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Home»News»6 Tales from the Bag
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6 Tales from the Bag

News RoomBy News RoomJuly 7, 2025No Comments5 Mins Read
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The Journey of a Caddie: My Experience at Rockville Links Club

The most important job interview of my life lasted less than five minutes. I found myself in the pro shop at the Rockville Links Club, hoping to earn a coveted summer position as a caddie. Jeff Cullinan, the caddiemaster, raised an eyebrow and simply asked, "So, do you like golf?" At the tender age of 18, I was naïve yet eager, and I hoped my passion for the sport would help me secure this opportunity. The Rockville Links, a small Long Island country club renowned for its rich golf culture, offered a caddie program that seemed like the perfect way to spend my summer after freshman year at Syracuse University.

This job interview was unique. Both Jeff and I had something to gain; he could make a member happy by hiring me, while I sought my first job in an environment that fused social interactions with the love of golf. Being a caddie was a gratuity-only job, putting pressure on me to shine in order to earn tips. I had rehearsed my lines, telling Jeff, "I love golf! I’m an 18-handicap." Unbeknownst to me, this answer would expose my inexperience when he followed up with a probing question. "What do you usually shoot?" Caught off guard, I stumbled for words, yet somehow, Jeff still handed me a green caddie bib, and I was set to return the next morning at 6 a.m.

After my first shift, I quickly became part of a unique camaraderie that existed among the caddies and the members. The dynamic life as a caddie involved not just carrying bags but also providing support, advice, and companionship on the course. My first day saw me paired with Kevin, a seasoned caddie known for his militant focus and kind demeanor. Kevin was patient, teaching me invaluable lessons such as the three commandments of caddie life: "Show up. Keep up. Shut up." These simple yet profound rules became cornerstones of my caddie experience at Rockville Links.

As luck would have it, my first real loop was with a member named Jane. I was nervous and eager to impress. In my excitement, I flubbed a simple task, accidentally hitting her with her own driver as I attempted to assist her. To her credit, Jane later laughed it off, but my ego took a beating that day. Despite some initial blunders, I was delighted to immerse myself in this new world. The camaraderie, physical activity, and ever-present opportunity for tips kept me returning to the course each day.

The caddie life opened doors I never imagined. I met an array of fascinating people, including Chris Heckman, a member who offered more than just monetary support; he cultivated my passion for golf. His insights during our rounds were priceless, and before I knew it, the nickname "Uncle Chris" fit him perfectly. Our conversations stirred a love for the sport that grew with every game we played together. In time, he became a significant influencer in my journey toward becoming a golf writer.

Through my time caddying, I learned more than just about golf; I understood that the sport bridged connections. One memorable opportunity arose when I was looped for Jim Tomlin, a friendly face at the club and a member of the Long Island Caddie Scholarship Fund board. We not only built a rapport but also forged a lasting connection. He ultimately sponsored my application for a scholarship that helped alleviate some financial burdens during my college years at Syracuse.

Similarly enlightening experiences came in the form of Steve DiMare, affectionately known as "DiMare" to all. During one memorable day, I witnessed his leadership qualities first-hand when a fellow caddie faced an unfortunate equipment malfunction. With his self-assurance, DiMare arranged for the man to get new shoes mid-round, proving that his kindness extended well beyond club protocols. Learning from such influential figures prepared me for my aspirations in the sports media world.

As the seasons at Rockville Links rolled by, I transitioned from the bottom-most rung of the caddie hierarchy to more regular loops, each encounter offering lessons in professionalism, sportsmanship, and the sheer love of the game. The wealth of stories lived through my four years of caddying still resonates deeply with me. From laughter on the greens to moments of personal reflection, each shift helped network my aspirations, granting me experiences that transcended mere summer employment.

Looking back, I realized each encounter enriched my journey. From the laughter shared with my fellow caddies to the lessons taught by seasoned members, the bonds formed at Rockville Links provided a foundation upon which I built my career. With gratitude, I carry those experiences into every aspect of my life today. Caddying taught me that the heart of golf is not only found in the scores but also in the connections forged through shared laughter, challenges, and triumphs on the course.

In conclusion, the lessons learned at Rockville Links Club have left an indelible mark on my life. My journey from a naive teenager with limited golf knowledge to a passionate advocate for the sport encapsulates the essence of what being a caddie is about. The caddie life taught me about golf, but it also taught me about resilience, community, and the ability to navigate challenges gracefully. My encounter with the complex world of golf lays the foundation for a career still unfolding, reminding me of the friendships and experiences that brought me to this point. As I continue to follow my passion for golf writing, I also carry forth a commitment to share the sport’s beauty and its role as the ultimate connector in our lives.

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