The Toronto Blue Jays didn’t make headlines with a blockbuster on Wednesday.
They did something far more intriguing.
Toronto agreed to a two-year minor league contract with former Boston Red Sox right-hander Josh Winckowski, a move that barely ripples the national news cycle at first glance. But buried inside the details is a decision that hints at long-term planning — and a willingness to think beyond the present.
According to MLBTradeRumors’ Steve Adams, the Blue Jays don’t view Winckowski as bullpen depth. They plan to build him back up as a starter once he recovers from internal brace surgery earlier this month. The expectation is that he could return to game action late in the 2026 season.
It’s a small deal.
It’s also a revealing one.
Winckowski is just 27 years old, but his career already feels like it belongs to two different eras. Drafted by the Blue Jays in the 15th round of the 2016 MLB Draft, he was once a developmental project in Toronto’s system before being traded to the New York Mets in January 2021. A month later, he was re-routed again — this time to the Boston Red Sox — as part of a three-team deal that eventually sent Andrew Benintendi to the Kansas City Royals.
Winckowski finally reached the majors in 2022, debuting with Boston as a starter. But the role didn’t last. Over the last three seasons, he has been used almost exclusively as a reliever, becoming a familiar middle-innings arm rather than a fixture in the rotation.
In 121 career MLB appearances, Winckowski has made just 21 starts, compiling a 13–14 record with a 4.20 ERA. He’s not a bat-misser — his 195 strikeouts in 242.1 innings reflect a pitcher who relies more on contact management than overpowering stuff. His best weapon is a heavy sinker, a pitch that generates ground balls but leaves little margin for error.
So why, after years in the bullpen and major surgery, would the Blue Jays see a starter again?
The answer lies less in what Winckowski has been — and more in what Toronto may soon lose.
Multi-year minor league deals are not unusual for pitchers expected to miss most of a season due to injury. They offer the player stability and give organizations the chance to invest in rehabilitation without the pressure of immediate results. It’s a model Toronto has seen work before.
Shane Bieber took a similar path with Cleveland in 2025, signing a multi-year deal while rehabbing, with a second-year option that ultimately kept him in Toronto for 2026. The Blue Jays believe in their pitching infrastructure — and they’re willing to bet on it again.
But the timing makes this deal stand out.
Both Bieber and Kevin Gausman are scheduled to become free agents after the 2026 season. That reality looms over every rotation decision the front office makes. Developing internal options now, even speculative ones, could soften the blow if one or both veterans depart.
Winckowski hasn’t been a full-time starter since 2022. Rebuilding his workload, durability, and pitch mix after surgery will be a long process. There are no guarantees he ever reaches a major league rotation again. Still, Toronto sees enough raw material — age, frame, sinker profile — to justify the experiment.
And he won’t be alone in that future picture.
Looking ahead to 2027, the Blue Jays expect to have arms like Dylan Cease, Trey Yesavage, and Cody Ponce in the mix, with JosĂ© BerrĂos remaining a possibility depending on his contract status. Top prospects Jake Bloss and Ricky Tiedemann could factor into the equation as well, assuming health and development cooperate.
In that crowded landscape, Winckowski represents a low-risk, long-horizon option — a pitcher who doesn’t need to be ready now, only right later.
Of course, rotation planning isn’t the only question Toronto must answer. The organization has also been linked to major position-player decisions involving Bo Bichette, Alex Bregman, and Kyle Tucker, each move carrying its own financial and competitive implications.
But while those conversations dominate headlines, the Winckowski signing reveals something quieter and perhaps more telling.
The Blue Jays are thinking past the next season.
Past the next contract.
Past the obvious solutions.
They’re betting that somewhere down the road — late 2026 or beyond — a pitcher once drafted by this organization, lost, rerouted, and reshaped, might return as something new.
It’s not a promise.
It’s a possibility.
And for a franchise staring at rotation uncertainty on the horizon, sometimes that’s exactly where the future begins.
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