3 steps the Cubs must take right now to avoid another depressing rebuild

Things have not been going well for the Chicago Cubs in recent weeks. The team's two ten-game win streaks from earlier this year feel like a distant memory, as the team has collapsed to the point where they've begun to flirt with .500 rather than a playoff spot. The league is starting to take notice of Chicago's struggles, and the Cubs have offered fans little reason for optimism as of late.

With the team struggling and a number of key players ticketed for free agency after this season, priority number one at this point for Jed Hoyer and the front office has to be avoiding a repeat of the team's disastrous 2021 season that kicked off a years-long rebuild and kept the Cubs out of the playoffs until just last year. Much of that work will have to wait until the offseason, but here's three things the Cubs should get to work on right away to avoid another rebuild.

Trading for a controllable starter

It was just a few short years ago, during the 2024 season, when the Cubs made a bold trade over the summer to land a valuable asset with multiple years of team control. Isaac Paredes was brought in to fortify the third base position both down the stretch that season and for the next several years even though the Cubs were more pretenders than contenders during that season.

The deal for Paredes itself was a mixed bag, with the All-Star third baseman struggling badly down the stretch with Chicago before being packaged alongside top prospect Cam Smith and right-hander Hayden Wesneski in the trade that brought Kyle Tucker to Chicago last year. Regardless of the outcome of that deal, however, the Cubs should look to replicate that process on the pitching side this year.

Whether the Cubs are in the race or not when the trade deadline rolls around later this summer, it's clear this rotation is in desperate need of a boost. Cade Horton is out for the year, Justin Steele's timeline for this year is riddled with uncertainty at this point, and players like Edward Cabrera and Shota Imanaga have not stepped up the way the Cubs were hoping.

Things will become even more dire this offseason, when Imanaga, Matthew Boyd, and Jameson Taillon are all due to reach free agency. That would leave the Cubs without much of any certainty in the rotation headed into 2026, and so adding a controllable arm to the rotation before this offseason's mass exodus takes place should be a top priority.

One strong candidate to be traded this summer is Twins right-hander Joe Ryan, who also saw his name come up in the rumor mill last summer. Ryan, who recently spoke about how he handles the endless trade speculation that surrounds him with Rob Bradford of the Baseball Isn't Boring podcast, has a 3.07 ERA and 2.93 FIP through 14 starts this year and is controlled through the end of the 2027 season.

Extending Ian Happ

Some Cubs fans have long dreamed of replacing stalwart left fielder Ian Happ with a star-level player, and for those fans Happ's impending free agency this offseason is a reason for celebration. The uncomfortable reality the Cubs must face, however, is that the team will find it virtually impossible to upgrade over its corner outfield duo of Happ and Seiya Suzuki in free agency this offseason.

A look at the 2026-27 free agent class underscores the point. A recent power ranking from MLB Trade Rumors of the ten best free agents available this winter places Happ #10 in this year's class among all free agents. The only outfielder ranked above Happ is Randy Arozarena of the Mariners. While Arozarena's 141 wRC+ this year is even better than Happ's 133, an unsustainable .367 BABIP and just six home runs make Arozarena a questionable fit for a Cubs team that needs more power.

To that end, an unusual 2026 season for the Cubs' left fielder has been just what the doctor ordered. Happ's 14 home runs so far have contributed to a .253 isolated slugging percentage on the year. That's his best figure since his rookie campaign back in 2017, and it's led to the best offensive season of Happ's career. The veteran's .232/.347/.485 slash line in 274 trips to the plate this year has been some of his best work in any season.

The one red flag in Happ's profile right now is a jump in strikeouts, but perhaps those concerns can help Happ and the Cubs agree on a shorter-term deal than he might otherwise seek in free agency. Happ already took one below-market extension with the Cubs a few years ago, and after recently notching the 1000th hit of his career remaining in Chicago and continuing to climb the organizational leaderboards surely holds some appeal for the veteran. If so, the front office should get a deal done.

Explore creative trade possibilities involving longer-term contracts

One of the biggest obstacles to retooling the Cubs' current roster is that the team has a lot of long-term contracts on the books right now. Pete Crow-Armstrong and Nico Hoerner recently signed extensions and aren't going anywhere. Alex Bregman and Dansby Swanson are both under long-term deals that include no-trade clauses. That doesn't leave much room for mixing up the roster on the surface., but there's still every incentive for the front office to try.

While deals involving large contracts are rare, they do happen. Last offseason saw the Mets and Rangers get together on a trade that shipped Marcus Semien to Queens in exchange for Brandon Nimmo. Nimmo even had to waive his no-trade protection with the Mets to put the deal through. Would the Cubs be willing to try a similar change of scenery for Swanson, who has struggled this year and can be replaced internally thanks to Nico Hoerner's strong glove at shortstop?

It's something the Cubs should certainly be thinking about, at the very least. While the return for Swanson would surely be a veteran on a hefty contract of his own, someone like Atlanta's Sean Murphy or Houston's Josh Hader might fit the team's needs more than Swanson at this point. Hoerner would be able to take over shortstop, opening second base for a youngster like Matt Shaw or Pedro Ramirez. A free agent replacement like Brandon Lowe would be another intriguing option.

This speculation about Swanson is one example of how the Cubs could look to shake up their lineup, but it's far from the only one. If the club is interested in getting that sort of deal done ahead of 2027, however, they would be wise to start exploring those conversations right now. Trades often take several rounds of negotiations before they actually come together, and that's even more true of deals this complex. Trading a veteran in November could easily require groundwork to be laid in June.

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