The Cleveland Guardians have several players they should try signing to contract extensions, but that's easier said than done.
The Cleveland Guardians have a number of players on their roster they’d love to make franchise cornerstones and count on for years to come. That said, extending a player can be easier said than done.
Here are three players the Guardians should try extending, but it won’t be easy.
Steven Kwan
Every day Steven Kwan gets closer to free agency, the more difficult it’ll be to extend the two-time All-Star and four-time Gold Glove winner. Still, it can’t hurt for the Guardians to try signing Kwan to a long-term deal to keep the homegrown star in Cleveland.
Since Kwan made his debut in 2022, he owns a .281/.351/.390 slash line while proving he’s one of the top defenders in MLB, too.
The Guardians and Kwan were able to come to an agreement on a contract for the 2026 season to avoid arbitration, but determining the 28-year-old’s long-term value may be difficult considering his injury history and his dramatic dip in production in the second half of the last two seasons.
Aug 30, 2025; Cleveland, Ohio, USA; Cleveland Guardians left fielder Steven Kwan (38) hits an RBI single during the eighth inning against the Seattle Mariners at Progressive Field. Mandatory Credit: Ken Blaze-Imagn ImagesGavin Williams
Last season, Gavin Williams finally blossomed into the pitcher the Guardians envisioned him to be when they selected him in the first round of the 2023 draft. After the All-Star Break, Williams logged a 2.18 ERA and a 1.43 WHIP.
With Williams on the rise and still only 26 years old, now is the perfect time to explore the possibility of an extension, but that won’t be easy.
Why? Because he’s represented by Scott Boras, and extending players isn’t typically the agent’s style. It would be great if the Guardians could lock up Williams as the team’s ace for the next half-decade, but that reality seems a little far-fetched right now.
Cade Smith
Cade Smith, who’s entering his third season, is still making league minimum, but he’s substantially outperformed that dollar value. The right-handed reliever has registered a 2.42 ERA and a 0.953 WHIP since his debut in 2024.
What makes Smith even more difficult to extend right now is that his value may only go up in 2026.
After Emmanuel Clase was placed on leave, Smith became Cleveland’s full-time closer. Now, that’s the role the 26-year-old will have heading into this season, which could only increase how much money Cade could demand for his next payday.