The St. Louis Cardinals find themselves in a tricky situation. While the front office appears to be heading toward a rebuild — especially with leadership changes on the horizon — the team is still managing to win. This makes the trade deadline a tough balancing act. If they choose to buy and then miss the playoffs, it could feel like a wasted effort. But if they sell while the team is playing well, it could upset fans.

Bleacher Report’s Zachary Rymer recently confirmed the surprising trade that Cardinals will be trading All-Star utility player Brendan Donovan. Rymer admitted it unlikely, but still possible. He pointed out that Donovan has come up in trade rumors before, and with his value potentially at its peak, now might be the right time to explore a deal — especially with a front office transition set for after the 2025 season, when Chaim Bloom will take over from John Mozeliak.

If the Cardinals start slipping in the playoff race, Rymer suggests it could be smart to get ahead of a rebuild. The team’s farm system isn’t particularly strong, and moving Donovan could help bolster it. Though a trade would be a major surprise, the Cardinals might listen if another team is willing to overpay for Donovan. His current level of play likely represents his peak, meaning his trade value may only drop going forward. While holding onto him remains the most probable outcome, the unpredictable nature of the trade deadline means anything is possible.