Ex-Cubs Pitcher Finds New Home With Division Rival
The Chicago Cubs have seen a familiar name move on to another organization, as veteran left-handed pitcher Josh Fleming has reportedly agreed to a minor-league deal with the St. Louis Cardinals. The move keeps Fleming in the National League Central and places him with one of Chicago’s most familiar division rivals.
Fleming’s move to St. Louis comes only days after his time with the Cubs came to an end. Chicago released the left-hander on Aug. 17, and he did not have to wait long before finding another opportunity. According to a report from the St. Louis Post-Dispatch, the Cardinals signed Fleming to a minor-league contract and plan to send him to Triple-A Memphis.
For Fleming, the agreement represents another chance to work his way back toward the Major Leagues. The 30-year-old pitcher has already experienced several different stops during his professional career, including time with the Tampa Bay Rays, Philadelphia Phillies, Toronto Blue Jays and Cubs. His ability to work as both a starter and a bulk reliever gives him some versatility that can be valuable to an organization dealing with pitching needs.
Fleming joined the Cubs organization on July 8 after being released by the Toronto Blue Jays. His opportunity with Chicago came at a time when the Cubs were dealing with several pitching injuries and needed additional depth throughout their system. Although he did not ultimately establish himself on Chicago’s Major League roster, he provided useful innings at Triple-A Iowa.
With Iowa, Fleming made five appearances and worked 18.1 innings. He posted a 3.44 ERA, struck out 13 hitters and walked only four. Those numbers suggested that he was capable of providing reliable depth, even though the Cubs ultimately decided that they had better options available as the season progressed.
The Cardinals now have an opportunity to see whether Fleming can turn that minor-league performance into another Major League opportunity. St. Louis is familiar with the challenge of building pitching depth during a long season, and a veteran who can handle multiple roles can become especially useful when injuries or workload concerns affect the pitching staff.
The move is also interesting because of the rivalry involved. The Cardinals and Cubs are two of the most recognizable franchises in the National League Central, and their games routinely carry additional importance because of the history between the organizations. Fleming’s arrival in St. Louis does not immediately create a major threat to Chicago because he is beginning with the Cardinals’ Triple-A affiliate, but his experience could eventually put him in position to face his former organization.
There is one important detail, however: the Cubs and Cardinals have already completed their regular-season meetings for 2026. According to the report, the two teams finished their season series on Aug. 16. Therefore, Fleming would not face his former team during the regular season unless the Cardinals and Cubs eventually meet in the postseason.
That possibility adds an intriguing layer to the move. If Fleming reaches the Cardinals’ Major League roster and St. Louis makes a postseason run, the former Cub could potentially find himself on the opposite side of a playoff matchup. While that scenario remains uncertain, it illustrates how quickly circumstances can change for veteran players during the final stages of an MLB season.
Fleming’s professional background gives St. Louis another reason to take a look at him. During his Major League career, he has appeared in 81 games, including 25 starts, and has accumulated 257.2 innings with a 4.88 career ERA. Those numbers do not necessarily make him a frontline starter, but they demonstrate that he has considerable experience handling Major League hitters.
His most successful period came earlier in his career with Tampa Bay, where he demonstrated the ability to fill different roles depending on the team’s needs. That flexibility could be his biggest selling point with the Cardinals. Rather than expecting Fleming to immediately become a major piece of their rotation, St. Louis can use him as organizational depth while evaluating whether he deserves another opportunity in the majors.
For the Cubs, the decision to release Fleming appears to have been largely about roster management. Chicago has been dealing with pitching injuries, but the organization also strengthened its staff around the trade deadline and has remained in contention. The Cubs have therefore had to make difficult decisions about which pitchers remain part of the organization’s plans.
Fleming’s departure does not mean that Chicago has suddenly lost a key member of its pitching staff. Instead, it represents another example of how competitive the roster environment can become as teams approach the postseason. Fleming pitched reasonably well in Iowa, but the Cubs ultimately determined that there was no clear path for him to reach their Major League roster.
For Fleming, joining St. Louis may actually provide a better opportunity. Starting with Memphis gives him a chance to continue pitching regularly while remaining close to a Major League call-up. If the Cardinals encounter injuries or need additional left-handed depth, Fleming could quickly become a candidate for promotion.
The timing also makes the move particularly significant. With the regular season entering its final stretch, every opportunity becomes more important for veteran players trying to remain in the Major League picture. Fleming now has a chance to finish the season strongly and potentially position himself for another opportunity in 2027.
Ultimately, Fleming’s move from the Cubs to the Cardinals is a relatively small transaction, but it carries several interesting storylines. A former Cub is joining Chicago’s division rival, a veteran pitcher is receiving another opportunity to continue his career, and St. Louis is adding experienced pitching depth at an important point in the season.
The immediate assignment to Triple-A Memphis means Fleming will have to earn his way back to the majors. However, his previous experience, versatility and respectable numbers with Iowa give him a foundation to build on. If he can continue pitching effectively, the Cardinals could eventually view him as more than just minor-league depth.
For now, Fleming’s next chapter begins in St. Louis. Whether that chapter eventually brings him back to the Major Leagues remains to be seen, but the former Cubs pitcher has secured another opportunity—and with a division rival, no less. In a sport where pitching depth can disappear quickly because of injuries and workload, that opportunity could prove valuable for both Fleming and the Cardinals.
