Ranking the 5 most transformative trade deadlines in Guardians history since start of 2020

This year’s trade deadline was a Chris Antonetti masterclass. Although the Guardians’ roster is still flawed, it’s much less flawed than what it was a week ago and finally has the kind of power potential that it’s been missing all season along with some more pitching depth. 

Even though the Guardians entered play today three games behind the White Sox in the American League Central, the team’s decision makers still seem to think the Guardians have a chance to make some noise in the wide-open American League. 

“I think our front office did everything that we could have ever wanted from them,” catcher Austin Hedges told MLB.com’s Tim Stebbins. “Two impact bats and an impact starter. That's all you can ask for.”

But where does that masterclass rank among the new era of Guardians baseball? Let’s take a trip down memory lane. 

Guardians’ 2026 trade deadline is one of the team’s best

Honorable mention(s): 2022, 2025

While these two trade deadlines didn’t make the list, it’s still worth mentioning them for the moves (or lack thereof) Cleveland’s front office made.

The Guardians sprinted out to a huge lead in the American League Central in 2022, and the only “move” they made at the deadline that year was trading catcher Sandy León to the Twins. 

They also optioned Franmil Reyes to the minors, which was the beginning of the end for the ‘Franimal’ in Cleveland. 

Cleveland didn’t do much at last year’s trade deadline either (their lone moves were trading Shane Bieber and Paul Sewald), despite receiving a ton of trade interest in Steven Kwan. 

Now, onto the top five…

5.) 2021

Indians acquire LHP Konnor Pilkington from Chicago White Sox for 2B César Hernández
Indians acquire 1B Pablo Sandoval and cash considerations from Atlanta Braves for OF Eddie Rosario
Indians acquire OF Myles Straw from Houston Astros for Yainer Diaz and Phil Maton
Indians acquire LHP Peyton Battenfield from Tampa Bay Rays in exchange for DJ Johnson and Jordan Luplow 

The 2021 iteration of the Cleveland Indians was an odd one. It was the first year of the post-Francisco Lindor era, and the year before the Guardians rebrand that was followed by a magical season.

Although the Indians ended that July with a 51-50 record, the front office recognized they didn’t have a winning roster and pulled off a soft sell. 

Straw played well in his first stint with the Guardians but immediately became a depressed asset thanks to his five-year, $25.5 million extension. Meanwhile, Maton has become a bonafide MLB reliever and Diaz has largely played well for the Astros. 

Still, the rest of this isn’t much to write home about. Rosario went on a heater for the Braves in the 2021 postseason, but his struggles in Cleveland became too much to ignore. 

4.) 2024

Guardians acquire OF Lane Thomas from Washington Nationals for LHP Alex Clemmey, SS Rafael Ramirez Jr. and INF José Tena
Guardians acquire RHP Alex Cobb from San Francisco Giants for LHP Jacob Bresnahan and INF Nate Furman

The Guardians had a huge lead in the American League Central at the time of the 2024 deadline, so Antonetti and Co. decided to fill the team’s biggest needs by acquiring a right-handed hitting outfielder in Thomas and additional pitching depth in Cobb. 

Although Thomas’ time in Cleveland was a bit of a disappointment because of injuries, he still recorded one of the marquee moments in recent Guardians history when he crushed a go-ahead grand slam against Tarik Skubal in the 2024 American League Division Series. 

The deal for Cobb was an outright disaster. Not only did he make just five appearances with the Guardians due to injuries, but Bresnahan is one of the top prospects in San Francisco’s system and Furman just made his big league debut.

3.) 2023

Guardians acquire 1B Kyle Manzardo from Tampa Bay Rays for RHP Aaron Civale
Guardians acquire RHP Noah Syndergaard from Los Angeles Dodgers for SS Amed Rosario
Guardians acquire OF Kahlil Watson and INF Jean Segura from Miami Marlins for 1B Josh Bell 

While the Guardians’ trades of Bell and Civale nearly tanked their clubhouse, they’ve both become one of the shrewdest deals in recent team history. 

Although Manzardo was just demoted to Triple-A, he has provided the Guardians with some power production while Civale had a disastrous tenure with the Rays and has bounced around MLB since. 

The same can be said for their trade of Bell. Watson was regarded as an immature prospect at the time of the trade, but he grew into one of the best prospects in Cleveland’s system while learning the outfield.

He made his big league debut earlier this year and seems to be a part of the team’s long-term future. These trades were maligned at the time, but they both turned into wins.

2.) 2026

Guardians acquire RHP Craig Yoho and OF Blake Perkins from Milwaukee Brewers for C Bo Naylor and RHP Codi Heuer
Guardians acquire OF Jo Adell from Los Angeles Angels for C Jacob Cozart
Guardians acquire LHP Foster Griffin from Washington Nationals for LHP Will Dion, LHP Josh Hartle, RHP Kendeglys Virguez and OF Nick Mitchell

That brings us to this season. 

While there’s still plenty of time left for this deal to age one way or another, the Guardians’ aggressiveness at the deadline was an exciting development given how wide open the American League is. 

Adell fills the team’s hole against left-handed pitching, while Griffin adds some more depth to a pitching staff that was one injury away from imploding. Heck, even the addition of Yoho and Perkins for two fringe players looks like a clear win. 

Plus, Griffin’s the only rental from this group, so these moves were about the future as much as the present. 

1.) 2020

Indians acquire RHP Cal Quantrill, 1B Josh Naylor, C Austin Hedges, INF Gabriel Arias, INF Owen Miller and LHP Joey Cantillo from San Diego Padres for RHP Mike Clevinger, OF Greg Allen and RHP Matt Waldron

And there it is. 

While the 2020 season was truncated, Cleveland’s front office still found a way to change the franchise’s trajectory by pulling off one of the greatest fleeces of all time. 

Naylor ended up becoming an All-Star, Quantrill was a solid mid-rotation starter, Hedges is a Cleveland legend and Arias and Cantrillo are still on the roster. 

Meanwhile, the Padres got just 27 starts from Clevinger and a single at-bat from Allen. 

It didn’t take long for this trade to become a win for the Guardians, and it’s become more of a win as the years have gone on. 

Thanks, A.J. Preller.

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