The Toronto Blue Jays have wrapped up their 2025 free agency with a low-risk move that could pay dividends down the road.
Josh Winckowski signed a two-year minor league deal with Toronto, according to Steve Adams. The right-hander’s coming back to where it all started – the Blue Jays drafted him in the 15th round out of Estero High School in Florida back in 2015.
There’s a catch though. Winckowski had internal brace surgery earlier this month and won’t be ready to pitch until late 2026. When he’s healthy, the plan is to build him back up as a starter.
It’s been quite the journey for the 28-year-old since leaving Toronto’s system. He didn’t make his MLB debut until 2022 with the Boston Red Sox, where he’s spent parts of four seasons.
Winckowski’s logged 121 appearances at the big league level, including 21 starts, with a 4.20 career ERA. His best season came in 2023 when he posted a 2.88 ERA across 60 appearances for Boston.
This past season was limited – just six games with a 3.86 ERA before the injury issues cropped up.
What makes this interesting is the Blue Jays clearly have a plan. They’re not just taking a flyer on an injured pitcher – they know exactly what they’re getting and how long the timeline is.
The way I see it, this is smart asset management. Let Winckowski rehab with their trainers, get him healthy, and see if he can contribute when he’s ready. For a guy who’s shown he can pitch at the MLB level – he strikes out 7.2 batters per nine and keeps his walks manageable at 3.3 per nine – it’s worth the investment.
Plus there’s something to be said for coming full circle. Nearly a decade after the Blue Jays drafted him, Winckowski gets a chance to finally pitch for the organization that believed in him first.
All things considered, it’s the kind of move that won’t make headlines now but could look pretty smart if he comes back healthy and effective in 2026.
