UPDATE: The Chicago Cubs are at a critical crossroads following a fiery postseason taunt from the Milwaukee Brewers. After clinching the National League Division Series on Saturday, Brewers reliever Trevor Megill waved an “L” flag at the Cubs, intensifying their longstanding rivalry. This moment could serve as motivation as the Cubs prepare for the 2026 season.
With the Brewers advancing to face the Los Angeles Dodgers in the NL Championship Series, the Cubs have their eyes on rebuilding and strengthening their roster. Cubs President Jed Hoyer faces several pivotal decisions that could shape the team’s future as they aim to capitalize on a successful 2025 season.
Hoyer is considering six potential strategies for the Cubs, each with significant implications for the upcoming season. Here’s a breakdown of the most pressing options:
1. Run It Back
Re-signing star outfielder Kyle Tucker is at the top of Hoyer’s list. Keeping the majority of the 2025 roster intact while making minor adjustments could push the Cubs into luxury-tax territory. Despite a mixed performance at Wrigley Field, where he hit just .236, Tucker’s return could help secure another 90-plus win season, positioning the Cubs as strong contenders for the playoffs.
2. Leave the King, Take the Cannoli
If Tucker departs in free agency, the Cubs might turn to Owen Caissie or Seiya Suzuki to fill the right field spot, allowing emerging star Moisés Ballesteros to take over as designated hitter. This scenario could still see the Cubs competing for a wild-card spot with an anticipated 85-plus wins, especially with a revamped bullpen and rotation.
3. Schwarbomb Redux
Bringing back free agent Kyle Schwarber could be a game-changer for the Cubs. With the financial room created by not re-signing Tucker, Schwarber’s power hitting at age 33 could energize the lineup, keeping the Cubs competitive in the division and aiming for the postseason.
4. Rebuild 3.0
Hoyer may opt for a more radical approach by trading away veterans while promoting younger talent like Kevin Alcantara and Jonathon Long. This strategy aims to balance immediate competitiveness with future potential, relying on a solid rotation anchored by Justin Steele and promising prospects.
5. Back Up the Truck
A complete overhaul could be on the table, with only top prospects Cade Horton, Pete Crow-Armstrong, and Nico Hoerner safe from trades. This scenario would allow the Cubs to reclaim financial flexibility while focusing on rebuilding towards a more competitive future.
6. Project 2032
In the most drastic move, Hoyer could consider a full rebuild, trading away even the brightest stars for future prospects. This long-term investment strategy could set the Cubs up for success by 2032, echoing past tactics that brought championships to the franchise.
The Cubs’ decisions will have lasting implications, not just for the team but for the passionate fanbase eager for a World Series title. As the offseason approaches, the organization must weigh its options carefully to ensure they are ready to respond to the Brewers’ taunts on the field.
Fans and analysts alike are watching closely as the Cubs prepare for what promises to be an electrifying offseason. The clock is ticking, and the team’s direction will become clearer in the coming weeks.
