Trading Kris Bryant and/or Willson Contreras is a mistake

I’m not going to sugar coat it, as the Winter Meetings have all but just begun my frustrations with the Cubs this offseason are tremendously high. For big market teams, the Winter Meetings are a feeding frenzy. It’s not a matter of if, but how much cash these top-notch owners are willing to fork over in order to sign the blue-chip free agents.


With the meetings just beginning, it already feels like the Cubs are all but out on pursuing any big-names on the market. While other teams are opening their checkbooks, the Cubs are opening up their roster to trades, trying to get rid of their most valuable players and still stay relevant as contenders.


That’s a lot of beating around the bush so I’ll just come out and say it. Tom Ricketts and the Chicago Cubs have shut the window on the 2020 season and are looking towards the future. Ricketts claims the team, the way they’re built should be contending for championships every year, yet he’s afraid of what that might cost him.

There are some very clear cut, defined problems with this team. They need a center fielder, second baseman, leadoff hitter, a starting pitcher, and help with the bullpen. For a big market team, those roles should not be hard to fill. In fact, over the course of a week at the Winter Meetings, the Cubs both could and should be able to resolve those issues.


The team’s expected 2020 payroll is right around $200 million. You would think that should be enough to contend, but it’s not, as we’ve seen over the last 2 years when the Cubs won 95 games and were bounced in the Wild Card, and the following year won 84 games and missed the postseason completely. If $200 million isn’t enough then raise the bar. It’s not going to cost you $100 million more to fix the issues on this team. I’ve found multiple ways for far less money.


The team, the franchise, the front-office have set the standard for where the expectations should be. As fans, we sit in denial and say, “Chicago is not Kansas City and the Cubs are not the Royals,” after they went from winning the World Series in 2015 to 59-103 in 2019.

Or are they?


No, they’re not. The Chicago Cubs franchise is valued at $3.1 billion, which is just a tiny fraction more than the $900 million it cost Ricketts to buy the team in 2009. What it must be like to turn a $2.2 billion dollar profit in 10 years.


With all that money, the Cubs are showing up at the Winter Meetings with dirt under their fingernails, a coin cup in their hand, and their most raggedy designer suits. As they cry broke, buried in their pocket is a sandwich baggie full of gold they’re looking to trade for scraps of silver and bronze.


This all makes sense because when you think about it, the first lesson they teach in business school is to trade away your 2x All-Star catcher and former Rookie of the Year and MVP third baseman for a mid-level rotation starter, and a couple of (as Blake Snell would say) “slapdick” prospects.


A lot of people are making the argument, “well we wouldn’t resign Bryant anyways, so might as well get something for him, right?” Wrong. Tell me why we can’t resign him? If everything goes in the Cubs favor with the arbitration hearing, Bryant will be a free agent after the 2021 season. After that season, the Cubs will have been freed of the Jon Lester contract, Quintana trade, Kimbrel will be owed just $1 million if he has a repeat performance, and Contreras will still be in his second year of Arbitration.

The problem with the Cubs is not a shortage of money, God no. It’s that the money they’ve spent hasn’t necessarily been spent well. The team feels hamstrung over still owing Jon Lester $20 million, Jason Heyward $21 million for his pep talk during the rain delay, and $22 million to Yu Darvish for what was a stellar second half of the 2019 season but not much outside of that.

As a big market team, which the Cubs are despite their internal mixed beliefs, the goal should be to not only reward your best players but also (and I know this is a crazy concept) keep the best players ON YOUR TEAM.


I already know the Cubs trading Kris Bryant is a foregone conclusion, I’m just trying to prepare myself for when he shows up to Wrigley Field in a Phillies jersey and peppers baseballs all over the park. This is a trade the Cubs are going to end up regretting in the long run, I can just feel it.

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