Baseball’s quiet season just ended. Free agency kicks off Monday night, and the clock is already ticking toward the Dec. 1 lockout. The Red Sox have a roster that looks decent on paper, but they face five tough questions before the players and owners sign a new deal. Chief baseball officer Craig Breslow has to fix the lineup and the pitching staff without wasting time. The team cannot wait until the rules change to make big moves. They need to act now while the window is open.
First, the front office must decide how busy they want to be. A recent analysis by The Boston Globe‘s Alex Speier showed that the Sox usually slow down their spending when a contract is about to expire. They wait for the new rules to be clear before making rich offers. But the pressure is high this year. The team needs to upgrade their slugging capability, and they cannot afford to sit on the sidelines. Although all players Breslow acquired at the trade deadline remain controlled through 2027, work still remains. The roster has holes that need filling right away.
Replacing Sonny Gray and Fixing the Rotation
The biggest hole in the pitching staff is Sonny Gray. The team officially let him go as a free agent Friday. He took a $10 million buyout after the club declined his mutual option. In 29 starts during 2026, Gray posted a 2.72 ERA and 1.15 WHIP, making him their top pitcher. That is a huge loss, even if Garrett Crochet comes back healthy. The Sox have to choose between calling up young arms like Brayan Bello or buying a replacement from the free agent market. If they want a solid number two starter, they might need to bring back Michael King, who is also a free agent this winter.
The middle infield is another puzzle. Trevor Story is entering the final year of his six-year, $140 million contract. He is due $25 million next season. If he starts the year slow, the team might have to look elsewhere. The organization cannot afford to pay a starter who cannot hit or field. This situation adds a layer of risk to the offseason plan. The front office has to weigh the cost of keeping Story against the risk of him struggling again.
What Willson Contreras Wants
First baseman Willson Contreras knows exactly what the team needs. William, his younger brother, secured a World Series title alongside the Milwaukee Brewers while he looked on. After that, he spoke to The Boston Globe’s Peter Abraham at Tropicana Field. At Tropicana Field on Wednesday, he stated to Peter Abraham of The Boston Globe, “I think we need some more offense.” Contreras had a great year himself, hitting 27 home runs with 81 RBI. He led the club in those stats, but the team still got outscored 18-2 in the Wild Card Series. He believes adding another bat is the only way to fix that problem.
When asked how to get that extra offense, Contreras pointed to the front office. “That’s for [Craig] Breslow to figure out,” Contreras added. The pressure is on Breslow to find a solution before the lockout starts. The team cannot rely on Roman Anthony to be a star right now, especially since he re-injured his wrist in the playoffs. They need proven hitters who can step in and help immediately.
The bullpen looks strong on paper, but age is a concern. Aroldis Chapman and Tyron Guerrero will be 39 and 36 next season. Chapman saved 35 games and had a 1.92 ERA, but durability is a worry. Garrett Whitlock is under control, but the team needs depth if injuries strike. The Red Sox have a good core, but they need to make sure it holds up for a full season. The next few weeks will define the team’s chances for 2027.
