The Boston Red Sox chose a middleground in 2024, making several veteran free agent additions while also carving out time for their younger players to gain experience. But the results were a third straight season without a playoff berth and now the team is left to fortify its roster this winter or risk extending that streak in 2025. One of the most impactful additions from last winter was Tyler O’Neill, who was acquired in a trade with the St. Louis Cardinals and ended up leading the Red Sox with 31 home runs. O’Neill is now a free agent following his final year of arbitration eligibility and the Red Sox will have to re-sign him or watch this year’s leading slugger join another team.

Zachary Rymer of Bleacher Report has predicted that O’Neill will reject a qualifying offer from the Red Sox, but ultimately re-sign with the team on a three-year, $45 million contract. “For their part, the Red Sox can ill afford to lose O’Neill’s right-handed thump,” Rymer added. “They should know that they stand to gain more from his pull power than most teams and that they have enough outfield depth to cover for him if he needs to DH more often.” As Rymer noted, O’Neill swung a critical right-handed bat for the Red Sox order in 2024. Teammates Jarren Duran, Rafael Devers, Masataka Yoshida, Triston Casas and Wilyer Abreu are all left-handed hitters. That profile, plus the outfielder’s surprising .241/.336/.511 slash line in one of the healthiest seasons of his career, make a strong case for a reunion with the Red Sox for next season and beyond.

“The Red Sox picked the muscular slugger up as a reclamation project last winter, yet even they might not have dared hope for the returns they got,” Rymer wrote. “O’Neill led the team in homers and was one of the five best pure power hitters in MLB.” Ultimately, the Red Sox have a lot of critical decisions to make this winter. In addition to O’Neill, Nick Pivetta, Chris Martin, Kenley Jansen, Lucas Sims, Luis Garcia and Danny Jansen are all set for free agency as well.

The front office will have to decide whether the team is ready to make a deep run now or if hedging toward the future is the more prudent route. In any case, a multi-year return for O’Neill could make sense.