Add one final transaction to the list before the calendar flips to 2026.
According to MLB Trade Rumors’ Steve Adams, the Toronto Blue Jays agreed to a two-year, minor-league deal with injured right-hander Josh Winckowski on Wednesday, reuniting the 27-year-old with the organization that drafted him in the 15th round nearly 10 years ago.
Winckowski, who was non-tendered by the Boston Red Sox prior to last month’s deadline, only pitched 11.2 innings last season due to a right flexor strain and had a brace inserted in his elbow earlier this month to repair the injury. He’ll likely miss most, if not all, of the 2026 season but hopes to resume pitching off a mound before the end of the year.
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
Once healthy, the Blue Jays plan to stretch Winckowski — who last pitched on May 11 at triple-A — out as a starter, per Adams’ report. Most of his major league career has been spent as a multi-inning reliever, except for his rookie campaign in 2022, when all but one of his 15 appearances were as a starting pitcher. But he’s also routinely made starts at triple-A over the years.
Winckowski, of course, came up as a starter in the Blue Jays organization. But he was packaged along with fellow prospects Yennsy Díaz and Sean Reid-Foley in the 2021 Steven Matz trade with the New York Mets. He was then flipped to the Boston Red Sox less than a month later as part of a three-team deal that also included the Kansas City Royals.
The 6-foot-4, 215-pound righty enjoyed a career year with the Red Sox’s bullpen in 2023, pitching to an impressive 2.88 ERA and 3.91 FIP over 60 appearances (84.1 innings), recording a 13.9 per cent strikeout-minus-walk rate. He features five pitches, headlined by his mid-90s sinker, which is accompanied by a four-seamer, cutter, slider and changeup.
Winckowski will feature an additional year of club control in 2028 if he remains on the Blue Jays’ 40-man roster through the ’27 season.