FORT MYERS, Fla. -- In the next couple of weeks, newly acquired Twins reliever Jay Jackson and his fiancée, Sam Bautista, will write checks totaling a few thousand dollars to send off to various organizations -- they’re still finalizing which -- as they start to give back to support other families like theirs.

Just before Christmas, they were able to get their son, JR Bautista Jackson, out of the hospital following a five-month stay in the neonatal intensive care unit (NICU) at the University of Utah after he’d been born around 14 weeks premature. Jackson spent off-days flying to Salt Lake City to steal moments with his family last year as he pitched to a 2.12 ERA in 25 games with the Blue Jays.

Jackson has quietly launched a clothing line called Team Jaxland, from which he sells hats, shirts, sweaters, pants and bags emblazoned with his personal logos and his slogan -- “In Smiles We Trust” -- with portions of the proceeds from each item sold being donated to NICU-related charities and/or hospitals.

This will be their first check -- the first, Jackson hopes, of many.

“I'm hoping that we get a lot more people to order stuff so that I can write a bigger check,” Jackson said. “We're just in the midst of doing a couple of things, but we're definitely going to send the proceeds that we've got [as] a way to benefit and help other NICU families. That's the main goal.”

The idea for the clothing venture dates back to Jackson’s days in Japan, where he played for the Hiroshima Toyo Carp from 2016-18 and briefly for the Chiba Lotte Marines in '20 as he tried to establish a consistent career foothold. It was actually Jackson’s barber in Japan who created the logo, and he started putting it on shirts.

People in Japan asked Jackson to sell the shirts, he said, and when he came back to the U.S., he figured it would be a fun creative outlet for him to come up with the clothing designs. As he’s gotten older, he’s grown to enjoy sketching to pass the time, so he likes to design the items himself, collaborating with artists and sending the drafts out to be refined.

“I'll just get in moods where it's either that or reading from time to time,” Jackson said. “I read a lot now. Just sketching. Just trying to keep creative juices flowing as I've gotten older and filling time instead of what I was used to doing back in the day, like partying was my thing. So it's just, as you've gotten older with kids, I just want to try to impact other people as much as I can, too.”

He hasn’t publicized the clothing line a ton (it’s unassumingly linked in his bio on X for now), so the scattered sales have come in Japan, from his friends and from some people in Canada, he said, where he looks to have been a beloved figure among many Blue Jays fans.

Why “In Smiles We Trust”? That stems from Jackson’s extraordinarily roundabout journey through baseball, with his first Major League free-agent contract finally coming this season, with the Twins, at age 36. His five partial seasons in the Majors -- 2015, ‘19, ‘21-23 -- have come with five organizations, with two stints in Japan mixed in. He hasn’t pitched more than 30 1/3 MLB innings in any one season.

“I've realized that I have to be happy in order to continue to play, to continue to impact other people, to continue to have fun at this,” Jackson said. “You have to be happy. You come to the baseball field and you're mad, you're not going to be around much longer, right?”

At one low point, Jackson said he prayed, wondering if baseball was actually what he was meant to do and would allow him to provide for a family. The next day, he said, his agent called him with a contract offer -- and he’s vowed to keep smiling ever since. That’s evident in the Twins’ clubhouse, where Jackson seemingly floats around and greets everybody with a wide grin.

“I was like, ‘I'm never going to take it for granted again,’” Jackson said. “I'm going to enjoy every moment and I'm going to try to be as positive and uplifting as I can in this baseball life. That's how it's been since then. Ever since then, I've just tried to enjoy it and make sure other people are enjoying it as well.”

Despite that strong 2.12 ERA in 29 2/3 innings out of the Toronto bullpen last year in mostly low-leverage work, he was left off the Blue Jays’ playoff roster. This opportunity with Minnesota, Jackson said, allows him a shot to check off one of those final career boxes: winning a World Series.

He’s one of few relievers in this Minnesota bullpen mix that could go multiple innings. He did that at times in Toronto last season, and he is prepared to continue to do so for the Twins. That’s something Minnesota currently lacks in the majority of its bullpen composition.

As Jackson does so, he’s grateful that his NICU experience is over, with JR at home with his other two children. He won’t need to take brief, stressful trips back to that hospital in Salt Lake City and have to say tough goodbyes to go do his job again.

Just before Jackson talked to the media for the first time in Fort Myers, his phone buzzed with a text from Bautista, reminding him again of the little guy back home whose experience these clothing sales are meant to honor.

“For some reason, since I've been gone, he's been waking up at the same time I do here, waking her up, so I feel kind of bad for [Bautista],” Jackson said. “But yeah, he's at home. He's getting better and better, so I'm looking forward to seeing him as much as I can.”

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