Former MLB Executive Expects Cubs to Win Trade Deadline: 'They're All-In'

With the calendar finally shifting to July on Tuesday, focus also shifts for the Chicago Cubs and really every team in baseball to the trade deadline at the end of the month.

The Cubs are an interesting case as a team that very clearly has the makings of a potential contender in the National League with an offense that can match up with anyone on a good day.

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While the opportunity to win right now seems to be there in Chicago, there are weaknesses that need to be addressed if the Cubs are going to have any chance at overcoming what is an absolute gauntlet of a National League.

There may not be a team in baseball linked to more trade rumors than the Cubs, but according to one former executive, it's not for no reason.

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Chicago is being the most aggressive team in baseball right now in trying to make trades even four weeks before the deadline actually comes.

Former Major League general manager and current insider for the Athletic Jim Bowden appeared on an episode this week of Foul Territory and painted the picture very clearly that big moves are coming in the Windy City:

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

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"The Cubs are going to win the trade deadline in the NL Central," Bowden said while discussing the fact that the race is narrowing in the division. "They're everywhere right now, and they're willing to part with [top prospect] Owen Caissie as part of a package...Jed Hoyer and Carter Hawkins literally are everywhere. As I talk to people in the industry, they're all-in and they're gonna do what it takes to win."

Bowden went on to break down every team in the division and why he does not expect huge deadline moves from any of them.

Entering a new week and a series against the Cleveland Guardians, the Cubs cling to a two-game lead over the Milwaukee Brewers and three games over the St. Louis Cardinals.

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If they want to affirm their status as the top dog in the division and start to put a stranglehold on things down the stretch, outbidding the light spending teams they are competing against is the way to do it.

According to Bowden, though, fans in Chicago who want to see exactly that happen are going to get their wish over the coming weeks as the deadline approaches.

Keep an eye on a major blockbuster deal coming for the Cubs sooner rather than later.

For more Cubs news, head over to Cubs On SI.