How Red Sox Could Benefit From Roman Anthony-Jackson Holliday Connection

BOSTON — Roman Anthony and Jackson Holliday represent the best of the future in the American League East. The young players for the Boston Red Sox and Baltimore Orioles — both just 20 years old — possess plenty of talent and maturity beyond their age.

Holliday, who made his MLB debut for the Orioles at Fenway Park in April, holds a strong friendship with Anthony that dates back to their time growing up near Jupiter, Fla. From an even younger stage of their lives, the two talented ballplayers grew together on their own hopeful baseball paths.

“I think it’s just a reflection of his character,” Anthony told NESN.com on Thursday at Polar Park in Worcester. “He’s a great friend of mine. He comes from an awesome family. I spend a lot of time with them in the offseason. I’ve been lucky enough to be around him, his brother, all the other great people out there. They come to Jupiter where I live. He kind of grew up in the area. Just growing with him and being around him the last couple of years, especially since I’ve been drafted, him and his family have been so awesome to me.”

“Yeah, it’s awesome,” Holliday told reporters Wednesday at Fenway Park. “Especially being as good of friends as we are to have someone in the division and a team that we play pretty often. It’s really special. Hopefully he’s up here very soon.”

Holliday grew up with baseball in his blood. His father, Matt, won a World Series with the St. Louis Cardinals while making seven All-Star appearances across his 15-year MLB career. Jackson’s younger brother, Ethan, will soon join those ranks as a likely top selection in the 2025 MLB Draft. The family now resides in Stillwater, Okla., with a home fit to support the ultimate baseball family.

Anthony starred in his own right growing up around Jupiter, winning Gatorade Player of the Year in the Sunshine State. The Red Sox prospect currently plays for Triple-A Worcester, one step away from joining Holliday in the majors. Even in their time apart over the years, the young players consistently found themselves admiring each other’s game.

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“One thing people don’t really give him credit for is that even from such a young age, he grew up around the game, so he had such a great feel for the game,” Anthony said of Holliday. “Regardless of his size or what he was doing at the time. You just knew he was always going to make the routine plays and do what good ballplayers do. It was easy to see that he was a stud from day one. Growing up around that, he had great people around him.”

Anthony recently followed in Holliday’s footsteps. Just months after the Orioles infielder ranked as the top prospect in baseball, according to Baseball America, the Red Sox prospect took over that spot this week with the graduation of Tampa Bay Rays infielder Junior Caminero.

“I always thought he should’ve been way higher ranked than he was,” Holliday assessed. “I always thought he was such a good player and a complete hitter. Everyone always talks about his power, but I always thought he was a really complete hitter. When all the rankings came out, I was like, ‘I think Roman is a lot better than they’re making him out to be.’ It’s awesome to see him accomplish that. Very happy for him.”

Holliday sent a congratulatory text message in a group chat with his brother Ethan, Anthony and another friend. Ethan initially didn’t know why Jackson texted. Jackson informed him of Anthony’s accolade, sparking excitement for the group.

“It’s really cool to be able to share that with him,” Holliday shared. “Obviously, we’ve trained together for the last two offseasons, in Stillwater or in Florida. I just texted him, ‘Congrats.’ Nothing crazy.”

“I always thought he should’ve been way higher ranked than he was.”

Jackson Holliday on Roman Anthony’s top-prospect status

Anthony knows all about the hype and fanfare that comes with being one of the top prospects in an organization, yet alone the entire sport. He’s had every step of his followed over the last year alongside fellow Red Sox prospects Marcelo Mayer and Kyle Teel — commonly referred to as the “Big Three” of Boston’s farm system. Nevertheless, Holliday provides a great example of how to handle the spotlight.

“You’ve got fans, media and all that comes with that,” Holliday explained. “I think my advice would be to keep doing what he’s doing. Nothing really changes. The goal is to play in the big leagues. Just to have the No. 1 prospect is something to say you accomplished in the minor leagues. I think that’s something that I would say. I think he’s done a really good job handling himself and not putting too much thought into it.”

It’s one thing to watch elite young talent grow in the same division. It’s another to use the connective mindset to sharpen each other’s skills. That’s been the case for the Red Sox and Orioles phenoms over the last two winters, with Anthony and Holliday training at the latter’s home in Oklahoma. Extensive time in the batting cage under the careful eye of a successful MLB All-Star — Holliday’s father, Matt — creates an ideal environment for the young players to become even better — together.

“He’s a pretty good player, so I don’t have to pick him apart too much,” Anthony shared. “I kind of just keep my mouth shut. With someone like Matt there, he sees a lot of things. He’s great at what he does. You can see he had a great career himself. I’m just kind of a sponge when I’m there to information. I collect it all and listen. We’ll talk here and there.”

While the two will drive the Red Sox and Orioles, with tremendous young cores, into division competition for years to come, the established connection will only improve each side in Boston and Baltimore.

“Jackson’s an awesome teammate and he’s a great student of the game,” Anthony said. “He continues to learn each and every day. We learn so much from each other in the offseason. Training with each other and just talking about the game.”

Anthony continued: “We’ve gotten super close. I consider him one of my better friends. Just getting to see him and do what he’s done, tearing up the minor leagues and making an impact in the big leagues now and still be so supportive. We constantly text along the way, regardless of how busy he is or I am. It’s a great friendship that I don’t take for granted. I’m excited to finish up this season, head out there and get after it with him again.”

“It’s a great friendship that I don’t take for granted.”

Roman Anthony on his connection with Jackson Holliday

During those mornings in Stillwater, two of baseball’s best young talents grind their way toward improvement with the presence of each other to add just enough of a competitive fire. That spirit continues throughout the afternoon in looser environments, whether that’s on the golf course or the pickleball court, where Anthony admittedly conceded skills to the Holliday family.

“We just have fun,” Anthony said. “We go out there, there’s a few other guys out there. It’s just kind of this friendly, competitive environment that we have that I think is so important in the offseason. You surround yourself with people that are competitive and so good at what they do. That’s more of the reason why it’s so great more than anything else.”

Anthony added: “I’m excited to just go out there and share the friendship that we have. Hang out with the family and have dinner with his family. His wife, his brothers, his sister. There’s so many great people around there. I’m excited to see his whole family. Like we just mentioned, I’m excited to go golf with those guys.”

So, will the AL East duo be back together for more offseason adventures?

“Oh yeah, he better come back out,” Holliday said. “We have fun. We’ll definitely either go down to Jupiter or I’m sure he’ll come out to Stillwater.”

“I’m looking forward to that,” Anthony said. “I’m looking forward to when he comes to visit in Jupiter, but I’ll be out there. Don’t worry.”