3 mistakes from recent history that are still affecting Guardians’ offseason plans

The Guardians front office under Chris Antonetti has developed a reputation for making shrewd moves. 

Whether it be acquiring Corey Kluber as an unheralded prospect or acquiring Kyle Manzardo for the ghost of Aaron Civale, there are countless instances where the Guardians seem to be one step ahead of the rest of the baseball world. 

But that doesn’t mean they’re perfect. 

While some of their missteps are pretty clear cut (their trade of Junior Caminero is a clear misfire), some of the mistakes they’ve made require a bit of a deeper look. 

Here are three of those mistakes that will dictate how the Guardians move this offseason. 

These Guardians mistakes are going to impact how things go this offseason

Trading for Luis Ortiz 

While the Guardians’ trade for Ortiz was beginning to look like a win as Ortiz found his footing during the 2025 season, it hit an obvious snag in July when he was placed on paid leave as a part of a sports betting investigation.

Now it looks like we may never see Ortiz pitch in MLB again, as both he and Emmanuel Clase were indicted on charges related to the scheme. 

But that doesn’t mean that either pitcher is out of mind, as the Guardians are still on the hook for both player’s salaries until MLB finishes its investigation. While we’re less than a year removed from the Guardians’ trade for Ortiz, they don’t have him in their rotation but are still on the hook for his salary (as of now). It's the worst-case scenario to end all worst-case scenarios. 

While the Guardians got some strong starting pitching across the final month of the season on their march toward the postseason, their pitching depth took a big hit thanks to Ortiz’s suspension. 

While there are plenty of intriguing pitching options available in free agency, it’s still a bit disheartening for them to be dipping back into the pitching pool less than a year after swinging their trade for Ortiz. 

Inability to acquire an impact outfielder 

Although the Guardians have been searching for an impact outfielder since the dawn of time, their inability to acquire one feels particularly acute this offseason considering Cleveland’s outfielders combined to hit just .226 last season. 

Chase DeLauter and George Valera are intriguing prospects who impressed in their first taste of MLB action last season, but it’s also important to tamper expectations about what they could do in 206. 

The Guardians have made some big swings in the outfield over the past two seasons by trading for Lane Thomas in 2024 and Nolan Jones in 2025, but neither of those moves ended up panning out.

Maybe Jones will end up putting it together in 2026, but his performance in his first season back in Cleveland left a lot to be desired. 

There are plenty of exciting outfield options available in free agency, but it‘s hard to believe the Guardians will break the bank for any of them. Although their outfield situation will be better than it was last season (it can’t be any worse), the lack of established options alongside Steven Kwan is tough to ignore. 

Failing to ink Kwan to a contract extension

Kwan has been a mainstay in the rumor mill since his name was first floated over the summer, and it seems like that buzz could reach a fever pitch this offseason as the trade market materializes. 

While the Guardians are under no pressure to trade Kwan, teams are going to keep calling Cleveland about Kwan while also putting pressure on the Guardians by leaking trade details through the sport’s insiders. 

At this point, it seems like the time for Kwan to ink a contract extension with the Guardians has passed and both parties are in the midst of a slow march that will end whenever Kwan eventually gets traded. 

Although it’s a bit different than the song and dance Guardians fans went through with Francisco Lindor, Shane Bieber and Josh Naylor considering Kwan has been outspoken about his desire to stay in Cleveland, it seems like the time for a contract extension has passed. 

This is going to be the story off the offseason, and it’s going to go away any time soon.