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Dylan Cease has always been viewed by Chicago Cubs fans as the one who got away, as the infamous 2017 trade with the Chicago White Sox is always remembered around this time of year. No need rehashing the details, as they have become embedded, but as the 2025 trade approaches, the Cubs may have a path toward a reunion with Cease.
In a surprising twist, Buster Olney of ESPN reports that the Padres have made Cease available, with the hope they can use the trade as a way to address other areas of need on their roster. In revealing that Cease is on the trade market, Olney adds that the Cubs have already had a conversation with the Padres about reuniting with their former top pitching prospect.
A surprise name has emerged in the starting pitcher market: Dylan Cease, who will be eligible for free agency at year's end. Perception of other teams is that the Padres are intent on making a push for the playoffs, and would use Cease to help fill other roster needs. Mets, AL…
— Buster Olney (@Buster_ESPN) July 23, 2025
Cubs fans have never given up hope that Cease may eventually return to the organization that drafted him, with rumors circling this past winter about a potential deal. Given the layers to the idea of the Padres trading Cease at the deadline, it may be difficult to find a scenario where he lands with the Cubs.
The first being that the Padres very much are in the National League postseason picture. Their preference likely is to trade Cease to an American League team; that way, they wouldn't have to worry about facing him during a potential World Series run.
Shocking Cubs trade rumor points to unexpected reunion in Chicago
The other is that the Padres are looking for pieces who can help them win this season. The Cubs really can't offer that without taking a significant loss when it comes to their Major League roster. Owen Caissie, in theory, could be someone who helps the Padres this season, but the Cubs won't be moving their top prospect for a pitcher who is a free agent after the season.
Cease, for his part, has been unlucky this season, sitting with an ERA of 4.64 despite having an expected mark of 3.46. Striking out over 30 percent of the hitters he has faced this season, it makes sense why the Cubs have, at least, checked in on him with the deadline approaching. However, it remains difficult to match the Padres and Cubs on a trade, given where each team stands this season.