As the Boston Red Sox attempt to get back on track following a brutal five-game start to the season, they’re going to need some key contributors to rise to the occasion.
This Red Sox team has generally done a good job of locking up the core, as Garrett Crochet, Roman Anthony, Ceddanne Rafaela, and Brayan Bello are all on team-friendly extensions. But there are still members of this team who can help themselves and the club by earning a big payday this year.
Let us therefore discuss the three players on the Red Sox who could most realistically earn themselves a big new contract with a standout season.
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1. Starting pitcher Sonny Gray
Gray was a layup for this list, as he’ll turn 37 next season and will be coming off a backloaded three-year deal that guaranteed him $41 million this year when accounting for the buyout on his mutual option. And mutual options never realistically get accepted, so Gray is 99.9% certain to become a free agent.
If he pitches for most of the season like he did on Saturday, he won’t find it easy to get paid. If he turns it around and strikes out 200 batters for the second-straight season, he’ll get the bag, and probably not from Boston, which has a bunch of top pitching prospects to work into the mix.
2. Outfielder Wilyer Abreu
Mar 30, 2026; Houston, Texas, USA; Boston Red Sox right fielder Wilyer Abreu (52) reacts after striking out during the second inning against the Houston Astros at Daikin Park. Mandatory Credit: Troy Taormina-Imagn Images | Troy Taormina-Imagn Images
If the Red Sox were truly gung-ho about extending Abreu, they likely would have done it by now. And if he plays well enough to merit a long-term deal this season, his price tag might be too high to consider signing whatever offer sheet the Red Sox have in mind.
That said, Abreu looks like he could wind up leading this team in a boatload of offensive categories this year, and even though the Red Sox have him under control through his age-30 season, an extension is never out of the question when someone proves to be a piece of the core.
3. Starting pitcher Connelly Early
Mar 29, 2026; Cincinnati, Ohio, USA; Boston Red Sox starting pitcher Connelly Early (71) pitches against the Cincinnati Reds in the first inning at Great American Ball Park. Mandatory Credit: Katie Stratman-Imagn Images | Katie Stratman-Imagn Images
Much in the same vein as Abreu, Early is out to prove that he belongs in the mix long-term. The Red Sox have lots of guys with less than two years of service time, but Early, who hasn’t even hit the 50-day mark yet, feels like the most realistic extension candidate.
Infielders Marcelo Mayer and Caleb Durbin, fellow starter Payton Tolle, and catcher Carlos Narváez fit into the same category.