5 big questions facing Jed Hoyer as he takes over Cubs

Should the Cubs trade Kris Bryant this offseason?

(670 The Score) New Cubs president of baseball operations Jed Hoyer has his work cut out for him, as he has been tasked by with keeping the organization highly competitive at the big league level while replenishing the farm system and showcasing fiscal responsibility amid an unstable economic climate across the league during the pandemic.

With Hoyer having taken over, here are five big questions for him to answer.

Which iconic Cub(s) should be traded?
When evaluating a core that helped them win the World Series in 2016, the Cubs must separate the emotional aspect from their present circumstances. Third baseman Kris Bryant, shortstop Javier Baez, first baseman Anthony Rizzo and outfielder Kyle Schwarber have all been core players but are set to hit free agency after 2021.

On Monday, Hoyer acknowledged the Cubs aren’t in a financial position to retain all four of those players, meaning trades to recoup value are on the team’s radar this offseason. Of course, that doesn’t mean it’s a simple equation when evaluating who stays and who goes in a possible trade. The Cubs must balance the price it would take to retain each player on a new contract, the value they could receive in a trade, the replacements they have internally and what options would be available externally.

What lies ahead in Bryant’s future?
The Cubs listened as the Braves and Phillies expressed interest in trading for Bryant last offseason. Soon, the rumor mill will fire back up again.

The Red Sox have previously kicked the tires on Bryant with the idea of moving him off third base and to another position, but the sides never matched up further on names in their discussions. Bryant also will have a strong appeal to the Nationals, who need to beef up their offense after going 26-34 and missing the playoffs this past season.

Bryant, who turns 29 in January, is coming off a rough 2020 season in which he hit .206 with four homers, 11 RBIs and a .644 OPS in 34 games as he dealt with various injuries. He’s expected to make close to $20 million in 2021, which would represent the third-biggest salary for the Cubs in 2021 behind outfielder Jason Heyward and right-hander Yu Darvish.

How do Cubs obtain contract-controllable pitching?
The Cubs’ payroll has been largely used on pitching over the past six seasons, dating back to when they inked left-hander Jon Lester to a $155-million deal ahead of the 2015 campaign. The Cubs also added Darvish, Tyler Chatwood and Craig Kimbrel in free agency and traded for Jose Quintana and Cole Hamels in the past half-decade. All were significant financial investments.

Lester, Quintana and Chatwood are now all free agents, leaving the Cubs with holes in their rotation. What the Cubs need to do is sign or trade for pitchers at a less significant cost than in past years who they some semblance of contract control over moving forward. It’s a hard goal to achieve, as all teams have that desire.

Alec Mills and Adbert Alzolay will compete for rotation spots in 2021, and prized prospect Brailyn Marquez has a chance to make the team out of spring training. Even if those individuals perform well and the Cubs’ hopes pan out, they’ll still need more pitching help.

Obtaining pitching will be a requirement for the Cubs in any trade of Bryant or someone else. One of the items on Hoyer’s wish list is also adding power arms in the bullpen.

Who will be Hoyer’s right-hand man?
Hoyer has embarked on a search for a new general manager whom he hopes can complement him in the way he did Theo Epstein for the past nine seasons. The Cubs will seek someone currently outside the organization, Hoyer said without providing a timeline on when a hire will be made.

Diamondbacks assistant general manager Jared Porter could be a candidate. Porter worked with Hoyer while they were with the Red Sox and then also as the Cubs’ director of professional scouting/special assistant for two seasons.

What's Hoyer’s leadership style as the Cubs’ baseball boss?
Hoyer was always well-respected by the baseball community while he was the No. 2 man in the Cubs’ front office.

Behind his friendly demeanor and easy smile is a tough negotiator and a figure who has had a strong influence on the Cubs’ day-to-day operation for almost a decade now. And while he learned plenty from Epstein, Hoyer will now lead in his own style. What exactly that is like remains to be seen, but Hoyer will look to find his voice as he leads the Cubs into a new phase.

Bruce Levine covers the Cubs and White Sox for 670 The Score. Follow him on Twitter @MLBBruceLevine.