4 moves that took the Chicago Cubs from champions to sellers

(Photo by Jonathan Daniel/Getty Images)
(Photo by Jonathan Daniel/Getty Images)
4 of 4
Next
(Photo by Patrick McDermott/Getty Images)
(Photo by Patrick McDermott/Getty Images) /

The Chicago Cubs are below .500 at the All-Star Break for the first time since 2014 when they were at the end of a full on tear down and rebuild.

An 11-15 April found the Cubs at the bottom of the NL Central.  A scorching hot 19-8 month of May provided a brief respite from the looming disaster of June, a month nearly all saw coming. Chicago somehow maintained a hold on first place all the way to June 23.  It was a tenuous lead of one game, but they clung to the top spot in the division.

Then like boxer Tom King in the Jack London short story A Piece of Steak, the Cubs, hammered by injury and denied since season start of their best pitcher and the best backup catcher up in MLB, finally buckled under the repeated blows of three road trips and 25 games against top contenders.

The North Siders wobbled out of a 12-16 June in second place. Then they were cold cocked by the Reds and Phillies. By the time St. Louis rolled into town the Cubs were begging for mercy.

Well, when you trade your top-of-the-rotation pitcher and a switch-hitting backup catcher in baseball for a number four guy and a package of teenagers – and that’s your only real move, what did you expect?

Everyone sees the sell-off coming.  Are we surprised?  But it wasn’t supposed to be this way.  It’s fair to ask, how did it come to this?

(Photo by Nuccio DiNuzzo/Getty Images)
(Photo by Nuccio DiNuzzo/Getty Images) /

Chicago Cubs: Number 1 – The decision to sign Jason Heyward to a mega-deal

How bad is Jason Heyward’s  eight-year,$184 million deal? Really, really, bad.  In 2021 Heyward’s contract carries the 23rd-highest AAV in all of MLB.  All that for a lousy slash of .249/.329/.384 and a .713 OPS.

But the worst part of this deal is the downstream decisions that it created.  First, it meant the Cubs passed on signing Nick Castellanos after 2019.  Is there a Cubs fan who wouldn’t have preferred Castellanos over Heyward at that point (or even still today)?

More from Cubbies Crib

Then, pinned up against the 2021 luxury tax threshold, the Cubs were forced to part with Yu Darvish’s $21 million AAV deal at a discount. That’s led to all kinds of issues – most notably a glaring hole atop the rotation and a merry-go-round behind Willson Contreras for the backup catcher role.

Without a doubt, for its longevity, cost, and lack of performance, the Heyward contract is the worst free agent signing in Cubs history.

Chicago Cubs: Number 2 – Theo Epstein broke his own rule about trades

The Cubs were in the hunt for Justin Verlander.  We know that now.  Worse, it seems he wanted to come to the North Side.

Chicago traded for Jose Quintana before Verlander went to Houston but that doesn’t mean the team wasn’t in the hunt beforehand.  Epstein once said that the worst time to make a trade is when you believe you have to.

But he did just that in 2017, sending Dylan Cease and Eloy Jimenez to the South Side for Quintana.  A trade that served no real purpose because the only starting who wasn’t on the 2017 squad from 2016 was the number five guy, Jason Hammel.  Plus the Cubs had Mike Montgomery who was doing fairly well for a number five guy.

(Photo by Meg Oliphant/Getty Images)
(Photo by Meg Oliphant/Getty Images) /

Chicago Cubs: Number 3 – Not drafting enough high quality pitching

Epstein and the front office, from 2012-2014, adopted a “draft the hitting, buy the pitching” approach. That works, but only for a while.  Then baseball economics begins to bear down.  Your hitters start getting paid, your MLB pitching is already expensive. By 2019 with both Lester and Darvish on the roster, the Cubs were paying for all of it.

Something had to give.  It did and Darvish is in San Diego. Now we’re hoping that Adbert Alzolay and Zack Davies can hang on in the two and three spots while the Cubs lurch around to fill the four and five spots.  That has taxed an outstanding bullpen to the point of exhaustion before we even reach the dog days of summer.

Since 2012, the only pitcher drafted by the Cubs that has broken into the rotation is Alzolay.  Cease was sent crosstown for a now departed Quintana and Darvish netted Zach Davies.  Now, consider a rotation with Darvish, Hendricks, Alzolay, and Cease and the consequences of those earlier moves bear down hard.

(Photo by Brian D. Kersey/Getty Images)
(Photo by Brian D. Kersey/Getty Images) /

Chicago Cubs: Number 4 – Creating gaping holes in the lineup

Then there are the unending roster errors. This starts with the unwillingness to re-sign Dexter Fowler.  In 2017 five different Cubs batted in the leadoff spot. Chicago has continued to play leadoff man roulette ever since. That’s no way to build a roster – or set up your big hitters for success.

On top of that there were these acquisitions of dubious and downright awful distinction since 2019:

  • Tony Kemp, Daniel Descalso, Robel Garcia, Carlos Gonzales, Martin Maldonado, Cameron Maybin, Steven Souza, Jr., Jose Martinez, Tony Wolters, Jose Lobaton, Austin Romine, Eric Sogard and Robinson Chirinos

Most I have no idea why they were signed, others were signed out of desperation because we need a back up catcher (not to belabor the point).  But since 2019 we’ve surrounded a core of really good baseball players, with, well, crap.

Next. Who will be the first Chicago Cubs player traded ahead of the deadline?. dark

So here we are at the All-Star Break in 2021, sellers of the last of the World Series champions that were part of the youngest team to ever win the Fall Classic. I don’t think any of us thought on that fall night in 2016 that it would come to this.

Next