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You are here: Home / Archives for flwaterfrontliving

Rarified Air

October 9, 2026 by Gary Cardillo

Bob DeStefano is a name you may not recognize, but at one time, he was the longest-tenured golf professional in the country and was recognized by the PGA for developing one of the nation’s top junior golf programs. For over fifty years, Bob helped develop a multitude of golfers who competed at championship levels, many of whom became multiple-time club champions, though I was not one of them!

Being one of “Bob’s Juniors,” as we were known, I learned the game of golf at a very young age. However, when you are eight or nine years of age, patience isn’t always a virtue, and as I waited for the foursome of elderly men taking their time to play in front of me as if no one else was on the course, and watching my summer pass before my eyes, I decided teaching waterskiing wasn’t a bad second option.

While I didn’t give up golf, I wasn’t as dedicated to it as some of my other friends who went on to become pretty good golfers. Compared to me, they hit the ball straight and seemed to have all the shots in their bag. As for me, I had a slice second to none, and oftentimes felt I needed to duck after hitting my tee shot, expecting the ball to come back around like a boomerang. That being said, after watching Rory McIlroy at this year’s Masters, playing his errant tee shots from the woods, I felt as if we were kindred spirits. While our local course, St. Andrews South, doesn’t have many trees to navigate, using Rory’s same technique, there are very few houses I haven’t hit!

For those of Bob’s Juniors who took the game more seriously than I did, there are a couple of golfers that stand out, Rick Southwick and Jay Card III, known as “Jake.” Rick was one of the finest golfers I knew early on. I remember seeing him compete in his first club championship at Gardiner’s Bay Country Club on Shelter Island, NY, a club we all belonged to. He was playing against a multiple-time club champion, who was trying to throw Rick off his game mentally, as he appeared to sense he was overmatched. As impressive as this reining club champion was, Rick seemed to be at another level, as he made each shot look effortless. After going on to win multiple club championships himself and beating Phil Mickelson in the U.S. Amateurs, Rick decided to pursue the pro golf tour. Too often, when we see someone we personally know dominate local competition, which can be fierce, we think that it can easily translate to the next level and above. Rick would find that playing to support yourself, and the pressure of competing with so many others with the same ambitions and skill sets, became very sobering, especially when everything you had done before to win club championships was no longer good enough. People who knew Rick from the club and were accustomed to his dominating performances started asking Bob, “What’s the matter with Rick? Why isn’t he winning?” Bob would simply reply, “Rick is performing within the top 5% of everyone in the world who plays golf. If you performed within the top 5% of your profession, you would be considered a success, but you question what is wrong with Rick.” As good as Rick was then, even though his profession has changed, he recently competed in the 65th Senior Amateur Championship, which draws golfers from all over the country. To see his game, you wouldn’t think he has missed a step, as he still plays the game with that effortless confidence.

As talented as Rick Southwick has been over the years, Jay Card III is a name you may be hearing about very soon. Our family has been friends with the Card family of Shelter Island for four generations, and Jay Card III, known as Jake to his friends and family, is currently playing on the PGA Tour’s Korn Ferry Tour. Multi-talented, like his father, who was a decorated athlete, Jake just missed making the PGA Tour a little over a year ago and is competing again with the goal of competing alongside the likes of Rory McIlroy and Scottie Scheffler. Recently, we watched Jake play in the Lecom Suncoast Classic, a Korn Ferry Tour stop held at Lakewood National Golf Club in Lakewood Ranch. A total of 156 professional golfers entered this tournament, and to see the quality of golf up close and personal was a memory of a lifetime. The course was challenging, with stiff winds and unforgiving greens, and the competition was so fierce that even from the vantage point of a spectator, you could feel the pressure knowing one errant shot could take the golfer you were rooting for out of the prize money. It’s hard to believe that after 72 holes of intense competition, Jake would come up just a little over an inch short on his birdie putt on the last hole to miss being tied for first and going into a sudden-death playoff. He had to settle for a two-way tie for second place at 21 under par. A non-golfer may ask, “Is that good?” For someone like me, I would have more success hitting a house than shooting a sub-par round of golf, but to think that last putt Jake missed cost him around $100,000.00 had he gone on to win in a playoff is the pressure these golfers face as they stand over each and every putt.

Unlike team sports, where one player may be able to offset a poor performance by another team member, golf can be a very lonely walk, as you are not only competing against everything the course throws at you, but the hot hand that any given player may be having that day. Simply put, it is when good isn’t always good enough.

What makes Jake’s journey so interesting is that he didn’t come from a big city or attend an elite sports academy like IMG that would have honed his skills and fostered a competitive spirit. He grew up on an island of approximately 2,500-3,000 year-round residents and was part of a graduating class of only 16, including himself. He attended High Point University in High Point, North Carolina, where his original plan was to enroll in a pre-med program, but soon realized it wasn’t the path he wanted to pursue. It is said that his passion for music and his bass voice caught the attention of his professors, who heard him sing with the choir and suggested he pursue a degree in music. While today’s generation’s music interests are about as far removed from opera as I am from being an astronaut, Jake chose a path less traveled, studying opera and graduating with a degree in music performance. This talented young man has sung at Carnegie Hall, as part of an a cappella group, and as a member of university choir, performed at the Vatican. He’s even performed solo with an orchestra in front of 1,500 people.

Whether it is performing solo on the big stage in front of scores of people or competing at the highest level in a sport such as golf, it takes a special individual who is not only willing to make the sacrifice to hone their skills but is also willing to take the road less traveled. Henry David Thoreau once said, “Go confidently in the direction of your dreams! Live the life you’ve imagined.” His quote affirmed the power of self-belief and the importance of pursuing one’s passions. Sometimes that journey can be lonely. As golf legend Arnold Palmer once said, “Golf is a game of inches; the most important are the six inches between your ears.”

We often idolize others’ success, not fully appreciating the sacrifices they made to reach the pinnacle. American comedian, vaudeville performer, and radio/film star from the 50’s and 60’s, Eddie Cantor summed it up best, “It takes twenty years to make an overnight success,” …implying the real work happens years before the spotlight hits.

As Jake walks down that fairway, thinking to himself about the pressure shot he just made, or the one that is to follow, he has already accomplished something most of us were afraid to do. He was willing to take the chance to succeed that few others could say they did.

 

-Gary Cardillo

Filed Under: Community Information Tagged With: florida real estate, flwaterfrontliving, gary cardillo, golf, Jay Card III, newsletter, Rick Southwick

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