Winter Meetings Day 1: What will the Cubs do with Kris Bryant?

By Thomas Gibbons

Should he stay or should he go?

As the MLB Winer Meetings began Monday in San Diego, the talk surrounding the Chicago Cubs has been about their restricted payroll and the unknown future of their star third-baseman Kris Bryant.

The Cubs failed to make the playoffs last season for the first under Joe Maddon. With that and other reasons, Cubs President of Baseball Operations and Maddon decided to part ways. Maddon will go down as the best Cubs manager to date for ending their World Series drought and bringing a winning culture to Chicago.

In comes David Ross. A member of the Cubs 2016 World Championship team, Ross had previously been in a advisor role with the Cubs along with his work in the MLB booth at ESPN. Now, Ross is the next manager of the Cubs and is under plenty of pressure to help guide the Cubs back to the postseason.

With the Winter Meetings in full-swing, there will be a lot of rumors and signings this week. This biggest signing of the offseason happened Monday afternoon with World Series MVP Stephan Strasburg staying with the Nationals for $245 million over 7 years, the biggest annual average value in MLB history. Other key signings this offseason include Yasmani Grandal signings with the White Sox ( 4-years, $73 million), Mike Moustakas heading to the Reds ( 4-years, $64 million) and Zach Wheeler heading to the Phillies for $118 million over 5-years.

Now for the meat and potatoes. Bryant has been at the forefront of Cubs news coming out of San Diego. The 27-year old former MVP is entering another year of arbitration and will not hit free agency for two more seasons. However, the Major League Baseball Players Association, on behalf of Bryant, field a grievance in late October regarding the alleged manipulation of his service time that prevents him from becoming a free agent until after the 2021 season.

This holdup on the ruling of Bryant’s grievance could or could not be a roadblock for interested clubs. The manipulation of his service time refers to Bryant starting the 2015 season in Triple-A so the Cubs could have one more year of control.

There were reports back in 2018 that Kris Bryant tuned down a contract extension from the Cubs worth around $200 million. Being a Scott Boras client, players usually hit free agency and seek the highest bidder. Bryant has been a huge part of the Cubs success in Chicago and while they have tried to lock up one of their franchise players, trading him before they lose him to free agency may be the way to go.

Jesse Rogers, covers the Chicago Cubs for, has throw out there an interesting prediction of what the Cubs will do with Bryant. “The Cubs will trade Kris Bryant to the Braves for Max Fried and top prospects.” Fried, 25, earned a 17-6 record with a 4.02 ERA last season. Epstein and Co. have failed to develop young starting pitching within the organization. Fried would fill a need. As for prospects in the Braves system, outfielders Christian Pache and Drew Waters are intriguing players and a weakness on the Cubs roster. Kyle Wright and Bryse Wilson are other pitchers in the Braves system are other players worth looking into.

So would a deal involving Fried, Pache or Waters and another young pitcher be a green light for Epstein? Hard to say. The Cubs need at both of those positions says yes, but the Cubs should be looking for the highest bidder if they are really motivated to move Bryant.

As reported by Bruce Levine and others, the Phillies have inquired about Bryant but no concrete talks have begun.

NEW DEVELOPMENT: According to Ken Rosenthal of The Athletic, The Cubs are awaiting the signings of free-agent third basemen Anthony Rendon and Josh Donaldson, believing the losers of those sweepstakes will be prime targets for a Kris Bryant trade.

NEW: As of Tuesday morning, Jon Morosi of MLB Network reported that the Nationals are another team who have inquired about Bryant.

Other notes from the Winter Meetings

  • It does not appear the Cubs and Nicholas Castellanos are headed for a reunion. Quickly becoming a fan favorite last season, the 27-year old outfielder belted 16 home runs and posted an OPS of 1.002 (!) in 51 games for the Cubs has drawn interest from a lot of teams, the Chicago White Sox being one of them. Given the Cubs payroll constraints, Castellanos’ return to the North Side is unlikely unless the Cubs can make some room.
  • According to Levine of 670 theScore, the Cubs have interest in Dallas Keuchel. The 31-year old left-hander posted a 3.75 ERA in 19 starts with the Braves last season.

Stay with Windy City Chronicle all week for all the latest from the Cubs and White Sox at the Winter Meetings. New writer Luke Stanczyk has joined the team and will be all over the White Sox when news strikes!


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s