​Left-handed pitcher Josh Fleming has spent much of the past several seasons bouncing between organizations in search of another extended opportunity at the majors. Once a dependable contributor for the Tampa Bay Rays, the 30-year-old now often serves as experienced depth for clubs in need of both starting and relief options. That role brought him to the Toronto Blue Jays on a minor league contract heading into the 2026 season, but his stay with Toronto proved unusually brief at the major league level. Just days after being released, Fleming had already found his way to another contender looking to bolster pitching depth.
Cubs are signing LHP Josh Fleming to a minor league deal, Marquee Sports Network’s Lance Brozdowski reported. Fleming spent last season with the Seattle Mariners and was released by the Blue Jays on Sunday. After four seasons with the Rays, followed by a stint with the Pittsburgh Pirates, Fleming returned to the big leagues with the Blue Jays to face the Dodgers in April, and he promptly yielded four earned runs in three innings. That start would prove to be the extent of his time pitching for Toronto at the major league level. After clearing waivers and continuing to work at Triple-A Buffalo, the Blue Jays released Fleming last week, freeing him to pursue opportunities elsewhere.
Although his Blue Jays contribution totaled only three innings, the veteran continued logging substantial innings in the minors while staying stretched out, and that seemed to appeal to a Chicago Cubs team dealing with notable pitching injuries this season. The Cubs evidently see value beyond Fleming’s brief major league stint this season and may view him as a potential starter within their own minor league system or as a depth option for the big league club down the stretch.
Fleming has been stretched out at Buffalo as well—12 of his 13 appearances there were starts—so whenever a need arises at Iowa or beyond, he can provide genuine length in both relief and spot starts, as Bleacher Nation’s Brett Taylor noted. On a minor league deal, he costs nothing in terms of a 40-man roster implication for now. That kind of flexibility could make Fleming an attractive choice if the Cubs require innings later this season. His experience as both a starter and reliever gives the organization another veteran arm capable of filling multiple roles without an immediate 40-man commitment.
While Toronto ultimately moved on after just one major league appearance, Fleming didn’t linger on the market for long. The Cubs appear convinced enough of his upside to give him another chance, hoping that his breadth of experience and versatility—coupled with the ability to deliver innings and length—will translate into dependable depth as they navigate a season marked by pitching injuries and shifting bullpen needs. If Fleming can recapture some of the form that once made him a reliable contributor, he could emerge as a meaningful piece for Chicago—whether as a starter in the minors who could be called upon for a spot start or as a multi-inning option out of the bullpen when called upon to rescue a stretched pitching staff.