As the 2024 MLB season winds down, another mediocre Boston Red Sox season goes by the wayside. The archrival pennant winning New York Yankees have opened their pocketbooks for Aaron Judge, Gerrit Cole, Carlos Rodon and many others, meanwhile the Sox have been stagnant since signing Trevor Story. In the second off-season under Chief of Baseball Operations and 2013 World Series champion Craig Breslow, things must change after the failed “full throttle” approach that was the 2023-2024 off-season. Even with top prospects Roman Anthony, Kyle Teel and Kristen Campbell slated to appear on the major league roster in 2025, holes still need to be filled if the Sox want to return to the postseason for the first time since 2021.
Main priority: Sign Jack Flaherty and or Max Fried
Last off-season, Boston signed Lucas Giolito to be at the front end of their rotation. Unfortunately, before the season could even start, Giolito partially tore his UCL and had season-ending Tommy John surgery. Giolito will start for the Sox in 2025 but has a player option for the 2026 season. Thankfully for Boston, Giolito was high school teammates with the free agent pitching tandem. They have remained close friends and even attended Flaherty’s start in game 1 of the World Series last Friday.
The right-hander was dominant for 5.1 shutout innings until Giancarlo Stanton took him deep on his final pitch of the night. Regardless of the one missed spot of the night, Flaherty turned heads as free agency looms. Splitting time between Detroit and LA this season, Flaherty had a career resurgence, posting a combined 3.17 ERA and a 5.11 strikeout to walk ratio. Before the postseason, it was expected that Flaherty would command about 18 million a year. After some stellar performances in October, it would be no surprise if he got more than expected.
Fried has been a Brave for his whole career, however it seems that both sides will be mutually parting ways once free agency begins. The lefty has had a criminally underrated tenure in Atlanta, overshadowed by the likes of Spencer Strider and Charlie Morton. With a career ERA of 3.07 and a WHIP of 1.16, the two-time all-star is expected to ink a deal that could be over 30 million a year.
If Giolito can convince his buddies that Boston will be a contender and a great place to play, either of these aces would be on the hill for opening day of 2025.
A more conservative pitcher option: Re-sign Nathan Eovaldi or Nick Pivetta
All signs point to two-time World Series champion Nathan Eovaldi entering free agency after two seasons in Texas. Nasty Nate always shows up when the lights are the brightest. Red Sox fans will never forget his heroic efforts in game 3 of the 2018 World Series. Eovaldi shoved for 6 innings of relief in the longest game in the history of the fall classic. The right-hander will get somewhere in the 27 million range this winter and a reunion with Boston does not seem out of the question.
Nick Pivetta has exceeded all expectations in his time in Boston and is the definition of a Red Sock. Since joining the team in 2020, Pivetta has started and come out of the pen. Pivetta turns it up as the weather gets colder, similar to Eovaldi. He went 4 shutout innings in the 13-inning classic against the Rays in the 2021 ALDS. The problem is that there may not be enough space in the rotation for Pivetta in the 2025 campaign. If he is willing to accept a long reliever role or a role at the back end of the rotation, he would be welcomed back with open arms to Boston.
Bullpen needs: Re-sign Chris Martin and a consistent lefty
Despite some injury and mental health troubles in 2024, ownership should not forget Martin’s efforts in 2023. The set-up man sported a 1.05 ERA and even earned CY Young votes. Liam Hendriks will be replacing Kenley Jansen in the closer role, however a reliable 8th inning pitcher like Martin is necessary for any team come October.
The left-handed options remaining in the Red Sox bullpen are nothing to write home about. Southpaws Brennan Bernardino and Zack Kelly had stretches where they were great last season, but also were both sent down to Triple-A after midseason struggles. A reliable late inning lefty would solve matchup problems late in the game. Lefties Tanner Scott, A.J. Minter, Brooks Raley and Kirby Yates are all available. If Boston can sign one or two of these hurlers, the woes the team ran into last season could be non-existent in 2025.
Bats: Give Tyler O’ Neill qualifying offer and sign Jose Iglesias
Hitting is not the problem for the Red Sox coming into 2025. Boston was in the top 10 of almost every hitting statistic and they will be returning most of that core plus the incoming prospects. Outfielder Tyler O’Neill is a free agent after a great lone season in Boston. After being traded from the Cardinals in the off-season, O’ Neill had 31 homers and an OPS+ of 132. The qualifying offer for the Canadian is just above 21 million, so if the Sox bring him back, they will have some decisions to make with prospects and older players. O’ Neill loves Boston and having him back would be amazing for the Lockeroom and the younger players.
It is unbelievable that Jose Iglesias was not on a major league roster in 2023. One of the most underappreciated players of the 2010s, Iglesias had an unforgettable year with a hit song and a comeback season. Candelita started his career with Boston and made a brief return to the team in 2021. Rookie Ceddanne Rafaela really slumped at the plate to end the season after playing every day for months. Adding an infielder like Iglesias would take a ton of stress off the young guys while also giving them a veteran presence at the same time.
This should go without saying, but the front office must pick up lefty killer Rob Refsnyder’s club option for 2025 unless he decides to retire.
Trades: Not Triston Casas or top prospects
Talks of an Alex Bregman for Triston Casas trade have circulated. The sample size that Casas has provided for Boston should not show the need for a trade. Bregman is a great player but acquiring him at the expense of this core seems silly. If anyone needs to be traded, it should be Masataka Yoshida and his contract. An arm could become available during the winter meetings, and the DH could be on the move.
The Boston Red Sox have a great chance to make a return to the playoffs in 2025 if they make the correct moves this off-season.