Confessions of a Long Island private club caddie: 6 stories from the bag

The most important job interview of my life lasted less than five minutes.

“So,” JEFF CULLINAN said, an eyebrow raised. “Do you like golf?”

We were inside the pro shop at the Rockville Links Club, a small Long Island country club I hoped to earn summer employment after my freshman year at Syracuse. I’d heard about the caddie program at The Links (capital-T, capital-L) from a family friend who happened to be a member and was willing to pass along my name. I was 18 and breathtakingly naive; Cullinan was a wiry man in his fifties and armed with the kind of instantaneous people-reading skills that come from a lifetime plied in the hospitality business.

Because work as a caddie is gratuity-only, we’d each entered this job interview with much more to gain than to lose. If I could pass the minimum brain-activity threshold, Cullinan could win three ways: first, he could make my member-friend happy by giving me the job; second, he could add another body to a caddie roster that was, like most caddie rosters, dependent upon the shapeshifting whims of a group of social outcasts and bratty kids; and third, he could achieve those goals while promising me, a kid from out of town with few connections, strikingly little in return.

It was a mutually beneficial situation, which was a good thing, because we both knew I was full of it.

“I love golf,” I said, repeating my rehearsed line from the car. “I’m an 18-handicap.”

To an idiot teenager with a limited worldview and a still-developing frontal lobe, this answer seemed like a means to an end. To a caddiemaster responsible for keeping his yard bullshit-free and his caddie program functioning, the follow-up was too obvious.

“An 18-handicap … what do you usually shoot?”

That’s where I stumbled. I wasn’t an 18-handicap, I didn’t truthfully know what that even meant, and my house of cards came tumbling down. But Cullinan hired me anyway, handing me a green caddie bib from the storeroom and instructing me to return the following day at 6 a.m. for my first shift as a caddie. I returned the next morning and every summer morning for the next four years, skipping only the days when my indoorsy summer gig (an internship in sports media) demanded it, and slowly climbing from the bottom of the totem pole to somewhere slightly above the mushy middle.

I was not always a very good caddie; it took time to learn the craft and I succumbed too often to a nervous tendency to fill silence with conversation. But it did not matter. I was smitten. The outdoors, the exercise, the grass, the camaraderie, the competition, the cash — I couldn’t get enough.

I was in love for the first time, and I knew it almost immediately.

***

My first day on the bag came with KEVIN, one of the elder statesmen of the caddie yard. Kevin, an army vet, had taken well to his combat training, and now carried the same militant focus to the contours of life on the bag. A firm but gentle giant, he was one of three Kevins in the yard in the summer of 2016. It was a clear sign of his standing in the hierarchy that he emerged the only one without a nickname. He was just Kevin, and he was the perfect man to teach a teenager to loop.

He was patient and kind all afternoon as he showed me the finer points of caddie life. I’d like to think I absorbed a lot from his wisdom that day, but I know for certain I was listening when he cut me off halfway through one too-long anecdote.

“There are three commandments to life as a caddie,” he told me bluntly. “The first is show up. The second is keep up. And the third…?”

He paused for dramatic effect.

“Shut up.”

***

In a strange twist of fortune, my first loop at The Links led to my first regular, CHRIS HECKMAN.

Chris — or Uncle Chris, as I have called him for nearly my entire life — was my hook into caddie life, but he was never supposed to be a fixture of it. When he passed my name along to Jeff the caddiemaster, he specified nicely that he was happy to help me land a job, but I would be on my own to find loops.

I’m not sure what I did to change his mind, but I do not say lightly that he financed a significant portion of my college beer fund. I looped for him for four years at The Links’ high holiday, the member-guest, and spent no shortage of afternoons listening to his piercing analysis on any number of topics in the golf world.

Uncle Chris was a Wall Street honcho in a past life, but his enthusiasm for golf came straight from the earth. In many ways, he was the archetype of membership at The Links: A club that placed golf’s role as a community good much higher than its reputation for elitism. His closest friends at the club — like the steadiest, most Statler-and-Waldorf-adjacent golfers I have ever known, PAUL NASTRO and KEVIN BERRY — were the children of a blue-collar Long Island town named Valley Stream. Uncle Chris’s knowledge for golf was all passion, and completely contagious. I also do not say lightly that a portion of my own love for the sport comes from him.

I still remember the last conversation we had before I left The Links, when I told him I was thinking about trying to get a job as a golf writer. He laughed.

“Really?”

Four years later, when I played Augusta National as part of the Masters’ annual lottery for golf writers, Uncle Chris was one of the first people I talked to. It was a special day for me, but in a funny way, I felt it might have also been a special day for him.

***

My first real loop came two days after my interview, a Saturday morning on the bag of a woman we’ll call JANE.

I’d been in the yard for nearly eight hours by the time my name finally got called for Jane’s bag, leaving ample time for the steady churn of performance anxiety. When Jeff called me from the caddie yard, I practically jogged out to the bag to shake Jane’s hand.

As I’d been instructed the previous day, I pulled Jane’s driver and waited to hand it to her from the side of the first tee box. As she neared the bag, she asked me to remove her driver’s headcover. I complied as quickly as I could, whipping the driver around to pull the cover off just as Jane crouched over her bag to grab a golf ball.

The leather was nearly in my outstretched hand when I felt the butt-end of the driver make contact with something solid. I looked down in horror to see Jane sprawled out on the ground, clutching the side of her skull. I tried apologizing, but it was no use. She was furious — and she hadn’t hit a single shot of a round that would stretch 5 hours and well over 125 recorded strokes.

Her head was fine in the end, but my ego never recovered.

***

One morning, Jeff found me in the caddie yard and sent me for a loop with a man named JIM TOMLIN.

I knew Mr. Tomlin. He was one of the club’s friendliest faces, but he was important to me for another reason: He served on the board of the Long Island Caddie Scholarship Fund. I had three years left at Syracuse when I started at The Links, but the cost of tuition had already proven a significant burden to my family, which was still recovering from the fallout of the 2008 financial crisis. The LICSF was a significant opportunity, promising $5,000 in tuition expenses to a handful of lucky recipients across Long Island’s caddie programs each year.

After our round ended, I learned that Mr. Tomlin would be happy to vouch for me to the LICSF, and within months, I was a proud caddie scholarship recipient. I spoke at the annual scholarship gala about how I’d come to learn a secret about golf from my rounds with Mr. Tomlin and many others: The sport was the great connector.

“In my career in sports, I hope to keep sharing that message,” I said then.

I still do.

***

STEVE DiMARE was mononymous at The Links. To those who knew him and those who did not, he was just DiMare — a phrase that, in the Long Island dialect, could appropriately be delivered as “Da Mayor.“

For the first six months I worked at The Links, I thought Steve’s nickname was The Mayor. Steve was the club president. He was also beloved by the members, the caddies, the wives, the kids, the clubhouse staff, his family, and everyone else with the good fortune of crossing paths with him.

Deeply tanned, quick to laugh, and usually found with a cigar tucked between his teeth, DiMare carried an easy warmth. He was a self-made man — part of a dying breed of New Yorkers who amassed impressive fortunes on the back of grit and sheer force of will — and he carried himself with the confidence of an individual who could fix most problems with a pair of phone calls. Late one August, I found myself carrying two bags in one of his foursomes and finally understood why.

I was fifty yards up the second fairway serving as a forecaddie for DiMare’s tee shots when the other caddie in our group, a nice guy nicknamed FISH, tripped. Then, somewhat suddenly, Fish gasped.

“Oh shit.”

I looked at Fish’s feet to find the soles of his shoes had vanished. In a manner never seen before or since, the soles had simply removed themselves from the footbed of his sneakers, leaving Fish to limp mostly barefoot down the second fairway. Without another pair of shoes handy, he was screwed, staring down a long, hard, painful walk or the unthinkable prospect of walking off.

“Only seventeen-and-a-half holes to go,” he said grimly.

By the time he reached us in the fairway, DiMare noticed something was wrong.

“Fish, what the hell is going on?”

Fish pointed to his shoes, and DiMare hardly broke stride.

“What size are you?” DiMare asked.

Fish paused.

“C’mon, man, I’ve got a few pairs of 11-and-a-halfs in the locker room. I’ll run for you right now, what size are you?”

The two continued like this for some time, until it became clear that DiMare would not accept no for an answer. Either Fish had better find some new shoes, or DiMare would find them for him. The exact manner of shoe acquisition has escaped me by now, but I know that Fish walked the rest of the round with us far more comfortably and that DiMare tipped generously. I also know that I never questioned DiMare’s reputation again.

I was sad to learn that Steve DiMare died suddenly — and young — earlier this year, leaving behind a loving family and a visitation line wrapped around the street.

Eventually we are all memories. May we hope ours are as righteous.

***

When people ask me about my experience as a caddie, DiMare’s is the first story I tell. In so many ways, he is the embodiment of life at Long Island’s friendliest country club, the Rockville Links.

But it doesn’t take me long to reach the rest of the stories listed above. They are equally instrumental to the job that birthed a life in golf.

You can watch GOLF.com’s video from Rockville Links set alongside Long Island’s other private golf gems, at the link below.

I would be remiss if I did not also thank the following:

The Links

NICKY and BRIAN are two lifelong buddies, and two longtime loopers. They were the first people who taught me that golf is a creative endeavor first and a sport second. I am indebted.

DONATO was a fellow teenage idiot in the caddie yard, and fellow LICSF recipient. He owned a Dodge Charger, paid for by his caddying funds, by our second summer. He remains the hardest-working person I have ever met.

STEVIE is another grinder, and a great friend. I am grateful to have remained in his orbit.

RICHIE, in charge of the bag room, is a voracious reader and sports media consumer. He never failed to connect me to people around the club with ties to sports media.

JASON SCHUIT was kind to me when I was a caddie who had absolutely no idea what I was doing. He was kind to me again, in much the same way, when I returned to the club last month to report on this story. You don’t forget people like that.

FRANK TROISE taught me you can be the smartest person in the room and also the kindest.

JOHN CULKIN and DON DIBRITA JR. indulged my goal to come back and loop at a place I hadn’t worked in half a decade. They, like so many others listed above, help make The Links special. JEFF CULLINAN gave me one last loop.

You can reach the author at james.colgan@golf.com or @jamescolgan26.