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.

Is this the end of the road for the Cubs and Kris Bryant?

No matter what the next few months bring, Kris Bryant will leave a lasting legacy on the North Side. The former first-rounder won Rookie of the Year in 2015, following it up with a World Series ring and NL MVP honors in 2016. From 2015 to 2019, he was one of the most valuable players in all of Major League Baseball.

But coming off a lackluster performance in 2020 and making nearly $20 million in his final year of control, Bryant is a prime trade chip for the organization. All offseason, trade rumors connected the Cubs third baseman to teams like the Braves, Mets, Dodgers and Nationals. But the winter has come and gone and he’s still here in Chicago.

Why did a deal never come to fruition? Because Bryant’s trade value is at an all-time low. He’s coming off the worst season of his professional career, he’s battled injuries the last few years and hasn’t come close to matching his early-career numbers in some time. Both he and the team need him to re-establish himself early on this season.

It’s not impossible for Bryant to play out the season with the Cubs and end up returning on a new deal after testing free agency, but I wouldn’t consider it particularly likely to happen, either. The next three weeks will be critical in determining Bryant’s future in the Windy City.

Cubs: Can Craig Kimbrel turn the page on two rough seasons in Chicago?

Craig Kimbrel was supposed to be part of the solution. Instead, he’s been arguably the biggest problem in the Cubs’ bullpen since signing with the team halfway through the 2019 campaign.

Despite finishing the 2020 season on a high note, the veteran right-hander has been a total disaster on the North Side. He’s struggled to locate his curveball, saw his once-overpowering fastball lose critical velocity and opposing offenses made him pay the price.

Entering the last year in his initial three-year, $45 million contract, Kimbrel has been roughed up early this spring, as well. He’s made just two appearances, but allowed five runs on five hits. Opponents are hitting .556 against him and his 22.50 ERA isn’t exactly a confidence boost.

Like Bryant, right now Kimbrel has very little trade value. Given his age and recent struggles, he’s actually got less value than Bryant, who is still just 29 and is a former NL MVP. His $16 million salary makes him someone Hoyer would undoubtedly like to shed at the trade deadline, but unless Kimbrel gets back on track and shows he can still close out games consistently, he’ll likely finish the year in Chicago.

Cubs: Is this starting rotation ready for the grind of 162 games?

The starting rotation for the 2021 Cubs starts and ends with Kyle Hendricks. He’s the only sure thing out of the myriad of arms vying for a spot in this staff.

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Former Cubs hurler and Cy Young winner Jake Arrieta is back in the fold, but no one seriously expects him to be anywhere near what he was in his first stint with the team. Preseason projections are low on the right-hander. The sad truth? Chicago needs him to at least eat some innings – something he hasn’t done in awhile.

Trevor Williams and Alec Mills will each get a spot in the rotation, as well. Both have looked sharp this spring, but are coming off pretty so-so performances in 2020. Williams has a 5.45 FIP over the last two years and, despite a no-hitter, Mills was erratic and inconsistent last season.

Another offseason pickup, Zach Davies, will look to learn from Hendricks and repeat his breakout 2020 with the Padres. The soft-tossing right-hander was stellar with San Diego and came over in the Yu Darvish trade. Again, being in the final year of his contract, Hoyer could look to trade him at the deadline if the Cubs are out of contention by that point.