John Jaso knew he wanted to retire, so he started shopping for sailboats. It was the 2017 season and Jaso, the first baseman for the Pittsburgh Pirates, was spending his free time at home browsing boating websites. And when the Pirates visited a team near a body of water, he would wander the marinas and imagine he was on the open water.
One June morning in Baltimore, before a 7:10 PM first pitch against the Orioles, Jaso rented a car and drove to Annapolis, Maryland. There he found the boat he was looking for: a 2014 Jeanneau 44 DS. He had it examined, bought it and had it shipped to his off-season home in St. Petersburg, Florida. He got back to the stadium in time to go 2 for 4 with an RBI
Four months later, when the Pirates’ season ended without a playoff spot, a handful of reporters came to Jaso’s locker and asked him what his plans were. He had reached the end of his two-year, $8 million contract with the team and was set to become a free agent. He told them his next destination would be somewhere in the Caribbean. He was retiring.
‘I have a sailboat’ he said“So I just want to sail away.”
Five years later, as pitchers and catchers streamed into spring training camps in Arizona and Florida on Monday, Jaso, the last catcher to catch a perfect game, has no regrets about sailing off into the sunset. “Sometimes I’m just sitting on the boat, floating in the water, not sailing or even fishing, and I think to myself, ‘There’s no other place on the planet I’d rather be than here,’” he said. “It was a perfect fit for who I am.”
Jaso’s baseball journey never went so well. Tampa Bay selected him in the 12th round of the 2003 draft, and by the end of the 2008 season he had reached the majors. In his nine-year career he was traded three times, and then he switched from catcher to first base sustain multiple concussions. But he had plenty of highlights, too: He caught Félix Hernández’s perfect game in 2012 for the Seattle Mariners — there hasn’t been one since in the MLB — and hit for the first cycle in PNC Park history when he was with Pittsburgh in 2016. Its long Dreadlocks towards the end of his career made him almost instantly recognizable. And he earned more than $17 million in career earnings, according to Spotrac.
But he found MLB life unfulfilling in some unexpected ways. “Baseball set me up for life,” he said. “I love it and I respect it. But it was part of this culture of consumerism and overconsumption that really started to weigh on me. Even when I retired, people were saying, ‘You might be missing out on millions of dollars!’ But I had already made millions of dollars. Why do we always have to have more, more, more?”
Sailing filled the void in his life. He familiarized himself with every foot of the ship. He took a diesel engine mechanics course and installed solar panels and a wind generator. He devoured hours of YouTube videos about the electronics, making sure he knew what each wire did. “If something goes wrong in the open ocean,” he said, “I’m the only one who can fix it.”
The only thing left: learning to sail.
He found an ad for a sunset cruise on Craigslist and emailed the captain, offering a few hundred dollars for a crash course in boat handling. After a few hours, he felt comfortable enough to go it alone. “It was like learning how to hit a fastball and lay off a slider,” he said. “You hear coaches talk about it all day long, but you never really learn it until you’re actually in a game.”
Jaso named his boat Roaming Rose and started taking day trips to the Gulf of Mexico in early 2018. One day that spring, while working on his boat, he was struck by a sudden and strange sensation. “I thought, something feels really strange right now,” he said. “Like I forgot something. And then it dawned on me: I should have been in spring training. I started laughing because I realized: I didn’t miss it at all.”
A few weeks later, he made his first major voyage. He sailed south to Key West and stayed on the boat for three weeks before heading to the Abaco Islands in the northern Bahamas, where he spent most of a month anchored in a sheltered bay. He left when he heard about a major storm moving across the Atlantic. He avoided most of the wind and rain on the five-day sail home, but on the last night, he said, he encountered heavy winds and lightning.
On deck, he kept one hand on the wheel and one hand on his go-bag. His life preserver was securely tied in case he was thrown overboard. He saw lightning strike the sky and feel the waves shaking the boat. He alerted the Coast Guard to his position and called his brother as backup. After a few hours of fighting he was back on dry land.
“At that moment you’re terrified and you want to get as far away from danger as possible,” he said. “But once it’s over, you appreciate where you are more. There’s a euphoria that comes over you when the storm clouds part. It’s like holding your breath underwater and then coming back up to the surface and taking that first breath of air.”
When Jaso described the experience to Fernando Perez, a friend and former teammate, Perez wasn’t the least bit surprised. “Playing professional baseball is like a drug,” said Perez, now a video analyst for the San Francisco Giants. “When you retire, you have to find another high. The drug John found was being in the middle of nowhere and keeping himself alive. That first storm didn’t scare him. He enjoyed getting caught up in it.”
The first two years after his retirement, Jaso spent about six months of the year on his boat. For the rest he was based in St. Petersburg. Although he said he no longer follows baseball, he tries to play one or two games every year. In 2018, during a Rays win over the Boston Red Sox, he tried to go to the dugout to say hello to some former teammates. But an usher noticed his tie-dyed, sleeveless T-shirt and the lack of a tag and waved him back to the cheap seats. Finally, another messenger recognized him and abandoned him.
He also made several trips to Europe, during which he discovered a passion for exploring his father’s ancestral lands in the Basque Country in northern Spain. And he has driven around Australia and Indonesia in a camper. But the boat is his greatest pleasure. “I want my life to be simple, and it doesn’t get any simpler than being on a sailboat,” he said. “You treat the boat right, and she treats you right. That’s all.”
Before the pandemic, he docked Roaming Rose in Turks and Caicos. Due to travel restrictions, it was stuck there for almost two years. When he was cleared to come back and pick up the boat in 2022, he took his girlfriend Jayden Davila on a three-month sailing trip around the Caribbean. They docked in the Dominican Republic, Puerto Rico, the US Virgin Islands and the British Virgin Islands.
“John is generally a pretty peaceful person,” Davila said. “But there’s a different level of peace and happiness for him when he’s on the boat. Even when there’s trouble — and there’s always something going on — he’s enjoyed dealing with it. When things are calm, sometimes he’ll just pick up his guitar and start playing. It’s a really beautiful existence for him out there.”
Jaso still lives mainly in St. Petersburg, where he manages some investment properties. But he rarely stays in one place for long. This winter he went snowboarding in Colorado and Wyoming. He will be back on the boat again in the spring.
“When you sail, you go back to something primitive,” he said. “You remove yourself from the material world — this concrete, electronic world. And you go back to this sense of wonder. It’s the same feeling you get when you hold a newborn baby, look into their eyes, and feel the world around you disappear.
“Sometimes it’s easy to forget that we all come from the same place. When you’re on the water, you remember.”
