Cubs' top 5 offseason questions: How does Cody Bellinger fit? And which free-agent pitchers will Chicago target?

The Chicago Cubs were one of the most disappointing teams of 2024 .

The Cubs have not reached the postseason since Theo Epstein departed following the 2020 season .

The organization must find a way to reestablish itself as a legitimate contender in the National League and quickly.

Here are the five biggest questions facing the Cubs this winter .

The Cubs have room for another big-ticket addition in Chicago without needing to pay the luxury tax.

Early indications out of Boston show that the Red Sox are ready to spend aggressively.

The Cubs need pitchers, so which pitchers could be realistic targets? Is the Cubs ’ infield set, or are more moves coming?.

If the Cubs deem Shaw ready sooner rather than later, might they consider dealing Hoerner to make room for Shaw at second ? It's awfully difficult to determine whether that’s a sensible strategy without knowing just how big-league-ready Shaw is or what version of Paredes the Cubs will get in 2025 .

Shaw isn't the only prospect in the Cubs ' system who could make a difference.