The MLB Trade Deadline is now a little over four weeks away, and the Chicago Cubs should be one of the more aggressive teams to acquire the talent to push them over the edge. The Cubs’ most pressing need is a starting pitcher, but they have also indicated they could add a bat.
The Cubs have inquired about the Miami Marlins’ top two arms, Sandy Alcántara and Edward Cabrera, who, if they could add one or both, would bolster the starting rotation. The bullpen started the season off shaky, but has been one of the better aspects of the team as of late, with Daniel Palencia, Porter Hodge, and Ryan Pressly looking like solid late-inning options out of the pen.
With the Cubs already inquiring about arms and getting things in motion to outbid other teams, one ex-MLB executive thinks the Cubs will win the Trade Deadline in the National League Central.
Former MLB executive believes the Cubs will win the Trade Deadline in the NL Central
President of Baseball Operations Jed Hoyer and general manager Carter Hawkins’ contracts expire after this season, and they need a great Trade Deadline to get them into the postseason and to justify renewing their contracts. There could potentially be more sellers at the deadline as more teams drop out of contention, giving Hoyer and Hawkins options to get the deal they want.
Former MLB executive Jim Bowden, who was the Senior VP and general manager of the Cincinnati Reds and Washington Nationals, said on a recent appearance on the popular baseball YouTube show, Foul Territory, that he thinks the Cubs will win the Trade Deadline for the Central, with his sources in the industry, saying Hoyer and Hawkins are “all-in.” Bowden also adds that the Cubs are willing to part with top outfield prospect Owen Caissie to get a deal done.
“The Cubs are going to win the trade deadline in the NL Central, says @JimBowdenGM.
“As I talk to people in the industry, they’re all-in.”
The Cubs are going to win the trade deadline in the NL Central, says @JimBowdenGM. 👀
"As I talk to people in the industry, they're all-in." pic.twitter.com/h7cfaGTWJw
— Foul Territory (@FoulTerritoryTV) June 30, 2025
The Cubs need to go all-in if they’re to have a shot at winning
The Cubs have not made the playoffs for five seasons, with 2020 being the last season they made it, and 2017 being the last time they won a playoff game. Acquiring Kyle Tucker in the offseason was the first indication that the Cubs were making this season about getting into the playoffs, and adding another big name to better the roster should help get the fan base more excited than they are.
If the Cubs want to have any hope of re-signing Tucker past this season, they need to show Tucker they’re willing to go all-in to win it all.
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