Revisiting notable Blue Jays trades from 2020 to 2022

Both were pending free agents that season, both cashed out in a big way as Semien signed a big deal with the Texas Rangers, and Ray ended up signing with the Seattle Mariners for a 5-year, $115 million contract. While Ray battled injuries and inconsistency, he ended up being traded to the San Francisco Giants, where he rebounded as an all-star in 2025.

As for Bergen, he didn’t last long in Arizona and was actually brought back to the Blue Jays in 2021. Despite a promising 1.69 ERA in 10 games with the club, he was designated for assignment and opted for free agency that winter. He signed a minor league deal with the San Diego Padres in 2022, but has not played professional baseball in over 4 years.

2021: Steven Matz traded for Sean-Reid Foley, Josh Winckowski, and Yennsy Diaz 

It feels like every few years now, Steven Matz is being traded to other teams. At the time of writing, Matz is currently on his fourth team since being dealt from the New York Mets organization in 2021. Trading for Matz was Toronto’s way of basically looking at depth to a rotation they were not too pleased with on paper.

The move saw Toronto sending three young pitching arms to the Mets for Matz. Once he came to Toronto, the southpaw brought some stability to the rotation and won a career high of 14 games, while also posting a career high 2.2 WAR. While his first half was a bit disappointing at a 4.69 ERA, he turned things around in the second half, finishing with a 2.49 ERA.

As for the three arms that were traded away, Winckowski and Diaz were the teams’ #29 and #30 prospects in 2020, while Sean-Reid Foley was the #9 prospect in 2019.

Winckowski was actually a part of the trade that sent Andrew Benintendi to the Kansas City Royals in the winter of 2021 and has appeared in 121 games across four seasons with the Red Sox, posting a 4.20 ERA. Yennsy Diaz only appeared in 21 career games with the Mets to the tune of a  5.40 ERA; he has not appeared in the majors since 2021. Sean-Reid Foley went on to appear in 50 games for the Mets across four seasons before being released in the winter of 2024. He signed a minor league deal with the Arizona Diamondbacks, but only appeared in 16 games with the Reno Aces in AAA.

He was released at the end of this season and recently signed a minor league contract with the Braves. Winckowski is now back with the Blue Jays on a two-year deal and will be on the shelf for 2026 as he recovers from an arm injury.

2021: Jose Berrios traded for Austin Martin, Simeon-Woods Richardson 

Without a doubt, this is the one trade everyone circles back to over the last several seasons. This was the trade that signalled the Blue Jays’ shift from rebuilding to contenders in 2021.

The Jose Berrios trade is still evolving for both teams as both franchises are moving in different directions. For the Jays, Berrios has been a mainstay of the rotation for the last few seasons in Toronto, but it’s not always been smooth sailing. A 4.09 ERA in five seasons for the team. Berrios has had some missteps in Toronto, from a tough 2022 to the infamous wild-card in Minnesota, which drew a lot of ire from the fanbase for that decision. Berrios and the Jays went through a bit of a turbulent end to the 2025 season, but the right-hander appears to be a key part of the club heading into 2026 as the club deals with injuries to its starting depth. Berrios is currently entering year five of a seven-year deal signed back in the offseason of 2021, but has an opt-out in 2026.

Austin Martin was the Blue Jays’ #2 prospect at the time of the trade, and eventually debuted in the big leagues in 2024. He hit .253 across 93 games in 2024 and hit .282 across 50 games in 2025. He’s still a young enough player who’s finding his footing in the Twins organization, which is entering a rebuild.  He spent most of his time ping-ponging between moving in the outfield and second base, but with the emergence of Lukas Keaschall, Martin can still factor into the team’s outfield as it’s looking to get younger.

As for Simeon-Woods Richardson, he emerged as a key arm of the Twins’ rotation in 2025 with a 4.04 ERA across 23 games this past season, and posted the second-highest WAR among pitchers with 2.2 behind ace Joe Ryan. It’s still a trade that’s evolving for both teams, but the Jays have really benefited from adding Berrios to the rotation.

2022: Anthony Bass and Zach Pop traded for Jordan Groshans 

One of the significant moves of the 2022 trade deadline was trading with the Miami Marlins.

Trading Jordan Groshans at the time was a steep price, as he was ranked #3 in the team’s farm system. However, Bass’ numbers at the time with the Miami Marlins were hard to pass on, as well as getting Zach Pop, who was a young arm that the team could get control of. Bass went on to pitch the remaining 28 games that season, posting a 1.75 ERA, allowing just five runs across 25 2/3 innings. It was mitigated by the disastrous outing in the second wild-card game against Seattle in 2022.

What followed was the controversy surrounding Bass’s comments on social matters, as well as a 4.95 ERA in 20 innings. He was released in June of 2023 and has not pitched a game in the big leagues since.

As for Zach Pop, the Brampton, Ontario native had some promise with his hometown ballclub, but he struggled across two seasons in 2023 and 2024, posting a 4.89 ERA. He was designated for assignment and since then, has bounced around from Seattle, New York, Chicago and now has landed on a minor league deal with Philadelphia.

2022: Whit Merrifield traded for Max Castillo 

A trade that came up out of nowhere, the Blue Jays added an infield bat to help at second base in Whit Merrifield.

The Blue Jays acquired Merrifield for RHP Max Castillo. Castillo was an international free agent arm that appeared in nine games for the Blue Jays and also started a pair of games before the trade. Castillo didn’t last long with the Kansas City Royals, last pitching for the club in 2023. He last pitched in the Mexican league back in 2025.

As for Merrifield, he was an all-star for the Blue Jays in 2023 and was ranked fourth on the team in RBIs while also leading the team with 26 stolen bases. After a successful campaign, he left to join the Philadelphia Phillies in 2024 and ended the season with the Atlanta Braves. Merrifield retired after the 2024 season and now stars on the 6ix Inning Stretch Podcast under the Nation Network.