Spring Training feels just around the corner which leads us to a perennial topic in Cleveland baseball offseasons: who, if anyone, will Cleveland ink to an extension? In recent years they signed Emmanuel Clase & Andres Gimenez to extensions, both of which feel like good bets to pay dividends for the club long term with Clase leading the American League in saves two years in a row, and Andres Gimenez posting 5.3 bWAR and winning a Platinum Glove. They also signed Myles Straw and Trevor Stephan to extensions which appear…less lucrative for the club with both struggling mightily since signing deals. Nevertheless, extensions remain a vital tool in the front office’s toolbox to ensure the long term health of the franchise with stars like Corey Kluber, Carlos Carrasco, & C.C. Sabathia all signed with the club long term, and provided value over their contracts and as trade pieces later in their careers.
A Long History of Extensions
Inking players to extensions before they hit free agency remains a hallmark of Cleveland front office strategy since Hank Peters assumed control of the franchise in the late 1980s. Jim Thome signed a lengthy extension to stick in Cleveland through the 2001 season in the mid-90s to help extend Cleveland’s core, as did Omar Vizquel (twice). Later, Cleveland signed C.C. Sabathia, Cliff Lee, Victor Martinez and Travis Hafner to extensions too. The deals provided cost certainty to young players who, frequently, did not make significant sums of money in the draft or in arbitration while providing Cleveland with cost controlled players for longer. The deals worked out for Cleveland in two ways:
First, they allowed Cleveland to build stronger franchises over a longer period of time. The 2007 club, for instance, depended on extended players like Victor Martinez & C.C. Sabathia to anchor the team.
Second, they also granted Cleveland more time to flip players at the end of their contracts for more prospects. Sabathia, Martinez, Lee and (later) Kluber were all traded during their extensions for crucial players of future clubs including: Michael Brantley (Sabathia), Justin Masterson (Martinez), Carlos Carrasco (Lee) and Emmaneul Clase (Kluber).
This makes extensions an important team building tool in the front office toolkit.
Typically extensions are broached and signed during spring training with most deals announced sometime in March before the season begins. Rarely the work in Spring Training will result in a deal later in the year, such as the case of Travis Hafner’s 2007 extension (which…did not work out well for Cleveland in the long run). This tactic has spread throughout the league with the Atlanta Braves becoming particularly adept at inking their stars to cost controlled contacts. The Braves currently boast an impressive array of stars, nearly all of them signed to lengthy contracts in their ‘20s most of them paying far less than what free agency would bring had they declined to sign, and performed comparably.
Candidates for Extension?
The Guardians already signed Jose Ramirez, Emmanuel Clase, Andres Gimenez and Myles Straw to extensions, keeping all of them under team control through at least 2026, and with team options which can keep all of them under contract through the 2028 season. Andres Gimenez will earn over $20M in Cleveland in 2029 (assuming he is not traded before then, which is obviously not guaranteed). That leaves plenty of players as candidates for an extension.
Josh Naylor
The idea of Josh Naylor sticking around in Cleveland at least until when his brother Bo is eligible for free agency carries appeal. Josh is young, dynamic and charismatic providing Cleveland with another cornerstone to build around. He is also coming off a career season batting .308/.354/.489 (OPS+ 133) with 17 home runs and 97 RBIs, clearly the best offensive player Cleveland boasted in a down 2023 season.
That being said, there’s also plenty of reason why Cleveland would not want to sign Josh to an extension. To start: he’s a first baseman, and one with injury risk stemming from his knee he injured in a gruesome accident a few years ago (which was bothering him as recently as October of last year). His limited athleticism, and injury history, offer some risk that Cleveland typically avoids. Furthermore, Josh is only two years away from free agency, which would be later than Cleveland typically likes to extend players, and they already have at least one in house replacement with Kyle Manzardo.
For me there’s a couple major questions to ask. First, since Josh is so close to free agency and is coming off his best year: he’s likely going to cost a premium. Why would Josh sign a team friendly deal now? If he posts even one good season between now and free agency he’s likely to earn a deal at least as lucrative as what Cleveland will likely offer him in an extension now? If he posts two he’ll almost assuredly earn more. Second, since he will likely carry a premium, can Cleveland even afford to sign Josh? Payroll hit over $90M this year and, according to all sources, were scraping the barrel to even bring on limited additions like Austin Hedges (one year, $4M signing) to the roster. Can they really afford to pay Josh $10M+ in that environment? I tend to think not; especially with Manzardo waiting in the wings.
Frankly, given how little payroll flexibility I am not sure I want Cleveland to sign Josh Naylor to an extension. Not that I don’t want Josh to stick around: I do, but this roster is not good enough as constructed to win a World Series, and if I had to choose between them keeping Josh for another year and using the cash to improve the roster, or locking him up: I’ll gamble that they can spend the money better elsewhere.
Steve Kwan
Kwan is another fan favorite who, unlike Josh, posted a somewhat down year in 2023. He was fantastic in 2022 batting nearly .300, winning a Gold Glove, and becoming one of the most dynamic leadoff hitters in baseball. He struggled a bit this year but still won a Gold Glove. We know Kwan already rejected an extension offer from Cleveland (reportedly a similar deal that Myles Straw signed, 5 years $25M). I tend to think Cleveland won't dramatically increase their offer after Kwan’s comparative struggles in 2023.
Now, I would also add: Kwan’s skillset is one that is typically not as rewarded in free agency and arbitration than Naylor’s. This means there’s less value in Cleveland buying out his arbitration years and that his free agency years are not worth as much to lock up either. All of which tells me, of the upside we can gain by extending a player: Kwan’s is amongst the lowest. Extending Kwan is basically gambling that Kwan develops more skills, particularly power, or that you plan on moving him to center field. With Myles Straw locked up the latter seems unlikely, and while I like Kwan, I am content to play it by year.
Kyle Manzardo
I know, we have not yet even seen Manzardo yet, and he has not even finished a full year in AAA. However, signing your prospects to extensions before they even debut is becoming more common. Philadelphia did it with Rhys Hoskins, and Detroit & Milwaukee just inked their top prospects to deals before they are scheduled to debut this year. So why not Manzardo? Answer: because Cleveland does not appear ready to even start Kyle on their Opening Day Roster.
I am all for an extension of Kyle. If the team will not take risks in Free Agency or via trade, then signing your youngest players to cheap extensions is the easiest way to build your team cheaply, while taking some kind of risk (the risk that Kyle does not hit). But if the team can hardly stand to risk playing Kyle Manzardo, I cannot fathom them paying him for the privilege of playing in Columbus.
Bo Naylor
Bo is a more stereotypical candidate for an extension. He posted an intriguing rookie campaign of both struggles and successes. While you can see the star potential: he did not hit on all cylinders just yet. Bo is also younger than both Kwan and Josh (Bo will not turn 24 until this October), which means there is more prime seasons in reach. This, to me, makes Bo the ideal candidate for an extension. There is more upside, since we may not have seen the best of Bo Naylor yet, more cost certainty to lock in, and (since he’s younger) more potential prime years available to extend into than either Kwan or Josh.
If there’s a position player we extend: I hope it’s Bo.
Tanner Bibee
I will end with Bibee. Like Bo, he is the kind of player Cleveland tends to lock up. He just debuted and posted a good season (he finished 2nd in the AL Rookie of the Year balloting), and had he pitched all year could potentially have challenged Gerit Cole for the Cy Young Award. He also just gained a full year of service time which places him one year closer to free agency. He’s exactly the kind of guy Cleveland needs to stick around for a long time, preferably on a cost controlled contract, to return to the top of the AL Central.
Then again, all the reasons why Cleveland would want to extend him are the same reasons why he would not sign. He finished 2nd in the Rookie of the Year voting, which means he’s closer to free agency (and a big pay day). He was not just good this year, he was really good, which means he just needs one solid year to make a lot of money in arbitration before the 2025 season. This means Cleveland has far less leverage with Bibee than your typical rookie, and it will be more difficult to sign him.
That being said: Scott Boris represents Gavin Williams, and Logan Allen is nowhere near as talented. If there’s a pitcher Cleveland should try to extend to anchor their rotation for the next decade (or close to it): it’s Bibee. Yes, it will cost more, but Cleveland also does not have anyone in the system realistically poised to replicate Bibee’s results. They need Bibee, and he is the most urgent extension candidate on the team (in my opinion).
Outlook
Unfortunately if I had to guess Cleveland likely signs nobody this year to an extension. Basically every candidate for an extension carries a level of risk. I struggle to see Cleveland committing to going into what could be another lost season. Cleveland tends to get more aggressive with extensions in the middle of contention windows, not before they begin or after they end. It’s not clear to me that Cleveland views itself as a viable contender right now, nor do I think that they view themselves as serious contenders in 2025.
Furthermore, while they do have many extension candidates on the roster, each has risks or leverage over the team which makes this Spring Training less than ideal to approach any of them about playing long term on the North Coast. Which leads me to believe that the Front Office will not be calling a press conference to announce an extension in Spring Training or before the year starts in Oakland this March.
It’s been a weird offseason, and I think it will be a weird Spring too. But if they do announce an extension: I think our best bet is actually Bo Naylor, and I hope he’s who they pick.
-Benjamin, J