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Chicago Cubs: Kyle Tucker extension questioned in wake of trade deadline cold feet
MLB: Cleveland Guardians at Chicago Cubs Cubs president of baseball operations Jed Hoyer speaks before a baseball game between the Chicago Cubs and the Cleveland Guardians at Wrigley Field. Mandatory Credit: Kamil Krzaczynski-Imagn Images

The Chicago Cubs disappointed a lot of fans by not acquiring a high-end starter and high-leverage reliever– their two biggest needs– by the July 31 trade deadline.

Coming off that letdown, there has to be real doubt, at least in the fans’ eyes, regarding the team’s willingness to go “all-in” when it comes to extending multi-tool right fielder Kyle Tucker.

The 28-year-old four-time All-Star was acquired in a 3-for-1 trade this offseason from the Houston Astros in what was deemed a high-risk, high-reward deal that included Chicago sending off their no. 1 draft pick Cam Smith, third baseman Isaac Paredes, and pitcher Hayden Wesneski for Tucker, who would be eligible for free agency at the end of the 2025 season.

It was a shocking move from the usually conservative Cubs front office and one which teased, perhaps, a new mindset within the organization.

Chicago Cubs went back to playing it safe at the trade deadline

That aggressive mindset has to be seen as a one-and-done proposition, however, in the wake of their unwillingness to pull the trigger on a major trade this past Thursday.

Especially frustrating is the fact that the Cubs’ big gamble with Tucker has paid off, with the lefty becoming a linchpin for a stellar and versatile offense that has helped motor the team to the second best record in baseball. They got this far, riding on the moves they made, but then backed out as they needed just a bit more to ensure they got to the next level.

Some have tied the team’s deadline cold feet to Cubs president of baseball operations Jed Hoyer’s recent multi-year contract extension.

Hoyer’s change of heart?


MLB: Chicago Cubs Press Conference Chicago Cubs president of baseball operations Jed Hoyer talks to the media after introducing pitcher Shota Imanaga (not pictured) during a press conference at Loews Chicago Hotel. Mandatory Credit: Kamil Krzaczynski-Imagn Images

Did Hoyer have extreme hunger to make this team a winner in the offseason, with his job potentially on the line, and then adopted a “let’s hold back and play it safe” mindset with his job secured?

Many think that was the case and, by extension, believe that this bodes poorly for the Cubs’ chances of signing Tucker, in competition with aggressive, free-spending teams like the Yankees, Dodgers, Phillies, and Red Sox.

Was not trading away their top prospect, right fielder Owen Caissie, a sign that Hoyer and company are already working under the assumption that Tucker will be gone?

Sam Olbur of the Locked on Cubs podcast voiced this concern in a post-deadline rant:

“Is Tucker gone? I mean, are they just moving on? And so hey, we’re playing the long haul now that Jed got an extension. ‘Hey, I know I’m not resigning Tucker. So, I got to hold on to [Owen] Caissie. I know I’m not re-signing Tucker. And now that I’m going to be here for the next five years, I can’t lose that type of prospect. I already lost one in Cam Smith. I can’t lose Smith and Caissie if I know I’m not signing Tucker.’”

Moving on from Kyle Tucker?


MLB: San Diego Padres at Chicago Cubs Apr 4, 2025; Chicago, Illinois, USA; Chicago Cubs outfielder Kyle Tucker (30) is greeted by manager Craig Counsell (11) after scoring against the San Diego Padres during the fifth inning at Wrigley Field. Mandatory Credit: David Banks-Imagn Images

In a pre-trade deadline piece for The Athletic, Patrick Mooney and Sahadev Sharma talked up the reality that the Cubs may have been going into July 31, working under the assumption that Tucker might not be back:

“The perception is the Cubs are unwilling to trade Owen Caissie for a rental player, but they would consider moving their top prospect in the right deal…The Cubs are cognizant of a future that may not include Kyle Tucker, who’s positioned to be next winter’s No. 1 free agent.”

In an interview after the deadline, Hoyer talked up the possibility of having both Caissie and Tucker in the outfield. That would, indeed, be a best of both worlds proposition, although the Cubs would finally have to address the idea of moving on from Ian Happ.

But fans have been burned before, sold on the Cubs’ big, bold plans, only to see the team work conservatively, in half-measures, seemingly more concerned about value for their money than actually winning.

This article first appeared on ChiCitySports and was syndicated with permission.

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