The Toronto Blue Jays made a flurry of moves this past winter, but one transaction that went under the radar was the signing of right-hander Josh Winckowski. 

Winckowski, a former Blue Jays draft pick who was traded during the 2020/2021 offseason to the Mets in the Steven Matz deal, landed with the Boston Red Sox weeks later when he was moved again before the start of the regular season. He would make his debut for Boston in 2022 and has spent the past four seasons with the organization before landing with Toronto.

The Ohio product signed a two-year MiLB deal with the Jays this past winter, with the idea that he would be on the shelf for most (if not all) of the 2026 season while he rehabbed from Tommy John surgery. A right flexor strain sent him to the IL in May of 2025, and he missed the rest of the season because of it. This led to the internal brace procedure in December, which came a month after he was designated for assignment by the Red Sox and elected free agency.

Winckowski is an interesting option for the Jays in 2027, should there be a regular season.

The 28-year-old owns a career 4.20 ERA, a bulk of which stems from when the Red Sox were still trying to craft a starting pitcher out of the 6-foot-4 right-hander. He posted a 5.89 ERA and a 4.95 FIP as a rookie starter, making 14 appearances to the tune of 70.1 innings. He’s made a handful of starts since that rookie campaign, but since that season, Winckowski has become more of a bullpen arm.

As a reliever, Winckowski has posted a 3.80 ERA through 151.2 innings, posting a 1.490 WHIP while striking out 144 batters (8.5 K/9). He’s held opponents to a .277/.343/.401 slash line with a .744 OPS and a .338 BABIP. When he became a reliever in 2023, he pitched to a 2.88 ERA and a 3.91 FIP, pitching a career high 84.1 innings with three saves and an 8.8 K/9 (career-high).

The one drawback in Winckowski’s game is the contact, with the right-hander owning a career 9.9 H/9, which sat at the 9.5 H/9 mark during that impressive 2023 season. The Blue Jays’ defence could be a benefit to the former Sox hurler in an attempt to curb this stat, but it’s no secret that Winckowski is a groundball-heavy pitcher by trade.

Winckowski returned to the diamond late into the 2026 season in rehab stints and finished the year in Buffalo. Across six outings spread between Dunedin (three outings) and Buffalo, he allowed just one earned run (a home run) and eight hits across 13.2 innings, striking out 17 batters compared to five walks and a 0.95 WHIP.

Looking at the Blue Jays’ current bullpen picture heading into the offseason, there isn’t a ton of wiggle room.

Yimi Garcia, who spent most of the 2026 season on the IL, is a free agent, and so is Paul Sewald, a right-hander who joined the Jays via waivers in August. The Jays also have quite a few arms vying for a spot in the bullpen from an internal standpoint heading into next year, alongside Winckowski, including:

There are a few names that will be gearing more towards a starting role, such as Arrighetti, Francis, and Tiedemann (amongst others), which drops the names on this list by a few.

But the internal competition for spots outside of the pure ‘lock-in’ names, the return of players like Francis, Cody Ponce, Jake Bloss, and Jose Berrios from injury, plus any external additions the Jays make in free agency, will see quite a few names knocking for an opportunity on the big league stage next year. The names on this list could change over the winter due to various roster moves, but there still seems to be a strong list of contenders heading into spring training looking for similar opportunities.

Winckowski will be part of that list, but from an experience standpoint, he does have a leg up on most of the competition. If he can find that 2023 form, he would be a valuable bulk reliever for the Jays, which bodes well if the Jays decide to tinker with Spencer Miles as a starter next season.

There is also a chance that Winckowski is being geared towards starting under the Blue Jays, something MLB Trade Rumours writer Steve Adams advised was in the process when the club signed the former draft pick last winter. The trade for Arrighetti and returning names in Ponce, Francis, and Berrios, as well as potential external additions, could see this plan fizzle and Winckowski heads back to the bullpen, but that’s a problem the Jays can figure out come spring (or whenever players return to the diamond post CBA negotations).

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