From 2010 to 2014, the Chicago Cubs rebuilt with an eye on eventually being competitive enough to win their first World Series since 1908.
They were ready to compete in 2015, in large part thanks to Kris Bryant’s Rookie of The Year season, but they lost to the New York Mets in the Championship Series.
They won it all in 2016, in one of the most exciting Game 7 ever to be played against the Cleveland Indians.
They remained contenders… until 2021.
In fact, their decline began in the 2018 and 2019 seasons: in the former, they were eliminated in the Wild Card game, and they missed the playoffs altogether in the latter.
The 2021 season, if anything, has marked the end of the Cubs’ core: Anthony Rizzo, Javier Baez, Bryant, Kimbrel, and pitcher Zach Davies are going to hit the market at the end of the season, and the club, having admitted they would be sellers at the deadline, is shopping them.
It has been a sad ending to an otherwise great run.
It’s weirdly cathartic watching the Cubs these past couple weeks. You know the rebuild’s gonna happen, but it’s celebrating those still around from 2016.
— Andy Sorensen (@SORENSEN_ANDY) July 28, 2021
The Cubs already admitted defeat near midseason, as they are 50-53.
They are 10.5 games behind the division-leading Milwaukee Brewers.
How the Cubs could have planned better for the end of their core run?
It’s a complex question.
All Good Things Come To An End
Basically, they stopped paying attention to their farm system and prioritized veteran free agent signings while ignoring their own stars.
The Cubs’ minor league system is ranked in the bottom half.
MLB’s preseason ranking had Chicago as the 22nd best system out of 30 teams.
You could say it improved a bit after the draft, but it remains a bottom-half system.
Unfortunately, they also signed the wrong deals.
They really put a lot of eggs in Craig Kimbrel’s basket before the 2019 season, when they decided to give him that lucrative three-year, $43 million contract.
Kimbrel was very bad in 2019 and 2020.
They also signed veteran Yu Darvish to a six-year, $126,000,000 contract in 2018, and while he was good with the Cubs, these kinds of moves hamstrung their payroll flexibility.
Darvish ended up being traded in the 2020-2021 offseason.
Veteran Jon Lester was also costly and ineffective after the first two seasons of his Cubs tenure.
Additionally, the few times they put their eye on young talent, they failed miserably (example: Jason Heyward in 2016.)
Starting All Over Again
Why do we say the Cubs could have planned their core end better?
Because they largely ignored contract extensions to their best players.
They did extend Rizzo way, way back in 2013, but talks went nowhere when they tried to extend him again before his free agency becomes effective, after the 2021 campaign.
But they couldn’t negotiate extensions with Baez or Bryant, or Kyle Schwarber, who has once seen as part of the future but got non-tendered after a bad season (2020) that was atypical for everybody.
Schwarber landed in Washington and is having a terrific year.
To sum up, they extended Rizzo a long time ago, and pitcher Kyle Hendricks, and those were good moves.
But they failed to lock down a Rookie of the Year and MVP, and a dynamic, two-way talent like Baez.
Since their deals expired around the same time, Chicago is now looking at a massive rebuild because extensions are now apparently off the table with all the pending free agents.
NEXT: 3 Top Moments For Kris Bryant During Cubs Career
Rebuild won't be easy for Cubs. It's going to take time.
— MLBExecutiveBurner (@HotStoveintel) July 28, 2021