Blue Jays Agree to Minor League Contract With Josh Winckowski

[Leo Morgenstern]

According to a report from Steve Adams of MLB Trade Rumors, the Blue Jays have agreed to a two-year minor league contract with right-hander Josh Winckowski. He was cut by the Red Sox earlier this offseason.

Winckowski, 27, will now return to the organization that selected him in the 2016 draft. He played the first four seasons of his professional career in the Blue Jays' system before he was traded to the Mets and Red Sox in quick succession during the 2020-21 offseason. The righty would go on to make his MLB debut for Boston in 2022. Since then, he has thrown 242.1 big league innings, all for the Red Sox, pitching to a 4.20 ERA and 4.36 xERA.

After spending much of the 2025 season on the injured list with elbow inflammation, Winckowski underwent an internal brace procedure in December (per Adams). That will keep him out for most of 2026, which explains the two-year minor league contract, but Adams notes that Winckowski hopes to return before the end of the season. 

Adams also mentions that the Blue Jays are planning to stretch Winckowski back out as a starter. He started 14 games as a rookie in 2022 but has primarily worked as a reliever since. However, he did start three games at Triple-A in 2025 and a handful of games at both the Triple-A and MLB levels the year before.

Winckowski was the second pitcher the Blue Jays inked to a two-year minor league contract on New Year's Eve. Earlier in the day, they came to terms on a similar deal with fellow right-hander Nic Enright.

Featured image courtesy of Nathan Ray Seebeck, Imagn Images.

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[Pendleton]

3 hours ago, Leo Morgenstern said:

According to a report from Steve Adams of MLB Trade Rumors, the Blue Jays have agreed to a two-year minor league contract with right-hander Josh Winckowski. He was cut by the Red Sox earlier this offseason.

Winckowski, 27, will now return to the organization that selected him in the 2016 draft. He played the first four seasons of his professional career in the Blue Jays' system before he was traded to the Mets and Red Sox in quick succession during the 2020-21 offseason. The righty would go on to make his MLB debut for Boston in 2022. Since then, he has thrown 242.1 big league innings, all for the Red Sox, pitching to a 4.20 ERA and 4.36 xERA.

After spending much of the 2025 season on the injured list with elbow inflammation, Winckowski underwent an internal brace procedure in December (per Adams). That will keep him out for most of 2026, which explains the two-year minor league contract, but Adams notes that Winckowski hopes to return before the end of the season. 

Adams also mentions that the Blue Jays are planning to stretch Winckowski back out as a starter. He started 14 games as a rookie in 2022 but has primarily worked as a reliever since. However, he did start three games at Triple-A in 2025 and a handful of games at both the Triple-A and MLB levels the year before.

Winckowski was the second pitcher the Blue Jays inked to a two-year minor league contract on New Year's Eve. Earlier in the day, they came to terms on a similar deal with fellow right-hander Nic Enright.

Featured image courtesy of Nathan Ray Seebeck, Imagn Images.

 

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Wincky is Blue Jays message board royalty, this is a true homecoming 

[jaysblue]

Nice pickup! Definitely might be available at the end of the season and can be a BP piece or swing starter in 2027. 

[John_Havok]

3 hours ago, Pendleton said:

Wincky is Blue Jays message board royalty, this is a true homecoming 

The one and only player interview we got on our old Breaking Blue podcast.

Legend

[Spanky__99]

6 hours ago, Pendleton said:

Wincky is Blue Jays message board royalty, this is a true homecoming 

He was interviewed by the fellas on here, right. Cool beans!

[Nexii]

Anyone have a link to the interview? Sounds interesting

[Spanky__99]

24 minutes ago, Nexii said:

Anyone have a link to the interview? Sounds interesting

 

 

[G-Snarls]

Love signings like this 

No real risk. Potential nice reward with some patience. 

[Jays24]