3 Craig Breslow contracts that already seem to be blowing up in Red Sox’s face..
The Boston Red Sox haven’t had the easiest go of things recently when it comes to signing free agents or extending players.
Trevor Story and Chris Sale immediately come to mind when fans think of Sox contracts that haven’t worked out, but the Red Sox have a few current deals that may be taking a turn for the worse. Chief baseball officer Craig Breslow had to take some risks in 2024 because the front office didn’t give him enough money to spend on top tier players.
Boston’s spending philosophy changed in 2025 after it signed Walker Buehler and Alex Bregman, but it’s still stuck with some contracts that could’ve gone better. Luckily, there’s still a chance these players still have time to pan out for the Sox.
3 Craig Breslow contracts that already seem to be blowing up in Red Sox’s face
Liam Hendriks
Before the 2024 season, the Red Sox signed Liam Hendriks to a two-year deal as he recovered from Tommy John surgery. Boston expected Hendriks to be ready to join the big league team late in the second half of the season, but multiple delays in his recovery kept him on the shelf.
This spring training, Hendriks is fully healthy but hasn’t bounced back to his old self. He’s allowed six runs, two of them homers, with three strikeouts in four innings of work in the Grapefruit League. Four innings is a small sample of work, but at this rate, Hendriks is at risk of losing out on Boston’s closer job (subscription required).
Lucas Giolito
The Red Sox signed Lucas Giolito as a rebound candidate after two consecutive rough seasons in 2022-23, but it hasn’t gone as planned. The veteran made a few spring training starts in 2024 before finding elbow issues, and he underwent the internal brace procedure, which kept him on the injured list for his entire first season with Boston.
Now, Giolito will begin the 2025 season on the IL. He strained a hamstring during his first spring training start after his recovery. Thankfully, Giolito’s elbow is fine and initial reports on his condition said he didn’t need to be shut down from throwing, but the Red Sox haven’t supplied a timeline for his return yet. His injuries aren’t his fault and no one could’ve predicted them, but so far, Giolito’s contract hasn’t worked out for Boston.
Brayan Bello
Brayan Bello is listed here on a sort of technicality, but recent circumstances have raised relevant conversations. The Red Sox signed Bello to a six-year, $50 million extension before the 2024 season as the team hoped for a breakout from one of its few homegrown pitchers. He didn’t break out, but Bello posted 4.49 ERA over 162.1 innings and a career-high 30 starts. His stats don’t jump off the page, but his second half was much better than his first and signs of improvement are definitely there (5.32 ERA in the first half, 3.47 ERA in the second.)
The Red Sox recently announced that Bello will begin the season on the IL due to shoulder soreness. His delayed start and underwhelming 2024 season would’ve been softer blows if the Sox were paying him the arbitration salary he would be owed if he wasn’t extended last year. Bello’s contract is team-friendly and still has plenty of time to pay off, as he’s just 25, but so far, he’s been more pricey than necessary.
