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Blue Jays To Sign Josh Winckowski To Minor League Deal

By Charlie Wright | December 31, 2025 at 6:09pm CDT

Right-hander Josh Winckowski is joining the Blue Jays on a two-year minor league deal, per MLBTR’s Steve Adams. The 27-year-old recently had internal brace surgery and hopes to pitch late in the 2026 season, notes Adams.

Winckowski didn’t break camp with the Red Sox this past season, but was called up in early April. He made six appearances with the club before getting sent back down. The righty hit the IL in May with an elbow issue that ended up being a flexor strain. The injury ended his season. Winckowski was designated for assignment in mid-November. He elected minor league free agency shortly after.

The additional news that Winckowski underwent internal brace surgery this month sheds more light on his potential timeline. The procedure typically allows pitchers to return sooner than they would if they had Tommy John surgery. Winckowski will be building back up as a starter, adds Adams. With several months of recovery still ahead of him, it makes sense that the Blue Jays inked him to a two-year deal.

It’s a return home for Winckowski, who was drafted by Toronto out of high school in 2016. He delivered promising results in the lower levels of the minors, reaching High-A by 2019. Winckowski was then involved in a pair of notable trades ahead of the 2021 season. Toronto sent him to the Mets as part of a package for Steven Matz. Two weeks later, New York flipped him to the Red Sox in a three-team deal that involved Andrew Benintendi going to the Royals.

Winckowski debuted with Boston in 2022. He made 15 appearances (14 starts) for the big-league club, pitching to a 5.89 ERA. Winckowski struggled to miss bats (13.9% strikeout rate) but got ground balls at more than a 52% clip. The Red Sox transitioned Winckowski to a bullpen role in 2023, and the change paid immediate dividends. The righty’s fastball velocity jumped more than 2 mph, and his strikeout rate improved to 22.3%. Winckowski continued to get ground balls at a well-above-average rate. The combination of an improved arsenal and the persistent ability to keep the ball on the ground helped Winckowski post a sterling 2.88 ERA across 60 appearances. He finished with 19 holds as an important member of Boston’s bullpen.

The 2024 campaign was a step back for Winckowski, both in terms of stuff and production. His fastball and sinker velocities fell a bit, and he reverted to underwhelming strikeout numbers. Winckowski was demoted to Triple-A on two separate occasions. The injuries limited him to just 11 2/3 innings with the Red Sox this past season. His health, along with his pending arbitration and the fact that he was out of minor league options, likely contributed to him getting bumped off Boston’s roster. Winckowski will now head to Toronto with the hopes of recovering in time to help the major league squad.

Photo courtesy of Eric Canha, Imagn Images

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Toronto Blue Jays Transactions Josh Winckowski

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View Comments (16)
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16 Comments

  1. Canuckleball

    1 month ago

    The Jays are on a busted elbow binge right now!

    8
    Reply
    • Edp007

      1 month ago

      Well it is “elbows up” land in Canada now isn’t it ?

      7
      Reply
  2. bobbymac7

    1 month ago

    I’m liking these signings today. No harm, no foul and you might catch lightning in a bottle.

    4
    Reply
    • iains 2

      1 month ago

      Exactly, there is no such thing as a bad minor league signing. They have control of both players with no downside for two years. If neither pans out, the only thing lost is a minor league salary. They don’t eat a roster spot. If they work out, they include multiple years of control at the major league level.

      1
      Reply
  3. Butters

    1 month ago

    Looking at a few seasons he played they were very good, one not so good. Of course the injury limited him last season however I’m Surprised the Sox didn’t just do the same thing? Hope it works out.

    Reply
  4. DolemiteisMyname

    1 month ago

    @Bobby-I bet your all giddy with your Blue Jays making these power moves lol

    1
    Reply
    • bobbymac7

      1 month ago

      It hurts nothing to take a chance. Hoping for contributions in 2027.

      Reply
  5. Astros71

    1 month ago

    Blue Jays might need this down the stretch. You never know.

    2
    Reply
  6. drew ryce

    1 month ago

    You can win, Winckowski, you can win
    You can win, Winckowski, if you just brace up

    Reply
  7. BetterMuppet:JUDGEorKERMIT?

    1 month ago

    These 2 signings speak to the jays, walker, and all that but I would assume their rehab facilities in Dunedin certainly don’t hurt. I can’t imagine a better place to rehab than the jays facilities.

    2
    Reply
  8. playhard9

    1 month ago

    Cardinals could not get to him first?

    Reply
  9. Rsox

    1 month ago

    Good for Josh

    Reply
  10. Jacksson13

    1 month ago

    This gives the Blue Jays’ “Uniform Person” 6 weeks or so to figure out how to get “Winckowski” on the back of a uniform !!
    And the same amount of time for his teammates to figure out how to correctly pronounce “Winckowski”,

    Reply
    • Ignorant Son-of-a-b

      1 month ago

      “win-cow-skee”

      Reply
    • raregokus

      1 month ago

      It’s pronounced phonetically so as long as they’re smarter than you it should be no problem

      3
      Reply
  11. its_happening

    1 month ago

    Two low-key good signings by the Blue Jays.

    Reply

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