The Chicago Cubs have been showing signs of being something special this season.
As of this writing, the team sits atop the NL Central Division, with a comfortable-ish 5-game lead over the second place St. Louis Cardinals.
Their versatile and potent offense has been elite-tier throughout the year, consistently ranking high in runs, batting average, stolen bases, and run differential.
Their bullpen, once though to be the team’s biggest weakness, has turned around nicely and currently ranks among the best in baseball. Since May 14, it has posted a ridiculously tight 0.82 ERA.
The starting rotation needs a big-time addition or two, but it has held together relatively well considering that the Cubs have lost 60% of their projected front 5 (Justin Steele, Shota Imanaga, and Javier Assad) for either most or all of the season thus far.
The Time To Win Is Now (And Maybe Next Year)
It would appear that the time is now to win. And that would mean going out and making some trades before the July 31st deadline to make that happen.
Digging deeper into the realities of this roster, though, it would appear that this Cubs team, as it stands now, really has just a two-year window to make something big happen.
And why is that?
The contract status of key members of this squad may indicate that a major turnover is on the precipice of happening by the end of the 2026 season.
Ian Happ, Nico Hoerner, and Jameson Taillon will flat-out become free agents after 2026. Matthew Boyd, Carson Kelly, Shota Imanaga, and Colin Rea have options (either team or player) complicating their Cubs contract status. Seiya Suzuki, meanwhile, is eligible for arbitration after 2026, with free agency looming for the 2028 season.
The Chicago Cubs And The Great Purge
This means that Cubs ownership will have a lot of big contracts up at roughly the same time, with each likely to demand a sizable pay increase for the players. The last time that happened, we saw the great purge of 2021, with the Cubs trading away key World Series figures Anthony Rizzo, Kris Bryant, and Javier Baez near the trade deadline, as well as Craig Kimbrel, Joc Pederson, and Andrew Chafin. The purge was preceded that offseason, in late 2020, by the team non-tendering Kyle Schwarber and trading Yu Darvish.
The mass of players moved this time around wouldn’t be as great, but it would signify a major chemistry and makeup-rattling roster upheaval that would definitely change the outlook of the team.
To make matters more complicated, at least a few of their talented top prospects at Triple-A, pegged to possibly replace some of the outgoing veterans, will be gone this season if the team is serious about making aggressive trade moves in anticipation of a deep playoff run.
So, with veterans likely to move on and fewer assets available to move up from the minors to replace them, it’s pretty clear that there will be a two-year window for this team, as it exists right now, to make something big happen.
…And Then There’s Kyle Tucker (and PCA)
Apr 15, 2025; San Diego, California, USA; Chicago Cubs right fielder Kyle Tucker (30) hits a single during the fifth inning against the San Diego Padres at Petco Park. Mandatory Credit: Denis Poroy-Imagn Images
And, even then, there’s the huge detail of Kyle Tucker and his looming free agency.
Losing Tucker would create a massive hole to fill and, possibly, alter the trajectory of the team. With rumored expectations of a 10-year deal worth in the neighborhood of $500 million, it might appear to be more likely that Tucker will be an ex-Cub in 2026.
The long-term health of the major league club would be helped immensely by ownership doing whatever it takes to keep Tucker and, while they’re at it, extending Pete Crow-Armstrong through the reasonable rest of his career.
In the meantime, Chicago has to assume a “win now” attitude given the business realities facing them.
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