3 colossal questions facing the Chicago Cubs as the offseason begins

With MLB postseason action getting underway on Tuesday, with four games taking place, the Chicago Cubs were, instead, cleaning out their lockers at Wrigley Field and preparing for the offseason.

The Cubs haven't punched their postseason ticket in a full-length season since 2018 and haven't even won a playoff game since the 2017 NLCS. The 2024 campaign, which began with high hopes on the heels of bringing in Craig Counsell to replace David Ross, ended with the team playing to the exact same 83-79 record and missing the postseason by a half-dozen games.

Things have to change this winter if the results are going to be different in 2025. Here are three of the biggest questions facing Jed Hoyer and this organization as the offseason gets underway.

1. Without major free-agent upgrades available, how will Jed Hoyer solidify the catcher position heading into 2025 and beyond?

Miguel Amaya had every chance to establish himself as the long-term answer behind the plate this year. But given his up-and-down performance at the plate, the Cubs can't plan on him being the top man on the depth chart heading into 2025.

Amaya got off to a brutal start at the plate, to the point some wondered if the team would just cut him and move on. He rebounded from a .554 OPS in the first half, hitting north of .300 in both July and August, but September was cruel to the Venezuelan backstop when he hit just .197 in 21 contests.

Despite receiving high marks from the pitching staff, defensive metrics paint a very different picture, with Amaya ranking near the bottom of the league in framing, pop time and caught stealing percentage. If he was an elite defender behind the plate, the bat might not matter as much - but this is a clear area of opportunity for the Cubs and they need to come up with a real solution.

This winter's free-agent class of backstops is less than awe-inspiring, with only Carson Kelly looking like he might be a legitimate option. A more prudent course could be prying away a catcher from an organization with depth at the position (the Athletics, Dodgers and Angels come to mind) - but that will require Hoyer doing something he's never done: parting with top-tier prospect talent via trade.

3. What tier of free agency will the Cubs play in this winter?

It's the question. Period. The Chicago Cubs, should they so choose, have the financial means and resources to go toe-to-toe with the game's highest spenders. The problem, to this point, has been an unwillingness to push those limits, especially when it comes to pursuing superstar free agents.

This winter's free-agent class is headlined by Juan Soto on the position player side of things and Corbin Burnes on the pitching. Both would make perfect additions to a Cubs team lacking that caliber of player, but neither seems like particularly likely pursuits.

Chicago could look to that next level of talent, featuring names like Santander, Max Fried, Pete Alonso and others to shore up the roster - and that feels very doable, especially with upwards of $50 million coming off the books. Hoyer needs to not only improve around the margins, but find ways to make major upgrades to raise the floor of this team. Flexing some large-market financial muscle seems like as good of a place as any to start.