Like a hurricane, pickleball is sweeping across the nation. So much so, supply is trying to catch up with demand. Everybody I talk to is playing, and one group in Pensacola is seizing the opportunity to capitalize on the pickleball craze in impressive style. Get ready for Portside Pickle.

I met with Wilbur Matthews, “Head Pickler in Charge,” and Aly Watts, “Director of Energy,” at the new pickleball complex under construction at the Port of Pensacola. When it’s all said and done, Portside Pickle will be one of the largest pickleball facilities in the Southeast, and without a doubt, one of the coolest facilities on the Gulf Coast. 

I was introduced to Wilbur through Scott Remington, one of the three partners, along with Rob Fabbro. Wilbur and Scott are best friends and were roommates at Sewanee: The University Of The South. Wilbur’s family, from San Antonio, will soon join him in Pensacola this month, just as Portside Pickle opens.

There are many popular racket sports, but none more popular than Pickleball in America. First created in 1965 out of a garage in Bainbridge Island, Washington, to keep children entertained during the long summer break, Wilbur tells me there is now a line at every city’s mayor’s office asking for more pickleball courts to be built. The numbers are staggering.

I was intrigued to learn more about the sport, and who better than Wilbur, a passionate pickleballer whose temporary office near the Portside Pickle construction site has a framed ATTAWAYTOGO certificate from Camp Longhorn in Burnett, Texas, naming him as ‘1983 Best Pickleball Player, Third Term.’

“I got hooked,” he says. He and his wife play three times a week with friends. When Scott told him about “this opportunity” in Pensacola, he quickly jumped on board. What is it about pickleball, I ask? “It’s a highly social game, with an abundance of opportunities to play for free all over the country. The barrier to  entry from an experience and cost perspective is minimal.” You can basically play for free, he says. “Pickleball is almost always a doubles game, and has an 8-times higher utilization rate than tennis.” 

I immediately picked up that Wilbur is a numbers guy. Having spent most of his career in the financial world as a bond trader and financier with J.P. Morgan and with AIG as a corporate research analyst, he opened his own shop in San Antonio, Vaquero Global Investments.

Two years ago, the property where Portside Pickle is located was once a large, vacant warehouse originally built to store bulk materials being transferred in and out of the Port of Pensacola. I had actually been in that warehouse many moons ago, sampling some cargo that had just arrived. I remember it because it has the largest floor space in Pensacola, larger than the Bay Center. It’s a wide open space, and perfect for indoor pickleball courts. 

Before Scott and Wilbur teamed up and began looking to secure a lease from the City of Pensacola, the underutilized building hadn’t had a long-term lease since 1979, and housed three Mardi Gras floats for $40 per month each. 

Now, with almost 3 acres for indoor and outdoor courts with spectacular views of the harbor and Pensacola Bay, Portside Pickle’s next-door neighbor is American Magic. The potential to establish a sports and entertainment mecca in the heart of downtown Pensacola was too good to pass up.

“We plan to be a destination venue out of the box. We have 240 free parking spaces adjacent to our site, the Pensacola Bay Ferry next door, and we are  400 steps from Palafox and Main. Free parking in downtown Pensacola is rare these days. There are only 18 dedicated pickleball courts in the area, and four additional courts have just opened in Gulf Breeze. There are not nearly enough dedicated quality courts within 50 miles,” says Wilbur. 

He goes on, “There is a huge pent-up demand. The closest dedicated pickleball complex is in Daphne, and a new complex just opened in Foley. Most courts available today are multi-use gymnasiums or repurposed outdoor tennis courts, many with no restrooms. When complete, we will have the largest modern, high-quality pickleball complex within 200 miles, and the potential is incredible.”

“Pensacola is a difficult place to play pickleball. It’s essentially a pickleball desert. Industry recommendations would call for double or triple the number of courts available today to meet demand. With the growth in the sport, Pensacola needed to address the demand.”

When Portside Pickle opens for play later this month with 3 outdoor courts and 5 more scheduled to open this summer, it will signify a two-year effort to attract locals and travelers to Pensacola to play pickleball and socialize. The complex will have a bar and room for two food trucks, with a beautiful outdoor space for dining and visiting with friends when not on the courts.

Aly Watts met Wilbur through a mutual friend. She was “born a Buckeye” in Columbus, Ohio, and her mom introduced her to pickleball at a young age. After graduating from Ohio State’s Fisher School of Business with a degree in Business Economics in 2019, she worked for Vanguard Investment Advisors. Aly met her boyfriend, Matt, who graduated from the University of Alabama with a degree in Management Information Systems, and is from Gulf Breeze. 

A friend of Matt’s family in Pensacola was doing a year-long yachting “Great Loop” (another story for another day) north via rivers through the U.S. and Canada, and needed a house-sitter for the summer. “I kept telling Matt, I love it here, but there is no pickleball. Where can I play? There weren’t many options, and I was desperate to play.”

Serendipitously, Aly met Wilbur, and he invited her for an interview. After four hours and multiple follow-up interviews with the three partners, Wilbur asked Aly to create a job description and title. “Make it fun,” he told her. She thought, “These guys are on to something and gave me so much freedom to be creative. Two and a half weeks later, I told them I wanted to be Director of Energy and was hired on the spot.”

Aly tells me the goal is not just to add courts, but to build a community. “Pickleball is a sport played by everyone regardless of age, race, or background. It’s a social game, and you play with everybody. You meet people, you make friends, and there is a low barrier to entry. Players are happy to show newcomers how the game is played, and it’s super-fun and easy to learn.” 

“Pickleball becomes a home away from home. It’s a place to go after work, get outside, meet new people, and foster relationships away from our phones. You figure out pretty quickly what to expect, who to expect, and have some fun. Pickleball players come from all walks of life and are a high-quality demographic.”

That becomes more evident as Wilbur excuses himself to meet with a potential sponsor. “We are amazed at how many companies want to be affiliated with pickleball. We get multiple calls per day. They see the potential of teaming up. The fundamental is that people want to play. The sport is so nascent, and just now beginning to display signs of future potential.

It’s estimated that the paddle market is a $2 to $3 billion market. Since pickleball grew up in garages, there are over a thousand paddle manufacturers. Marketers are coming out of the woodwork to affiliate with the sport. The two organizations that track growth in pickleball estimate there are between 14 million and 47 million players in the U.S. I suppose the real number is somewhere in the middle.

“Younger people are rushing into the sport,” says Wilbur. “It’s the fastest-growing sport in the last 5 years. There are 10 universities with over 1000 pickleball club members, far exceeding any other sport. Auburn has a huge club membership. Opelika, Alabama, near Auburn, is the largest pickleball complex near Pensacola. People are driving long distances to play tournaments.” 

He continues, “Tennis is hard, pickleball is easy, and the cardio is better. There’s something magical about it. You’re standing 14’ apart, games last about 15 minutes, and then there’s a break where it’s highly social. It’s a game that anyone can play and share a common interest. You’re creating a community.”

We talk about the impact of Portside Pickle. “The challenge is to align skill sets for players. There’s a good formula for that, so everyone is having fun. Then we need to align with the brands that match our vibe. We will have leagues, host tournaments, and offer lessons by certified pickleball coaches. We’ve already held one clinic for coaches, and will have more.”

Portside will soon offer Founder memberships and Single memberships. Each court can serve between 50 and 75 members. They will offer “drop-in” play for travelers and “open” play for members, so there’s always a game available. With the indoor courts expected to be completed by the end of the year, weather is not an issue.

As far as the entertainment factor, Wilbur and Aly hope Portside Pickle will attract non-players who just want to enjoy the outdoors with friends, take in the beautiful setting on the water, and have all the modern conveniences of food, drink, and restrooms at their disposal. With its premier location, Portside Pickle could host other competitions, like cheerleading, or become a music venue for concerts. 

I was excited listening to Wilbur and Aly. Their enthusiasm is infectious. They have a full-scale marketing effort that is impressive and professional. “Pickleball players are ‘joiners’,” says Wilbur. And then he told me what a ‘tweener’ was. “It’s when you run backwards to get to a ball and hit it between your legs for the return.”

I'd better do some stretching.