won twice on the European tour that year; he, too, was paired with an amateur. As arranged, I turned up at the Carnoustie practice range at 7:40 a.m. in almost total darkness. 

“How’s the course setting up?” my player asked.

“It’s setting up long and tough,” I replied, probably a little negatively.

“Car-Nasty, eh?” he said with a smile. Clearly he’d heard that moniker earlier in the week in the bar.

“Something like that, yes…”

The senior pro walked onto the 10th tee, where we were due to start, looking like he really didn’t have particular interest in being there. When his three-wood crept into a bunker down the right side, he shot a dark look at his baby-faced local caddie. 

“I didn’t think you’d reach that today,” the caddie said.

“Let’s just hit a long iron down here,” I told my guy in a futile attempt to get out on solid footing.

“No, I’m going with the big dog, baby.”

“OK, well remember what I said about not aiming too far left.”

He aimed miles left.

The ball started left and kept going left, into trees and gorse bushes barely discernible in the half-light.

“Where’s that gone?” he asked me.

“Nowhere good,” I told him. “Hit a provisional.”

“Nah, a man of your ability will find it, surely.”

“Hit a f---ing provisional,” I snapped, not wanting to hold up the course as he walked back to the tee. “Please.” In that moment, I felt our relationship change. I wanted him to do well, and that meant rather than building camaraderie, he needed to listen to the advice he was paying me to give him. But I needed to temper my frustrations and use my people skills.

We eventually found the ball, deeply unplayable, buried in the gorse. 

“OK, the round starts here,” I said. Pathetic, entirely unfounded positivity.

“I can reach from here,” he replies, eyeing a green 180 yards away, guarded by the Barry Burn.

“Forget it, put it in the fairway,” I said, handing him a nine-iron.

The old pro was giving us the stink-eye from across the fairway, having left his in the bunker. He walked off the hole with a five—we left with an eight. 

“We call that a snowman,“ I said on the way to the next tee.

“Why’s that?” he asked, looking at me like I’m insane.

Things didn't get any better during the second round on the Old Course. Halfway up the 4th hole, which shares a fairway with the incoming 15th, I noticed a caddie holding up a ball like he’d just drawn a winning lottery ticket.

“What on earth are you doing?” I asked him when I draw alongside.  It was a caddie I knew. He didn’t get let out often. He was wearing a baseball cap on his head that read PUGS NOT DRUGS.

“Whose is this?” he asked. “It’s not ours.”

“Yeah, well, why are you picking it up? This is a tournament. There are two fairways here.”

“Oh yeah, sorry.”

He dropped the ball and the young English pro, whose ball it was, appeared on the scene.

“Who was that clown?”

“Oh, some caddie who thought it was his golfer’s ball,” I said.

“Should he really be out here?” the pro asked.

“Probably not,” I told him. “But neither should a lot of them.”

We encountered another suspect caddie standing on the 11^th tee. He was a few weeks into his first season, having previously served time as a gravedigger. The tee was backed up two groups, a frequent occurrence on tournament days while groups navigate holes 7-11 – “the loop.” Admittedly, there was a lot of wind in our faces. But the par-3 11^th was playing, at most, 190 yards in the gusts. For most players, that’s not a driver. But the flustered ex-gravedigger pulled one out anyway and handed it to his celebrity boss with the proviso, “Don’t hit all of it.”

When the green cleared, the ball leapt off the golfer’s driver on an alarming trajectory. “Wrong club,” someone muttered.

I leaned over to my golfer—the ball still rising at it passes the green below—and said, “This might never come down.” There was, of course, an element of pleasure in seeing someone else commit such a radical “cuckoo”—the caddie term for a massive club miscalculation.

The ball didn’t come down, at least not in Fife. It landed every bit of a hundred yards beyond the green in the Eden estuary. 

“That wind changed,” the caddie told his man—an old caddie trick—before handing him a four-iron, a more appropriate club.

“Do they really let people like that caddie for money?” my golfer asked me as we walked up the next fairway. 

I nodded my assent.

“You’ve got to wonder why they do it all,” he wondered out loud.

As I walked with him, I realized he has hit on a feeling within me, and I winced at the thought of being implicated.

Why do they do it? 

Why was I doing it?

Turning 35 was the culmination of many things in my life. My father lost an agonizing five-year battle to rare condition called multiple system atrophy that produces symptoms similar to Parkinson’s disease. He’d worked hard all his life, made huge sacrifices for his family, and enjoyed the chance to do what he loved in retirement, but there was nothing to show for all the toil. I’d run a once-successful business that, because of a changing world, was no longer profitable. When the business folded I lost everything. 

For a few months I gathered whelk shells on Fife beaches to sell to a local shellfish dealer as a way to put food on the table for my two young kids. As I contemplated what to do with my life, I kept flashing back to what my English teacher at school used to say to me: “Eglinton, you should write for a career.” But he would invariably add, “Eglinton, you’re like the tide. You come in. Then you go away again.” (I rarely attended his class.)

But he planted a seed that had survived those 20 years. Lacking any career prospects, I had a once-in-a-lifetime opportunity: I was finally going to write. 

Caddying was a solid way to pay the bills while I pursued a writing career. It had been in front of my nose all along: I’d grown up on the Old Course, playing it hundreds of times. I knew aspects of its terrain that only a local could. I knew what the winds did to certain shots; I knew the putts that broke the opposite way they looked. 

Being a caddie, I realized, also afforded me something invaluable to an aspiring writer: The chance to further learn about human nature. I had always been a keen observer of people, going back to circulating my parents’ parties, serving drinks, crisps, and wisecracks before being sent to bed. I’d continued my studies in the pubs of Edinburgh, where I did more eavesdropping than drinking. Caddying was a chance to go even deeper; what other job presents a daily conveyor belt of disparate people with whom I’d be required to spend five hours? And they’d pay me for the privilege. 

Despite the frustrations, the utter madness of all the bad golf, the nonsensical caddie shack conversations, the absolute paranoia about tips, that odd mixture of being viewed as a seasoned expert and a paid servant, caddying on the Old Course was an incredible thing to do every day. And getting to the work the Dunhill felt like a validation of my expertise. It was one of the most important tournaments of the year, and I was part of it—alongside an Olympic medalist, no less.

Walking up the final few fairways, my player and I stopped grinding on the golf and chatted like friends.  Despite different backgrounds, I sensed we had more in common than I’d expected. Over four days we had drip-fed each other, unwittingly at times, some honest aspects of what make us the people we are. 

In those final few holes, we found common ground. He told me about how his life had played out, how he’d gotten to this point, and I reciprocated. We’d been thrown together randomly as boss and client, back at the Titleist truck, but those terms meant little in the end. Even though I would still be paid for my work, we’d come to understand each other. The golf had become a welcome sideshow for us both.

As we walked up 18 at the end of our four-day odyssey, he turned to me and said, “When I first met you, I had no idea what to expect. But you don’t seem like a normal caddie.”

“Thanks,” I said, instinctively putting a hand on his shoulder—the first time we’d made physical contact. “But I’ve got to ask: What is a normal caddie?”

“I suppose I don’t know. But I had a pre-conceived image, I suppose.”

“Of what?”

“Maybe somebody who drinks a lot,” he said, laughing. “And who doesn’t know what else to do with their life.”

We got to his ball, close to the railings down the right side of the 18th fairway—not far from the windscreen he hit a few days earlier,

“What now, boss?” he asked with a smile. “‘Keep it left,’ I suppose?”

“Exactly,” I told him.