
The Toronto Blue Jays signed a pitcher away from a division rival in an under-the-radar move.
Toronto signed former Boston Red Sox pitcher Josh Winckowski to a two-year minor-league deal. The move didn’t get much buzz due to Winckowski being out for most of 2026 after he underwent Tommy John surgery.
Despite missing most of 2026, Toronto took a flier on the right-handed pitcher to add some depth in 2027. And on Tuesday, the Dunedin Blue Jays – Toronto’s Single-A team – announced that Winckowski has begun his rehab assignment.
“Back where it started! Josh Winckowski has been assigned to Dunedin on MiLB rehab and will start tonight!,” the Dunedin Blue Jays wrote on X.
In his rehab outing, Winckowski went 1.2 innings, allowing 1 run on 2 hits while striking out 1. It’s a positive first step for the 6-foot-4 right-hander as he could be a key part of the Blue Jays pitching staff next season.
Toronto selected Winckowski in the 15th round of the 2016 MLB Draft, and in 2021, he was part of a trade package for Steven Matz. Just a month later, the New York Mets dealt him to the Red Sox, where he went on to make his MLB debut in 2022.
Winckowski has pitched in parts of four MLB seasons, going 13-14 with a 4.20 ERA in 121 games, including 21 starts.
Toronto Blue Jays Plan to Use Winckowski as a Starter
After Boston DFA’d Winckowski and he elected free agency, he opted to sign a two-year deal with Toronto.
Although the first year was more about rehabbing and getting back into the game at the end of the season, Toronto plans to build him up as a starter, according to MLBTradeRumors’ Steve Adams.
“Source: Right-hander Josh Winckowski is signing a two-year minor league deal with the Blue Jays. 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,” Adams wrote on X.
Winckowski has begun his rehab assignment, and perhaps he could return to the MLB in September as a reliever if he can build up enough. But for now, the focus is on 2027 and being a potential starter option for Toronto.
Toronto Right Now

GettyBlue Jays battling for playoff spot.
The Blue Jays are battling for a playoff spot but lost to the Kansas City Royals in the series opener on Tuesday.
Toronto played poorly, and some costly mistakes ended up being the difference in the loss, which was frustrating for the Blue Jays.
“It’s a game that wasn’t clean after an off day,” said Blue Jays manager John Schneider. “Those games happen. Unfortunately, it happened tonight, but usually that’s not how we play.”
Despite the loss, Max Scherzer and Toronto have to turn the page and have one simple focus: Win.
“Play well,” responded Scherzer. “Everybody’s got to play well. That’s how you win ball games at the big-league level. Gotta pitch, gotta hit, gotta play defence, bullpen, bench guys, you name it. Everybody’s gotta play well.”
The Blue Jays are 64-69 and 3 games back of a Wild Card spot.
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