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You are here: Home / Archives for Gary Cardillo

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

The Angels Who Walk Among Us

April 3, 2026 by Gary Cardillo

I think the first time I was old enough to understand the concept of an angel was when I looked at a nativity scene depicted on a Christmas card where two-winged figures were looking over the shoulders of Jesus Christ’s parents at their child in a manger. I didn’t know if this was strictly a Catholic thing, as none of my Jewish friends ever mentioned anything about having an angel of their own. I naturally assumed that to be an angel, you had to wear a white gown of sorts and wings any bird would envy. As I got a bit older and started losing my baby teeth, I was introduced to a nighttime visitor known as the Fairy Godmother. Sometime during my sleep, she would recycle my teeth and leave me with a quarter under my pillow. At that time, I wish I had more teeth to redeem, as a quarter was a lot of money for a child back then. I found out she, too, had wings, which was confusing, as she had wings, but was called a fairy instead of an angel. They both seemed nice, so the only common denominator I could figure out was that there had to be something in the wings, since neither appeared to be able to fly. Years later, I learned it was better to be considered an angel than a fairy, but I still associated angels with wings, which disqualified me.

For the longest time, I couldn’t figure out what the qualifications were for being an angel, as I never met one, and most of my friends and I made too many mistakes along the way to be remotely considered for “angelhood.” However, things changed the first time I heard my mother refer to someone as an angel. Imagine the look on my face when I saw my first one in real life, and no wings! Guess like Jesus, who wasn’t recognized as anything special by those in his hometown, there didn’t seem to be anything particularly special about the lady my mother was referring to. It was then that I started to understand what it meant to be an angel.

Given what makes someone an angel in the eyes of others, I think the first one I met was my mom. She was kind, patient, encouraging, and saw the best in others. I never heard her say an unkind word about anyone. While you may know others who embody the same qualities, it was her act of honesty that left an indelible impression on me. Years ago, when I was in my pre-teen years, our church was having a raffle, and the grand prize was a new Volvo automobile. A very prestigious prize back then. A dear friend of my mother’s had left to visit family in California and couldn’t purchase a ticket before she left. She asked if my mother would purchase one for her, along with one my mother purchased for herself. As luck would have it, one of the two tickets my mother purchased was the winning ticket, and when everyone congratulated my mother, she replied, “That was the ticket I bought for Dorothy.” As you can imagine, those who approached my mother said, “Dorothy would never know,” but my mom replied, “I would.” There would be many other examples I learned from her over the years, but her act of kindness and honesty was a hallmark moment for me, not to mention a tremendous life lesson.

Recently, our church here in Punta Gorda lost its Pastor who passed away in his sleep. His name was Father Jerome Kaywell, or Father Jerry as he was known to us. A Grammy Award recipient, composer, songwriter, and cancer survivor, who was one of the kindest souls you could meet. I had an opportunity years ago to interview Father Jerry for one of our monthly newsletters and felt the presence of someone uniquely special. He often used the term “mysticism” as part of his spiritual belief, which transcended the personality traits we have grown accustomed. He thought on a higher level. He wanted the church to think and embrace a higher level of thinking and understanding, where we would be more accepting of others, particularly those who didn’t necessarily share our core values. At 72 years of age, he was taken too early from us, but he impacted so many lives. He often confided in close associates his desire to be acknowledged as a Saint, which to me takes Angelhood to a whole new level. I don’t think you can find anyone who doesn’t feel they are a better person for knowing Father Jerry, and I count myself as one.

As I’ve gotten older, I’ve realized that those we consider “angels” don’t fit a physical mold. Many times, it’s not their spoken word, but a certain presence that inspires us to be better. It can be through the gifts they share or just an act of kindness that gives us a paradigm shift in how we view the world, fostering a desire to make a difference in the lives of others.

Recently, I attended an awards ceremony hosted by some of the area’s Rotary Clubs held at the Charlotte County Events Center. Several hundred people were in attendance to acknowledge the acts of heroism, service, and support our firefighters, law enforcement personnel, and unique individuals provide to our community on a continuous basis. While each story was touching, with many risking their lives to save others, it was the look of gratitude on the faces of the lives they touched that you sensed would go on to perform the same acts for generations to come.

Of those who were recognized on that special evening, former educator, school community liaison, friend to many, and founder of the rock-and-soul band called the Boogiemen was Mike Riley. In his various capacities over the years, he has touched the lives of scores of people. His band was one of the most sought-after bands in all of southwest Florida, performing at over 180 charitable events over the decades. Riley, as he is known to his friends, has had a passion for the area’s children, encouraging them to pursue the goals and dreams they embody. Always self-deprecating, Riley has always celebrated the gifts and successes of others, and in his acceptance speech for the Charlie Shue Award, he encouraged those in attendance to make our community a better place for the children and to lead by example. It wasn’t the award he received, but an opportunity he would have, while battling a debilitating health issue, to inspire us all.

This award ceremony would leave us one last defining moment, when recipients of the Punta Gorda Police Department’s program, “Do the Right Thing,” were acknowledged. While we think of those unique individuals who impart years of wisdom from lives well lived, it was a young elementary school girl, whose intervention in saving the life of a fellow classmate contemplating suicide by jumping down a stairwell, made all of us realize angels are all around us. With poise and understanding, she coaxed her classmate to safety, with maturity and composure that far exceeded her years.

These are just some of the angels who walk among us each day. Their words may be simple. Their acts of encouragement, when needed most. Other times, it may be a warm embrace or a listening ear. But they all seem to have the same effect in leaving you with a better version of yourself and a desire to touch the lives of others.

This Easter season is a reminder for many of the life one person gave for so many others. It is with that same service to others that will inspire us all to make this world a better place for generations to come.

-Gary Cardillo

 

Filed Under: Community Information Tagged With: 2026, angels, easter, flwaterfront, jerome kaywell, mike riley, newsletter, real estate

2026 January/February Newsletter

April 3, 2026 by Gary Cardillo

Filed Under: Buying Real Estate

A Different Kind of Gift

April 3, 2026 by Gary Cardillo

Filed Under: Buying Real Estate

A Season That Reminds Us What Truly Matters

April 3, 2026 by Gary Cardillo

Filed Under: Buying Real Estate

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