The Chicago Cubs’ offseason approach will soon start to take shape. Now that the World Series has ended, the Cubs face important decisions.

Their roster will largely stay intact, with Kyle Tucker holding the honor of being their most notable free agent. A season that ended one win shy of the National League Championship Series shows how well-constructed the 2025 version was in, at the very least, accomplishing their goal of returning to the postseason for the first time since 2020.

The Cubs fell short, though, of the deep October run they envisioned. So how do they replicate a 90-plus-win season and get farther in the playoffs next year?

Here are three key questions the Cubs face this offseason.

1. What approach will they take to upgrade the roster?

The core of the roster, namely

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