Toronto Blue Jays Make Strategic Moves for Future Seasons

The Toronto Blue Jays have been busy during the off-season, making strategic moves to bolster their pitching depth as they look ahead to 2027. On New Year’s Eve, the team signed two pitchers, Nic Enright and Josh Winckowski, to minor league deals. These signings are part of a long-term strategy aimed at strengthening the organization’s pitching staff in the coming years.

The 2027 Addition: Nic Enright

Nic Enright made his Major League Baseball debut with the Cleveland Guardians in the 2025 season. He appeared in 27 games, posting a record of 2-1 with a 2.03 ERA and a 1.161 WHIP. Enright also recorded one save on August 4 against the New York Mets. However, his season came to an abrupt end on September 2 when he was placed on the 15-day injured list due to right elbow and forearm inflammation. This led to Tommy John surgery in October, which will keep him out of action until late 2026.

Enright, who is 28 years old, was designated for assignment by the Guardians on November 18. He will spend the entire 2026 season rehabbing from the surgery and is expected to be ready for spring training in February 2027.

In addition to his baseball career, Enright has faced significant health challenges. On December 22, 2022, he was diagnosed with Stage 2 Hodgkin’s lymphoma. Since then, he has undergone immunotherapy treatment after each season.

During the 2025 season, Enright worked exclusively out of the bullpen for the Guardians. His longest outing was two innings, and his highest pitch count in a single game was 36.

An Addition Toward the End of 2026: Josh Winckowski

Josh Winckowski, a former Blue Jays minor leaguer, was traded in 2021 to the New York Mets as part of a deal that included Yennsy Díaz and Sean Reid-Foley in exchange for left-hander Steven Matz. Before making his major league debut, he was traded again to the Boston Red Sox.

Winckowski has appeared in 121 games for the Red Sox, compiling a 13-14 record with a 4.20 ERA and a 1.465 WHIP. He has been used both as a starter and a reliever. In the 2025 season, he appeared in six games, going 0-1 with a 3.86 ERA and a 1.371 WHIP. His final appearance of the season came in April, and in May, he was placed on the injured list with right elbow inflammation.

This injury eventually required internal brace surgery, which will keep him out of action until late into the 2026 season. Once fully recovered, Winckowski could provide the Blue Jays with flexibility as both a starter and a reliever.

Winckowski’s best season came in 2023, when he pitched in 60 games for Boston. Over 84 1/3 innings, he went 4-4 with a 2.88 ERA and a 1.423 WHIP.

What Do These Two Signings Mean?

Both Enright and Winckowski are not expected to contribute to the Blue Jays’ 2026 season. Instead, these moves are focused on the 2027 season. After the 2026 season, several key pitchers on the Blue Jays’ roster will become free agents or have opt-out clauses. This includes Kevin Gausman, Shane Bieber, Eric Lauer, and Yimi García, as well as José Berríos.

The Blue Jays currently have high-leverage arms like Jeff Hoffman, Trevor Rogers, and Louis Varland in the bullpen. However, there are many uncertainties beyond that. Health is always a concern in baseball, and having more pitching depth can make a significant difference.

By signing Enright and Winckowski, the Blue Jays are adding valuable depth to their pitching staff for the 2027 season. These moves reflect a forward-thinking approach to building a competitive roster in the coming years.