According to reports, the Toronto Blue Jays closed out 2025 with a little business before the calendar flipped to 2026, with a look towards the end of 2026 and 2027. The Blue Jays added pitchers Nic Enright and Josh Winckowski to minor league deals on New Year’s Eve. Both of these players signed two-year deals as they recover from arm surgeries. ESPN’s Alden Gonzalez broke the Enright deal, while Steve Adams of MLB Trade Rumors reported the Winckowski signing.
Blue Jays Sign Pitchers Enright, Winckowski to Ring in New Year
The 2027 Addition
Enright made his Major League Baseball debut in the 2025 season with the Cleveland Guardians, appearing in 27 games with a record of 2-1, a 2.03 ERA, and 1.161 WHIP, while also picking up one save on Aug. 4 against the New York Mets.
The 28-year-old made his last appearance on Sept. 2, before being placed on the 15-day injured list with right elbow and forearm inflammation. This would end the right-hander’s season, eventually needing to undergo Tommy John surgery in October.
The Guardians designated Enright for assignment on Nov. 18, and he is set to spend the duration of the 2026 season rehabbing from the procedure. Enright should be ready to be a full participant in spring training when camp opens in February 2027.
Source: The Blue Jays have agreed to a 2-year minor league deal with RH Nic Enright.
Enright, 28, beat Hodgkin lymphoma and had a really nice year with the Guardians in 2025, with a 2.03 ERA in 31 innings.
He’ll spend 2026 rehabbing Tommy John and look to bounce back in 2027.
— Alden González (@Alden_Gonzalez) December 31, 2025
https://platform.twitter.com/widgets.js
On Dec. 22, 2022, Enright was diagnosed with Stage 2 Hodgkin’s lymphoma. Upon completion of each season, he has been undergoing immunotherapy treatment in each of the past three offseasons.
Enright worked solely out of the bullpen for the Guardians in 2025, with his longest outing being two innings, and his highest number of pitches in a single outing was 36.
An Addition Toward the End of 2026
A former Blue Jays minor leaguer, Winckowski was traded in 2021 alongside Yennsy Díaz and Sean Reid-Foley to the New York Mets for left-hander Steven Matz. Before he could debut in the majors, he was traded to the Boston Red Sox. With Boston, the right-hander has appeared in 121 games, pitching to a 13-14 record, 4.20 ERA, and 1.465 WHIP, being used as both a starter and a reliever.
Last season, the 27-year-old appeared in six games, going 0-1 with a 3.86 ERA and 1.371 WHIP. Winckowski’s final appearance of 2025 came in April. In May, with Worcester, the Red Sox’s Triple-A affiliate, Winckowski was placed on the injured list with right elbow inflammation.
Source: Right-hander Josh Winckowski is signing a two-year minor league deal with the #BlueJays. Had internal brace surgery earlier this month. Hoping to pitch late in 2026. Plan right now is to build him back up as a starter when he’s healthy.
— Steve Adams (@Adams_Steve) December 31, 2025
https://platform.twitter.com/widgets.js
The injury eventually led to an internal brace surgery that will keep him off the mound until late into the 2026 season. Winckowski gives the Blue Jays an option as both a starter and a reliever once he returns to full health.
Winckowski’s best season came in 2023, when he pitched in 60 games for Boston. Over 84 1/3 innings, Winckowski went 4-4 with a 2.88 ERA and 1.423 WHIP.
What Do These Two Signings Mean?
Enright is not going to pitch for the Blue Jays this season, and Winckowski will only be an option later in the season. So these are moves setting them up for 2027. After the 2026 season, Kevin Gausman, Shane Bieber, Eric Lauer, and Yimi García are all free agents, and José Berríos has an opt-out clause.
This leaves the Blue Jays with openings on the pitching staff that will need to be filled. Jeff Hoffman, Trevor Rogers, and Louis Varland will be high-leverage arms in the bullpen, but after that, there are many unknowns.
In baseball, health is never guaranteed, and you can never have too much pitching depth. These moves will give the Blue Jays much added depth for the 2027 season.
Main Photo Credit: Eric Canha-Imagn Images