The Chicago Cubs pulled off one of the biggest moves of last MLB offseason when they acquired Kyle Tucker via a trade with the Houston Astros.
This deal was significant for several reasons. The first and most obvious one was that it showed the Cubs’ desire to be viewed as true contenders, given that Tucker is one of baseball’s premier sluggers.
But perhaps even more important than that in the eyes of fans was how it showed the willingness of Chicago’s front office to get creative when it comes to bolstering the roster.
It’s no secret that the Cubs have been notoriously averse to giving players big contracts in free agency. The largest contract they’ve given a player is still the eight-year, $184 million deal Jason Heyward got from the team in 2016. While this was a huge deal at the time, there are probably at least ten players who will get larger contracts in this current MLB offseason alone. And the Cubs probably won’t be one of the teams to sign a player on such a deal.
Chicago Cubs right fielder Jason Heyward | Charles LeClaire-Imagn Images
But making trades is a way for Chicago to still acquire top talent without breaking the bank, and getting Tucker was evidence of that. Therefore, the hope fans are clinging to this winter is that if Chicago isn’t going to sign a top free agent, then they can bolster the roster via trade just like they did one year ago.
MLB Insider Insider Keeps Cubs Out of Top 25 Trade Fits
On December 2, ESPN MLB insiders Jeff Passan and Kiley McDaniel published an article that listed the top 25 players who could potentially be traded this winter. In addition to this, he noted the percentage chance each player will be dealt, along with listing several teams that would make sense as trade fits.
The Chicago Cubs were not listed as a trade fit for any of the 25 players.
Free at ESPN: @kileymcd and I ranked the top 25 trade candidates this winter with their best potential fits and the likelihood they move. With the market percolating and the Winter Meetings starting Sunday, there will be deals. Get your foreknowledge here: https://t.co/mh8aX7nVLI
— Jeff Passan (@JeffPassan) December 2, 2025
The fact that Chicago was left off of this entire list raises many red flags. While it doesn’t guarantee that they will not be in play for these 25 players, Passan and McDaniel are typically viewed as among the two top insiders in the sport, and are almost always in “the know” about what’s happening behind the scenes regarding offseason activity.
Therefore, the Cubs’ omission in this article is likely indicative of what these insiders are hearing (or not hearing) about Chicago’s presence on the trade market.
And this is alarming, in the sense that it could mean the Cubs won’t trade for a top player, nor add one in free agency.
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