Blue Jays add former Red Sox pitcher recovering from injury amid Bo Bichette, Kyle Tucker chase

The Toronto Blue Jays have added another arm to their pitching staff, though this latest addition is unlikely to see game action in 2026. The move underscores the team’s ongoing roster reshaping as it reportedly pursues key players like Bo Bichette and Kyle Tucker.

Josh Winckowski, 27, spent the majority of his career with the Boston Red Sox, but missed significant time this year due to an elbow strain that required surgery earlier this month. His new agreement with the Blue Jays was reported by Steve Adams of MLB Trade Rumors, though the team has yet to announce it.

“Source: Right-hander Josh Winckowski is signing a two-year minor league deal with the #BlueJays. 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.

Winckowski’s career path and background

Winckowski’s connection to the Blue Jays dates back to 2016, when Toronto originally drafted him out of high school. After a series of trades, he eventually landed with Boston, where he made his major league debut in 2022 as a starter. That season, he posted a 5-7 record with a 5.89 ERA and 44 strikeouts over 70 innings.

Josh Winckowski #25 with the Red Sox pitches the ball. Abigail Dean/Getty Images

In 2023, he transitioned effectively to the bullpen, emerging as one of the Red Sox’s most reliable relievers. He appeared in 60 games, recording a 2.88 ERA and 82 strikeouts across 88 innings. Despite a promising start to 2025, his season ended prematurely due to the elbow injury that now requires rehabilitation.

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Outlook with the Blue Jays

The two-year minor league deal gives Winckowski the time to properly recover without immediate pressure to contribute at the big-league level. The move also reunites him with the franchise that first drafted him, offering a fresh start with a club focused on strengthening its roster for both the present and future.

The Blue Jays’ front office will likely monitor his recovery closely while continuing their aggressive offseason pursuits, including efforts to retain Bichette and potentially add impact players like Tucker.