Sarasota native stops in Rutland on tour to break pickleball world record

By Katy Savage

Pickleball enthusiast Dean Matt made a stop in Rutland on May 21 as he attempts to break a pickleball world record. 

Matt, who calls himself The Pickleball Pilot, is playing pickleball in 48 states in 48 days to become the fastest person to play a game of pickleball in all 48 contiguous states, per the Guiness Book of World Records.

“It has flown by,” Matt said after finishing his game in Vermont. “My wife said it would fly by and it has.”

Matt, who’s been a pilot since high school, is flying his Turbo Cessna 206H six passenger aircraft. He plays two or three games of pickleball a day, each game in a different state.

Vermont was his 36th stop. He played at 10 a.m. at Rutland Racquet Club and then flew a half hour to play another game in Concord, New Hampshire. 

Chris Karr, owner of the Pickle Barrel Nightclub in Killington, picked him up from the Rutland Regional Airport in the Pickle Barrel bus.

“A good time was had by all,” said Steve White, a local pickleball addict (self-described) in Rutland and leader of the Better Friendships Pickleball Tournament. “I’m a pickleball nutcase. I love it. I guess I’m making it so everybody knows that.” 

Matt took on two locals in Rutland and ultimately lost.

“It’s not really about the score,” Matt said. “That sport is exploding. You can grow with it.” 

Matt, 63, a Sarasota, Florida native recently retired as CFO of a company in the cannabis industry and was looking for an excuse to travel around the country.     

“I’m getting older, I just want to go around the county,” he said. “It’s a way to combine my love of aviation with playing pickleball.”

Back home, Matt, a former golfer, plays pickleball three or four times a week. He said pickleball is an easier sport to pick up.

“It’s just easy to play — you just kind of show up at the court and play,” Matt said. 

He said he just had the idea to break a world record. Then “I called some sponsors and they were interested,” he said.  

Matt then called Guinness, thinking the record attempt would garner more publicity. 

“[Guinness] told me ‘no’ about three times,” Matt said.

But Guinness finally agreed and came up with a new category.

 Matt started his record attempt on Monday, May 1. 

He departed the Sarasota-Bradenton International Airport to play pickleball in Alabama before slowly making his way out west. His journey is expected to end Friday, May 26 when he’ll play at University Park in Tampa, Florida.  

The total trip will be around 9,000 miles, with 80 hours of flight time. 

“We’re just having a lot of fun,” Matt said. 

So far, Matt has played with mayors, athletes, including NFL offensive tackle Jordan Mills, as well as ex NBA players, special olympics kids, low income youth and former New Hampshire Gov. John Lynch. 

“I’ll probably come home with a losing record,” Matt said, again emphasizing that it’s about the love of the game, having fun and touring.

To follow Matt’s tour visit: mucho-dean-aero.com/the-pickleball-challenge.