5 biggest questions facing the Chicago Cubs in 2021

For the first time in years, the Chicago Cubs are heading into a season on the outside looking in when it comes to most postseason projections. By most measures, they’re not even poised to win the National League Central.

That alone tells you this club faces a lot of questions as Opening Day draws closer. Throw in an offseason where the organization seemed to spin its wheels and lack a clear direction at times and that’s where we stand.

The biggest question on everybody’s mind, though, at least for the next three weeks, is whether or not Chicago will be able to extend any of its free agents-to-be. Cubs president of baseball operations Jed Hoyer has previously stated he plans on talking with Kris Bryant, Javier Baez and Anthony Rizzo regarding extensions this spring.

So far, though, Bryant says he hasn’t talked with the front office on that front and we haven’t heard anything from either of the others. Baez and Rizzo both make a ton of sense as long-term pieces – and the direction the team takes with them could go a long way in dictating what the next few years look like for Chicago.