Pickleball, Anyone?

Silly-sounding? Maybe. But our writer gets right on court to find out what it takes to succeed at this sport, who’s playing and why Southwest Florida is a hotbed for it.

BY December 27, 2017


The score is tied, and I’m determined to win. It’s a cool day, but I’ve already worked up a sweat. I wipe my brow and await my partner’s serve. I haven’t won a game today, but victory is so close. Knees bent, weight slightly forward, paddle out in front—I’m focused. Who knew I’d be this intense over a game of pickleball?

Pickleball—it’s a silly-sounding sport. The first I heard of it was nearly a decade ago when I read that pickleball courts were going in near where I lived. Strange to make such an investment in something that could be a fad, I thought. Then, every few years or so I’d hear about a local pickleball league or sign-ups for a pickleball tournament, or I’d head to play tennis and find pickleballers had taken over half the courts.

Little did I know, it’s never really been a fad. The history of the game actually goes back to the ’60s—when a former Washington state congressman played with family friends on an old badminton court—and has been growing ever since. About 2.5 million people play the sport, according to the Sports & Fitness Industry Association. The stereotype is that it’s primarily played by an older crowd. And, yes, players in their middle age on up make up the core demographic. But there’s a growing contingent of younger people who play at school and even a select few who travel the world to play competitively.   

As it so happens, I’ve landed in a pickleball hotbed. Naples is considered one of the premier locales for the sport, with plentiful courts and one of the largest tournaments in the world, the Minto US Open Pickleball Championships. I can’t deny it anymore. Pickleball is here to be taken seriously. It’s about time I explore this new world.

I arrive early one morning at East Naples Community Park. Players are starting to fill the courts before the day heats up. Pickleball courts dot Southwest Florida on private and public properties, but East Naples Community Park is the epicenter of the sport. It has 44 courts and a dome-like structure that casts shade over a portion of them. The US Open Pickleball Championships brought in 800 players here for the inaugural tournament in 2016, then about 1,300 the next year. Competitors came from more than 42 states and 17 countries. Some stayed for days in the area, making it a mini-vacation in April and pumping about $4.5 million into the economy.

Today, the crowds are coming for recreational play. The thunk-plink-thunk of volleying fills the air. It’s like watching Mini Tennis. Or Big Ping-Pong. The paddles are larger than a Ping-Pong paddle but still have a solid face. The balls are larger than ping-pong balls but are lightweight, made of perforated plastic. The action is fast-paced with lots of volleys and quick movement. All of this played in a box roughly half the size of a tennis court.

I’m here to meet Jim Ludwig. Trace the history of pickleball in East Naples and a lot of it leads through the Massachusetts transplant. He was instrumental in turning the dilapidated tennis courts and skate park at East Naples Community Park into the pickleball destination it is now. He helps run the US Open championship and the Southern Tropics Pickleball tournament circuit. He has taught through the Naples-based US Open Pickleball Academy, and he founded with his wife Pickleball for All, a nonprofit that provides equipment to local schools.

Jim arrives and stops to shake a few hands and say hellos to the other players. During my time with him, I’ll find this happens quite often. If you play pickleball in Naples, chances are you know Jim, and when you see him, he’ll ask about your game, your well-being, or just exchange a few pleasantries. He’s the unofficial mayor of Pickleball City.

As he explains, pickleball became his passion project in retirement. Not just playing, but spreading the good word about the game. One of his favorite stories to tell was the time he set up a demonstration at AMIkids Big Cypress, a facility for troubled youth in Ochopee. Through his Pickleball for All nonprofit, he arrived with nets, paddles and balls in tow, along with a few other high-level local players. The kids were on lockdown, but Jim marked off space on the basketball courts and started playing. He could see the kids watching through the windows, and when the lockdown was lifted, one by one, they started to come outside. By the end of the day, two dozen boys were playing. “You should have seen them; they were having so much fun,” he says. He ended up leaving the equipment behind.

Funny thing: For all his involvement now, Jim retired to Naples not knowing anything about the sport. He played racquetball and tennis. Pickleball? Sounded silly. Then he played. “I fell in love instantly,” he says.

I asked about possibly getting a lesson, and he was happy to oblige.

Jim Ludwig playing at East Naples Community Park.


The night before my first lesson, I set out to research the game and stumbled across videos of pickleball pros performing tricks shots—balls hit at angles so they curve around the post of the net and land in-bounds on the other side. Cool stuff like that. Mentally, I start preparing my own list of tricks (a between-the-legs shot looks doable) and ultimately become fully aware that I’m way ahead of myself.

I arrive at the court the next morning realizing that I don’t even know how to serve. The nice thing about pickleball is that it’s not too difficult to learn. The serve is an under-handed stroke (think bowling), where the ball is struck below the waist. The goal is to place it in the box kitty-corner to you. Once you have that figured out, the game comes down to a series of volleys. (You can hit the ball out of the air or take it off a bounce.) If you know tennis, the volley part should come easy. It’s reflexes and reactions. The feel and movement of the ball is different. So it’s a matter of practice. But I’m eager to move on from practice, and after our quick lesson, Jim starts to scare up a game.

Another nice thing about pickleball: It’s a very social game, Jim explains. Games don’t take long, so there’s a lot of rotating. Many people play with partners, but at East Naples, you can show up by yourself and land in a match.

Doubles is the way to go, Jim says. Most people play doubles. Not that there’s anything wrong with singles, but it does require quite a bit more running and pivoting, which can be hard on aging knees. Jim’s friend Mike O’Leary arrives with his wife, Cindy. Mike is an experienced pickleball player, with some deep runs in tournaments. Now, he’s entered a new challenge: learning pickleball in a wheelchair.

We pick up a fourth player looking for action, Anita Waddell. Anita is a regular, as well. She went from novice to serious player quickly. Now, it’s a game her whole family can play. Her son, Noah, in addition to being a world-class piano talent, also medaled in the juniors division at last year’s U.S. Open. She stresses how easy it is to pick up and how accessible it is to anyone, no matter skill level or age. It’s something a 70-year-old can play with a 20-year-old and keep up.

I’m the youngest on the court—but that makes little difference. As we progress, it becomes clear that Mike may have the best reflexes out of all of us, snagging balls out of the air, nimbly rolling to catch them on the bounce (wheelchair players get two bounces). Jim and I have teamed up, and we get routed (my fault). My biggest issue is footwork. The goal is to get up close to the net. A big difference from tennis is that in pickleball there’s a 7-foot alley before the net commonly referred to as “the kitchen.” You can’t be in the kitchen and hit the ball. The trick is staying just outside but still close to the line. My problem is that I keep drifting back a few feet, into no-man’s-land where I have to lunge for balls sailing at my feet.

I whiff a lot, too. I find myself longing for my tennis racket.

After our first game, I sit with Mike and Cindy for a bit.

Mike has been a sportsman all his life. His sport was squash. He picked up on pickleball once moving to Marco Island and got pretty good. He also lives with Lewy body dementia, a condition that affects the brain and body—memory loss, confusion, and what’s essentially a lack of communication between the mind and legs.

The turning point in his pickleball career came during the U.S. Open in 2016. He was progressing in the tournament, but he kept falling. The fourth time he fell, he knocked his head on the court and suffered a concussion.

Now, he has difficultly taking any more than three to four steps at once. But the lifelong athlete didn’t want to put his playing days behind him. He found an athletic wheelchair, which features wheels turned at an angle, and started a new phase of his pickleball career. “I fall asleep thinking about pickleball,” he says. “I wake up thinking about it.”

Jim Ludwig (far left) and Carol Caefer play against Mike and Cindy O'Leary at East Naples Community Park.


I team up with Mike for our next round, and Jim finds a fourth after Anita leaves to play with her usual partner. I find that I’m starting to get the hang of it a bit more. Power comes in handy, of course. But in doubles, it becomes more about placement. Oftentimes, a tap is better than a kill. Mike and I come close in the second game, but the game ends when I whiff on a ball in the corner. “It was great form,” Jim says with a smile. “You just need to hit the ball!” Point taken.

Midway through the third game we get a little nasty. By nasty, I mean some nasty spin. Jim lofts up what looks like a perfect chance for me to put one away, but it dinks off my paddle and into the net. How did that happen? I’m starting to get into a new level of play. I get tricked by spin a few times, the ball angling just enough off a bounce to throw my swing out of whack. But I’m catching on and, along with Mike getting a little nasty on his shots, we’re close as we reach game point. (Games go by a single point to 11, but you’re only able to score when your side serves.) This is when my competitive side kicks in. I get in position. I focus. And, I whiff. I whiff on a ball at eye level. Tragic. (I blame the wind.) The serve goes over to their side. They score again, and then after a good volley, Jim angles one by Mike and we go down 10-12.

Like all of our matches, we gather at the end to tap the ends of our paddles. It’s like shaking hands and saying “good game.” It did feel like a good game, too. As I leave the courts, I’m still lamenting my whiffs, but I’m refreshed from the good workout and thankful pickleball didn’t turn out to be a fad after all.

The next day I talk to Kyle Yates. I’d been meaning to track down Kyle because the Fort Myers native is the next wave of pickleball talent in the world, an example of what the sport is becoming.

Kyle grew up playing racket sports. He played tennis at Cypress Lake High School. He was good—but not big-time college good. He had an uncle who introduced him to pickleball. It was a perfect fit—the right combination between tennis and Ping-Pong that he was both immediately good at and had a blast playing. He went to the University of Florida but spent his weekends traveling to The Villages, which had a thriving pickleball scene. Just three years after picking up a paddle, he was traveling to play competitively.

Now, pickleball is his profession. He teaches with the US Open Academy in Naples and travels worldwide to compete. He’s been across Europe, traveled coast-to-coast in the states. He’s won back-to-back doubles titles at the US Open. Winnings may be only a few thousand per tournament—$3,000 was the highest he’s won. But he also has sponsorships, such as one with Paddletek, which help with expenses, and in turn he helps market their wares.

Kyle was in one of those videos I watched at first. It changed my perception of the game. This wasn’t just tapping a ball over a net. In part, what draws Kyle to the sport is that ability to push things forward. He’s a pioneer of sorts in a game where the end point isn’t quite clear yet. It’s hard for anyone these days to say they created a new tennis shot or achieved something that no one has done on a tennis court. Kyle can say that with pickleball. “We’re keep pushing in a new direction,” he says. “You watch some of these (former) tennis players doing things we’ve never seen in the seen done before. It’s exciting. You see it and say, ‘Wow, this is intense. This could be an Olympic sport.’”

The future is what’s exciting. And so much of that future is here in Southwest Florida. On the Punta Gorda campus of Florida SouthWestern State College, construction is underway for the PicklePlex. It’s a large facility with indoor and outdoor courts, a pro shop, a fitness center, and even a restaurant and bar. Down in Naples, ambitious plans are also underway at East Naples Community Park. Ten more courts and a new pro shop are on the way. Jim imagines a sports bar-like restaurant with rooftop seating that overlooks the courts. Cameras on each court so you can tune in and watch while you eat. “We can make this a world-class destination,” he says.

Yes, it’s a silly-sounding game. But its future here is serious business. I’m not sure where I’ll fit in to that future. Even if I don’t pick up a paddle again in years, I’m confident this time I’ll be able to find a good match anywhere.


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