3 colossal questions facing the Chicago Cubs as the offseason begins

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.