John Jaso knew he wanted to retire, so he started shopping for sailboats. It was the 2017 season, and Jaso, the Pittsburgh Pirates’ first baseman, would spend his downtime at home browsing on boat websites. And when the Pirates visited a team near a body of water, he would wander the marinas and imagine himself 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, Md. There, he found the boat he’d been looking for: a 2014 Jeanneau 44 DS. He had it surveyed, bought it and had it shipped to his off-season home in St. Petersburg, Fla. He made it 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 berth, a handful of reporters wandered over to Jaso’s locker and asked him what his plans were. He had reached the end of his two-year, $8 million deal with the team and was set to become a free agent. He told them that his next destination would be somewhere in the Caribbean. Hey was retiring.
“I have a sailboat,” he said, “so I just want to sail away.”
Five years later, as pitchers and catchers began flooding into spring training camps in Arizona and Florida on Monday, Jaso, the last catcher to have caught a perfect game, has no regrets about having sailed off into the sunset. “Sometimes I’ll just be out on the boat bobbing in the water, not sailing or even fishing, and I’ll think to myself: ‘There’s nowhere else on the planet I’d rather be than right here,'” he said . “It’s been the perfect fit for who I am.”
Jaso’s baseball journey was never quite as good a fit. Tampa Bay selected him in the 12th round of the 2003 draft, and he made it to the majors near the end of the 2008 season. In his nine-year career, he was traded three times and switched to first base from catcher after sustaining multiple concussions. But he had plenty of highlights too: He caught Félix Hernández’s 2012 perfect game for the Seattle Mariners — there hasn’t been one in MLB since — and hit for the first cycle in PNC Park history when he was with Pittsburgh in 2016. His long dreadlocks toward the end of his career made him almost instantly recognizable. And he pulled in career earnings of more than $17 million, according to Spotrac.
But he found the MLB life to be 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 began to weigh really heavily on me. Even when I retired, people said: ‘You might be walking away from millions of dollars!’ But I’d already made millions of dollars. Why do we always have to have more, more, more?”
Boating filled the void in his life. He familiarized himself with every foot of the ship. He took a class for diesel motor mechanics and installed solar panels and a wind generator. He devoured hours of YouTube videos about the electronics and made sure he knew what every wire did. “If anything goes wrong in the open ocean,” he said, “I’m the only one out there to fix it.”
All that was left to do: Learn how to sail.
He found an ad for a sunset tour on Craigslist and emailed the captain, offering a few hundred bucks for a crash course in commanding a boat. After a few hours, he felt comfortable enough to go it alone. “It was like learning to hit a fastball and lay off a slider,” he said. “You can hear coaches talk about it all day, but you’ll only learn how to do it if you face it in a game.”
Jaso named his boat Roaming Rose and started taking day trips into the Gulf of Mexico in early 2018. One day that spring, he was working on his boat when he was struck with a sudden and strange sensation. “I thought something felt really weird right now,” he said. “Like I was forgetting something. And then it hit me: I should have been in spring training. I started laughing because I realized: I didn’t miss it at all.”
He took his first big voyage a few weeks later. He sailed south to Key West and stayed on the boat for three weeks before departing for the Abaco Islands in the northern Bahamas, anchoring down in a protected bay for the better part of a month. He took off when he heard about a major storm making its way across the Atlantic. He avoided most of the winds and rain on the five-day sail home, but on the final night, he said he encountered violent winds and lightning.
On the deck, he kept one hand on the wheel and one on his go bag. His life preserver was strapped on tight in case he was thrown overboard. He watched the lightning marble the sky and felt its surges shake the boat. He alerted the Coast Guard to his position and called his brother as a backup. After a few hours of white-knuckling, he was back on dry land.
“In the moment, you’re terrified, and you want to be as far away from danger as possible,” he said. “But once it’s over, you appreciate where you’re at more. There’s this 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 gulp of air.”
When Jaso described the experience to Fernando Perez, a friend and former teammate, Perez wasn’t surprised in the slightest. “Playing professional baseball is a kind of drug,” said Perez, who is now a video analyst with the San Francisco Giants. “When you retire, you have to find another high. The drug that John found was being in the middle of nowhere and keeping himself alive. That first storm didn’t scare him away. He liked getting caught in it.”
For the first two years after 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 does not follow baseball anymore, he does try to catch a game or two every year. In 2018, during a Rays win over the Boston Red Sox, he tried to go down to the dugout to say hello to some former teammates. But an usher saw his tie-dyed, sleeveless T-shirt and his lack of a ticket and waved him back up to the cheap seats. Eventually, another usher recognized him and let him down.
He has also taken several trips to Europe, discovering a passion for exploring his father’s ancestral land in the Basque Country of northern Spain. And he has driven a camper van around Australia and Indonesia. But the boat has been his greatest pleasure. “I want my life to be simple, and it doesn’t get simpler than being on a sailboat,” he said. “You treat the boat right, and she treats you right. That’s all there is to it.”
Before the pandemic, he docked Roaming Rose in Turks and Caicos. With travel restrictions, it was stuck there for almost two years. When he was cleared to come back and collect the boat in 2022, he brought along his girlfriend, Jayden Davila, for a three-month sail around the Caribbean. They docked in the Dominican Republic, Puerto Rico, the US Virgin Islands and the British Virgin Islands.
“John is a pretty peaceful person in general,” Davila said. “But there’s another level of peace and happiness for him when he’s on the boat. Even when there are issues—and something is always going wrong—he liked dealing with it. When things are calm, sometimes he’ll just randomly grab his guitar and start playing. It’s really a beautiful existence for him out there.”
Jaso still lives primarily in St. Petersburg, where he manages some investment properties. But he’s seldom in one place for a long time. This winter, he’s been snowboarding in Colorado and Wyoming. By the spring, he’ll be back on the boat.
“When you’re sailing, you’re going back to something primitive,” he said. “You’re removing yourself from the material world — this concrete, electronic world. And you’re returning to this sense of wonder. It’s the same sense you get when you’re holding a newborn baby, looking into their eyes, and feeling the world disappear around you.
“Sometimes it’s easy to forget that we all come from the same place. When you’re out there on the water, you remember.”