How Winning Has Hurt Chicago Cubs Plans In 2021

If there was ever a year where the Chicago Cubs would have been okay with not contending, this 2021 season would have been it, and here’s why.

The majority of the Cubs’ core is set to hit free agency after the season, and the team will likely have a completely different look next year.

While Chicago can attempt to retain some of its stars, several are bound to walk.

The Cubs likely had a plan coming into the season which has been derailed by the fact that the team has vastly exceeded expectations so far.

Waking up to the first place Cubs like pic.twitter.com/TCRMItdvWJ

— Bleacher Nation Cubs (@BleacherNation) June 10, 2021

The Cubs have managed a first-place 35-27 record through two months. So, that begs the question…

What Was The Plan?

Presumably, the Cubs would have liked to have been able to flip their expiring stars’ contracts into some value at the trade deadline.

The following players are among the notables set to hit free agency after the season: Kris Bryant, Javier Baez, Anthony Rizzo, Dan Winkler, and Zach Davies.

Jake Arrieta has a club option.

There are more, but those are the big names.

Within that bunch, you’ve got the Cubs’ two best offensive players (Bryant and Rizzo), a third extremely solid offensive player (Baez), a reliever who has been lights-out this season (Winkler), and a starting pitcher who has a very good track record (Davies).

There is a lot of trade value in there that the Cubs will likely now be reluctant to get rid of given the team’s success this season.

Now let’s not get carried away—the Cubs can’t be too upset with their current position.

An organization will never complain about having a contending team.

But the fact that Chicago is contending this year might ultimately hurt the organization’s future, considering the amount of young talent that a deadline fire sale could have brought to Chicago.

Could They Still Do A Soft Sell At The Deadline?

Generally, soft sells don’t make a whole lot of sense.

It always feels weird when an organization ships off important pieces at the deadline, then acts like they still hope to contend for a title that season.

If the Cubs want to sell, they should sell.

In which case they should get rid of as many expiring deals as possible and maximize the return, effectively punting on the 2021 season.

That’s not a move that would make fans happy at all, but it is in an option.

Kris Bryant, on Trade Deadline unknowns for Cubs:

"I don't put any much thought into it. It's wasted energy. Whatever happens is going to happen. But it's cool to hear, when I'm running out to the outfield in Wrigley, all the fans saying they want me."

— Jordan Bastian (@MLBastian) June 8, 2021

Conversely, if the Cubs want to go for it this season, they should give the current group the best chance possible.

That means at the very least keeping the core intact, and possibly adding a piece or two at the deadline.

Whatever Chicago chooses to do, they should avoid being caught in the middle.

Wrap-Up

Let’s reiterate the most important point: it would be silly to call Cubs’ success this season frustrating.

Chicago looks like a team that is capable of winning a title.

That said, the club’s initial plan of selling at the trade deadline is now up in the air.

The Cubs could still do it, but it would be painful to watch the organization dismantle a contending team.