Potential contract extensions for the Guardians

After last season’s contract extensions for Emmanuel Clase, Myles Straw, and José Ramírez shortly before the season, time is ticking for the Guardians front office to lock down some of their young talent before the season starts again. Will we see any extensions this spring?

Let’s take a look at some of the potential candidates on the team.

That ship has sailed

Amed Rosario, 27, free agent after 2023 season (represented by Octagon)
I cannot see a scenario, given the length and size of contracts given out to shortstops in free agency this offseason, where Amed Rosario signs an extension to stay in Cleveland. I know José Ramírez and Terry Francona love him, but it doesn’t make sense for a team that has been drafting and developing young and talented shortstops for the past six years to commit $15-20 million a year, at least, to a player who is 27 years old.

It doesn’t make sense for Amed Rosario not to try the market where, as the best shortstop entering free agency, he can try for a deal north of $20 million in average annual value that would take him well into his mid-30s.

Shane Bieber, 27, free agent after 2024 season (represented by Rosenhaus Sports)
In a just world, Cleveland would offer Shane Bieber a 7-9-year, $180-$200 million contract ... and Bieber would accept because he recognizes that climate patterns are going to make his hometown on the West Coast less temperate than sunny Northeast Ohio. Cleveland’s new owners would then commit to spending at least $120 million on team payroll per year.

There’s snow in the 10-day forecast in March in Ohio in case you haven’t noticed, so we clearly don’t live in a perfect world. As long as the Guardians are hanging at or below $100 million in payroll, I don’t see them handing out contracts that long and that expensive to volatile assets like pitchers.

I also don’t see why Bieber, given that Yu Darvish just got a 6-year, $108 million contract at the age of 36, would not just hold out to test his value on the open market. Personally, Bieber convinced me in 2023 by remaining a top 10 pitcher in MLB with diminished velocity that he is the kind of pitcher a team should gamble on providing great value into their late thirties, but I also acknowledge that this year will likely be peak Shane Bieber, if we haven’t already seen it.

Bieber isn’t signing an extension here ... unless Santa Blitzer comes through with a really early gift — maybe on March 25!

ANYTHING IS POSSIBLE!!!!!

Bo Naylor, 23, free agent after 2029 season (represented by ISE)
The Guardians may be well-served to take an example from the playbook of teams like the Braves and Rays and lock up a young superstar before he even takes the stage. I don’t know how the Guardians view Bo Naylor, internally, but if they believe in his future as a starting catcher on a playoff team, offering him a deal that pays him through his arbitration years and tacks on 2-3 more could be an inventive way to keep a 20-20 catcher in Cleveland past the date they would usually have to consider trading him.

Unlikely ... but interesting

Josh Naylor, 25, free agent after 2025 season (represented by ISE)
If Josh Naylor hadn’t suffered that severe ankle injury in 2021, he would be at the top of my list for an extension. There is so much to like in his passion and personality, as well as a 121 wRC+ last year and an aptitude for big moments that has been visible from the moment he set foot in Cleveland’s clubhouse.

Naylor is not perfect, of course — his defense is limited, to say the least, and he has not hit left-handed pitching at all as a major leaguer (though he was decent against lefties in the minors). But, that’s precisely why a modest extension with Cleveland would see possible ... the Guardians could buy out Naylor’s arbitration years and tack on three years to get him into his thirties. But I doubt that they will offer this kind of deal until he has at least another year to show that the ankle is trustworthy, and who knows if even that would be enough to give them enough certainty to make a long-term commitment to a player who represents a significant risk of tying up their DH position if something goes even a little awry.

Aaron Civale, 27, free agent after 2025 season (represented by Jack Toffey)
Again, it is primarily injuries that make me skeptical that the Guardians would pursue an extension with Aaron Civale. His strikeout numbers climbed and walk numbers lowered last year. He exhibits an excellent work ethic and throws a bazillion pitches (give or take).

All of this seems like the kind of pitcher the Guardians could, theoretically, look at taking into his early thirties as they did with Corey Kluber and Carlos Carrasco (yes, I know both were much better pitchers than Civale when they were extended — this would be a younger pitcher for a cheaper price). If the Guardians believe in the player they have developed in Civale, an extension would be a reward for a player who has bought into their gameplan, setting a great precedent for future pitchers working their way through the farm system: If you do the work, you will reap the reward.

Alas, Civale’s frequent injuries as a starter over the past couple of years make this extension a virtual non-starter.

I’m listening

Triston McKenzie, 25, free agent after 2026 season (represented by Octagon)
As I think about the potential of a possible extension, I am intrigued by the idea of offering Triston McKenzie, who struggled to get healthy during his time in the minor leagues, the security of a long-term deal, thereby ensuring a player who has flashed ace-of-the-staff potential will take his shot at reaching his ceiling in Cleveland.

Buying out McKenzie’s arbitration years and tacking on 2-3 more seasons seems like a deal that would be mutually beneficial for both sides if they believe in him. However, as long as the Guardians believe in their ability to draft and develop starting pitching, they may not be motivated to extend pitchers whom they already control until their age 29-30 season (an age at which many pitchers tend to decline).

I’d give Dr. Sticks a lifetime deal if it were up to me, but I suspect McKenzie will bet on himself and pass on the kind of discount it would take for the Guardians to keep him here for 6-7 years.

Cal Quantrill, 28 years old, free agent after 2025 season (represented by Excel)
Cal Quantrill is already a Guardian through his age 30 season, so I think an extension would look like getting a firm number for his arbitration years and tacking on two years — maybe with a team option or two.

I mention Quantrill primarily because he is always mentioned by players and media as a leader in the clubhouse and he seems set to be a workhorse who provides his team a chance to win every time he takes the mound. Despite being spoiled by a great pitching development system here in Cleveland, I think it’s important to remember that players like him don’t grow on trees, and he’s got a solid floor to rely on even if he does decline at thirty years of age as some pitchers do.

Ultimately, I think Quantrill is about one year too old for the Guardians to offer terms to which the right-hander would agree, but it doesn’t stop me from dreaming that he can be a Cleveland legend for his whole career.

Strike while the iron’s hot

Steven Kwan, 25, free agent after 2027 season (represented by CAA Sports)
Again, Steven Kwan finds himself at a great age where he will just have turned 30 during his last year of team control. That is the perfect space where a contract that buys out his arbitration years and adds 3-4 years, even, makes a lot of sense.

The issue with Kwan is that he is unlikely to be a great choice as a DH bat, so you’re relying on him to stay healthy enough to stay on the field. This is the bet with any extension, however, and Kwan has such an elite skill in being able to make contact that it makes perfect sense to me for the Guardians to go to him and see if he has interest in signing a deal to keep him hitting leadoff in Cleveland into his 30s.

Put Kwan right next to José Ramírez (and add Triston McKenzie while you’re at it!) as the faces of the franchise and let’s ride.

Andrés Giménez, 24, free agent after 2026 season (represented by Rep1 Sports)
Giménez had the best breakout year in a season with a lot of breakouts for the Guardians, with a gold glove at second base and a 140 wRC+ at the plate.

If Giménez and his agent believe that this is his norm, I think the possibility of an extension has probably already passed. However, I suspect that Giménez and his representation may value the idea of security that could take him into his 30s. The Guardians are still going to have to pay significantly for him unless they can pull some kind of Braves/Ozzie Albies magic.

The Guardians and Giménez should definitely engage in some thorough extension talks this spring either way. Dan Szymborski projected six years and $55 million would make sense for Giménez. I suspect it takes slightly more in average annual value (maybe $12-14 million per year?) and at least one more year, or team option, to get it done.

Bottom line

With uncertainty over their regional sports networks and ticket sales still rebounding from COVID and whatever effects the name change may or may not be having with the Cleveland faithful, it wouldn’t surprise me to see Cleveland hold off on aggressively pursuing extensions until that situation is resolved, which would put extension talks off until the fall unless a player is absolutely desperate to remain in Cleveland.

One factor Cleveland should consider is how contracts ballooned this offseason. It will happen again after the next lockout following the 2026 season. Getting some guys under contract through 2027, even if it’s for a little more than what the team is comfortable with, is likely a great way to save money in the long run. The team has to choose the right players to minimize the payroll flexibility they may lose, depending on the philosophy of the ownership group, if they extend a player who declines significantly.

Personally, I’d extend the whole bunch of lovable guys we call the Cleveland Guardians, but since I don’t pay the bills, all I can do is speculate that at least one of the names above may get extended before the regular season begins.