The $38.5M star knows much better than most how quickly things can spiral in this game. After seven solid years with the White Sox, his 2023 season took a drop the moment Chicago dealt him to the Angels. In a matter of a few weeks, he found himself shifting teams again, landing with Cleveland.
What followed was rough: a combined 6.89 ERA with L.A. and 7.04 with the Guardians, plus a messy divorce off the field. For Giolito, the turbulence was not just professional, it was totally personal.
“It was crazy,” Lucas Giolito said, looking back. “I didn’t realize the impact it would have on me getting traded… my performance suffered, for sure. I was going through a lot during that period.” That experience made one thing obvious to the Red Sox righty, he is not eager to pack his bags so early again. “I don’t want to be traded,” he added firmly. “I really love it here. I want to help this team win games to the end. I’m really pulling for us here.” It is more than just words, his performances lately have backed up the sentiment.
Still, the journey to this mindset was not smooth. After signing a two-year, $38.5 million deal with Boston, including an opt-out clause that gave him some leverage, Giolito’s 2024 was a complete wash due to elbow surgery. Then came a hamstring strain in spring training 2025, delaying his debut until late April. When he ultimately returned, he struggled, allowing 44 hits and six home runs in his first seven outings. It was enough to shake up even a veteran. “You start to think, ‘Where’s my place in baseball?’” Giolito admitted.
But instead of coiling again, Giolito hit the lab with Boston’s coaching staff. Using biomechanical data, they refined his delivery and pitch mix. The outcome? Four straight strong outings to close June, during which he allowed just two earned runs in 25 innings. “We’re a team within a team,” Giolito said, pointing to Boston’s rotation. “We want to help each other out, help the bullpen, and help the team overall.”
That commitment goes hand in hand with the conditional clause baked into his deal. If Giolito logs 140 innings, his 2026 option jumps to $19 million. At 58 ⅔ innings presently, he will need to stay healthy and efficient. But he is not stressed about it. “Either it’s gonna happen or it’s not,” he said. “For me, the mindset is what’s in the present… when I get the ball, I want to give the Red Sox a chance to win each time out.”
For Boston, this is not just about a pitcher avoiding another trade deal. It is about a former ace clawing his way back to consistency, and doing everything he can to make sure the ghosts of the White Sox days stay in the past.
While the $38.5 million talent is determined to remain with Boston and finish what he started, not every high-profile name on the Red Sox roster is guaranteed to stick around, particularly if contract talks go sideways.
Red Sox are anticipated to trade Bregman if extension talks stall
Alex Bregman arrived in Boston with anticipation and experience, and through 51 games, he delivered both. Slashing .299/.385/.553 before a quad injury stopped his campaign, the former Astros slugger quickly reestablished himself as an All-Star-caliber contributor. But as productive as his bat has been, he is recovering from a calf strain. But the clock is ticking on his stay in Beantown for another reason. Despite signing a three-year, $120 million deal this past offseason, Bregman holds an opt-out after 2025, which has now placed pressure on the front office to act quickly or risk losing him for nothing.
Talks are reportedly ongoing between Alex Bregman’s camp, led by agent Scott Boras and the Red Sox brass. The 2 sides have publicly expressed a willingness to work out a long-term extension. However, a recent report by The Athletic’s Jim Bowden showcased that several MLB executives believe Bregman could be handed out if an agreement is not reached by the trade deadline. Franchises like the Tigers and Mariners are already circling, hoping to land a bat like Bregman’s, should Boston pull the plug.
There is no financial barrier blocking the way, either. The Red Sox cleared more than $250 million off the books by trading Rafael Devers, meaning they have the flexibility to meet Bregman’s value. But value is not just about cash, it is also about timing. If Boston’s playoff hopes fade before July ends and extension talks hit a wall, it would be logical to move Bregman now while his stock is high. It is a classic trade-deadline dilemma: extend the star or flip the asset.
Credit: The Sporting News
Lucas Giolito and Alex Bregman have made it clear that they enjoy playing in Boston, but enjoyment does not always decide a long-period future. If the Red Sox hesitate or lowball the offer, contenders with deeper pockets and more urgent postseason ambitions could swoop in. And just like that, a short but memorable Boston session might come to a premature end.
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