The oldest player in Classic history just can't quit the game he loves

March 8th, 2026
Art by Tom Forget
Art by Tom Forget

PUERTO RICO -- Watching taking swings under the setting Puerto Rican sun, it looks similar to how he looked during his star-filled seasons for the White Sox on Chicago's South Side more than 10 years ago.

It somehow looks similar to how he looked 20 years ago -- in the exact same place at Hiram Bithorn Stadium, in the very first iteration of the World Baseball Classic.

If you squint hard enough, it might even look similar to how he looked at 7 years old when he first learned the game of baseball. It was in a small neighborhood to the west of Havana called Taco Taco. His uncle taught him, a beloved relative who's now sick and Ramirez is taking care of. That uncle is part of the reason why Ramirez is still putting on a uniform at 44 years old. Also, there's a much simpler reason.

"I just love baseball," Ramirez told me through a translator. "I can't give it up."

Alexei Ramirez is the oldest player to ever put on a World Baseball Classic uniform, one year older than a 43-year-old Roger Clemens back in 2006.

He's also just one of three players in this year's tournament to have also participated in the '06 Classic -- joining the Netherlands' Shairon Martis and Panama's Paolo Espino. Back then, Ramirez was a little-known 24-year-old shortstop out of the Cuban National League. His performance in that league, and his performance at that year's Classic impressed MLB scouts.

Ramirez signed a four-year, $8 million deal with the White Sox in 2007, enjoying the best seasons of his career in the black and white.

He won two Silver Sluggers, went to an All-Star Game and endeared himself to the fervent Chicago fanbase for eight years. He had a couple quick stops in San Diego and Tampa Bay in 2016 and then, to most of us, seemed to just disappear at 34 years old. So, what has he been doing for the last 10 years? How has he stayed in shape to come back here and play in 2026?

For seven years after his final foray in the big leagues, Ramirez has played in a competitive Sunday sandlot league in Miami.

"They had a bit of everything -- a combination of kids, some American-based, some not," Ramirez said.

Oh, and the outfielder said he's also been dabbling in a sport we might play on a relaxing weekend. With a few beers in the cooler next to the dugout.

"I also play softball," Ramirez said. "Fast and slow."

Opposing teams react how you think they might react when they see former MLB All-Star Alexei Ramirez at the plate.

"Everybody is like, 'Oh my god,'" Ramirez smiled.

Of course, it hasn't only been beer league softball. Ramirez took a turn in the Mexican League in 2018 and then, in 2024, he went back to the Cuban National Series -- a circuit he first joined 24 years before at the age of 18. Ramirez, in his early 40s, was one of the best hitters in 2024-25 -- clubbing 15 homers with a .339 batting average and 1.082 OPS. The bat that scouts said "would play at any position" almost two decades ago was still playing.

Ramirez has also had some off-the-field obligations he's been dealing with the last few years.

"I'm taking care of my uncle and his family at the same time," Ramirez said, getting a bit emotional. "He's the one who first taught me baseball."

And now, almost full circle, the veteran is back in Puerto Rico where he played in his first, and the first, World Baseball Classic. Where his journey to stardom in the Major Leagues began. When he became a household name White Sox announcer Hawk Harrelson loved to scream.

"I'm very happy, I'm glad to keep playing," Ramirez said. "We have very young players now. I was talking to manager [German Mesa] before and he was saying the veterans -- he doesn't called them the veterans, he calls them the 'youth forevers' -- are very helpful for the young kids."

Nearly 30 or so years in organized baseball (slow-pitch softball can be very organized), will make you that helpful.