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Red Sox prospect Roman Anthony is in good company during the offseason

Roman Anthony played at three minor league levels in 2023, finishing at Double A.Salem Red Sox

In many ways, Roman Anthony had an absurd first full professional season. The 2022 second-round draft pick had one of the most impressive teenage seasons in the Red Sox system this century, hitting .272 with a .403 OBP, .466 slugging mark, and 14 homers in 106 games.

Even more impressively, that performance came across three levels, as he moved from Single A Salem to High A Greenville in June, then to Double A Portland for a season-ending 10-game stint, when he hit .343/.477/.543 with more walks (8) than strikeouts (6).

Anthony became the first Red Sox draftee to reach Double A before turning 20 since Dernell Stenson in 1998, when he was in his second full pro season.


There was an audacity to the speed with which Anthony progressed in 2023 — yet his willingness to reach for a high bar is less surprising when you consider the offseason company he keeps.

On Monday, former big leaguer Matt Holliday posted a video of Anthony working out with his sons, Jackson and Ethan Holliday.

Ethan, a high school junior, is widely viewed as the No. 1 prospect in the 2025 draft. If he ends up being taken first overall, he’d be following in the footsteps of his big brother.

Jackson was the No. 1 overall pick out of high school in 2022, and as a 19-year-old in his first full pro season in 2023, he outdid Anthony, dominating across four levels of the Orioles system and finishing in Triple A.

“It’s a super-fun group to be around,” Anthony said. “Surrounding yourself with people like that, that challenge you to be better and push you to be better in the offseason, it really makes playing the season that much easier because the offseason, you make the work a lot harder and then it kind of slows the game down in the regular season.”


Anthony said he has known Jackson for years. Anthony grew up in South Florida; Jackson lived in Jupiter (spring training home of the Cardinals) during part of his father’s playing career. The two went to neighboring middle schools.

Though Jackson moved to Oklahoma following his father’s retirement, the two remained in touch, a friendship that was easy to sustain as they crossed paths in high school showcase events. And Jackson invited Anthony to join him while training in the 2022-23 offseason.

“We always knew each other and followed each other through high school ball and played in all the events together, stayed in touch,” said Anthony. “We just kind of connected more and more over the years and then once we both got drafted, we just planned to link up in the offseason.

“We spent a lot of time last offseason together — pretty much the whole month of November [in Oklahoma], and then went out there after New Year’s. So I spent a lot of time with that family. Just an awesome family, great people. I can’t say enough good things about him and his family.

“He’s just an awesome kid, great guy to be around, super-motivated. He crushes it in the cage, crushes it in the weight room. It’s just fun having somebody like that. It’s great to be in an environment in the offseason where you have other people around you that push you to be better and that you can learn from.”


Jackson Holliday was the No. 1 pick in the 2022 MLB Draft.Steph Chambers/Getty

In addition to being around Matt, Jackson, and Ethan Holliday, Anthony said former National League MVP Cody Bellinger also joined the workouts in Oklahoma last year. Moreover, working out with the Hollidays also allows Anthony to spend time around the players and facilities of the Oklahoma State baseball team. (Josh Holliday, Matt’s brother, is the head coach of the Cowboys, and Matt serves on their staff.)

While Anthony started this offseason with several weeks in Fort Myers — where the Red Sox conducted an extensive fall instructional program for minor leaguers — he’s now back in Stillwater with the Hollidays. He’ll also spend time this offseason at Cressey Sports Performance in South Florida, giving him an opportunity to take live reps against established big league standouts.

“When all the big league arms and the big arms start to ramp up closer to spring training, that’s just five minutes away,” said Anthony. “I go over there, get my workout in, and then get to face some big league arms.

“You can’t really beat it. For me, I’m trying to challenge myself as much as I can, trying to move around a little bit in the offseason so I’m not just in one spot the whole time just doing the same thing repetitively.”

That pursuit of a challenging, varied offseason helped Anthony lay the foundation for a spectacular 2023 season — something he’s hoping to build upon in a 2024 campaign that will likely start in Double A but with the big leagues coming ever closer into view.


“It’s becoming a little bit more real,” Anthony said. “It’s everything you dream up. So for me, it’s just trying to get there as fast as I can and do my job and help to win and bring a championship to Boston.”

Alex Speier can be reached at Follow him @alexspeier.