The Kris Bryant Dilemma

Back in 2013, when the Cubs drafted Kris Bryant, there was hope that he would be able to hold down third base at Wrigley Field for more than a decade like Ron Santo did.

This was always going to be tough to accomplish with Scott Boras as his agent and the Cubs didn’t help matters with the service time issue they created by delaying his arrival to Chicago in April 2015.  Bryant did everything he was supposed to by winning the Rookie of the Year and Most Valuable Player awards in his first two seasons. A three-time All-Star, the only real blemish on his career to this point has been the injury-riddled 2018 season.  Once healthy, he bounced back with a 2019 season that was on-par with the rest of his career.

We now find Kris Bryant with two years of team control remaining and finally going through the grievance process regarding his service time. The Cubs are hopeful to get some of their core group signed to extensions before they hit the open market after 2021.  Bryant is at the top of the list, but has his extension been D.O.A. since April 2015? It’s easy to think that all of the success he has experienced in Chicago would be enough to keep him on the North Side.  Boras’ whispers in his ear could outweigh that though.  It is no secret that Boras only cares about one thing- the almighty dollar.

The Cubs delayed the realization of that money by securing Bryant’s service for an extra year. This can all be saved though, by the Cubs opening up the vault for Bryant.  To further complicate things, Boras doesn’t like to do extensions and prefers his clients to hit the open market so that he can break out his binders and secure the highest payday possible. Let’s say Bryant makes it to that point at the Cubs are left hung out to dry.  All they will have to show for it is a compensation pick and no real immediate replacement for his level of production.

What do they do?  Tom Ricketts made his rounds on Chicago sports radio recently making his case for sustained success.  Everyone would like to have Bryant around for many years to come. The front office needs to gain a real grasp on just how much Bryant wants to continue his career as a Cub once he becomes a free agent.  They also need to figure that out due to one last complication: Anthony Rendon.

Rendon has been just as good as Bryant and will be signing a lucrative contract with what many expect to be a new team this winter.  There are many across social media that would like to see the Cubs sign Rendon but that won’t be happening, well, not with the current direction of the team.  This, however, is their chance to secure a replacement for Bryant that doesn’t involve a drop off in production.

Don’t take this as demand that Bryant has to be traded. He doesn’t.  With sustained success in mind, they need an answer out of Bryant. They have money earmarked for him and if it won’t be going to Kris it needs to go to a player like him while they still can.


If you feel that he legitimately won’t be staying, get the best package you can for him and go sign your MVP-caliber third baseman. Keep him or trade him, either way, the Cubs need to be able to move forward with the best team possible for many years to come.

Featured Image: Ross D. Franklin/ AP Photo

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Residing in the Cubs-Cardinal War Zone that is Central Illinois, I am a married father of three mini-humans. When ... More about Trevor Hipsher