Top three reasons the Chicago Cubs have seen their window start to close

Chicago Cubs: Poor decisions in free agency are proving costly

I’d say at this point, two of Theo Epstein’s big free agency moves paid off: Jon Lester and Ben Zobrist.

Lester, of course, did exactly what the Cubs hoped for when they signed him prior to the 2015 campaign: anchor a rotation and bring a winning pedigree to a ripe, relatively inexperienced clubhouse. He did just that, finishing runner-up in NL Cy Young voting in 2016 and racking up nearly 1,000 regular season innings in his first five years in Chicago.

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But age is rearing its ugly head and after a disappointing 2019 performance, Lester will look to rebound to a degree in what could be the final year of his deal.

Zobrist, of course, helped write the most historic chapter in franchise history, delivering the go-ahead knock in Game 7 of the World Series and turning in the most consistent at-bats pretty much without fail in his four years with the Cubs. So, again, worth every penny – and that’s not up for debate.

But if you look past these two, Epstein has made some pretty questionable calls in free agency. Jason Heyward seems to hold a special place in most of our hearts, but it’s pretty much impossible to make the case he’s worth the $184 million the team is paying him over the course of his eight-year deal.

Brett Anderson was a flop in his time with the club, Tyler Chatwood and Yu Darvish both struggled mightily in their first year before rebounding nicely in year two (so, I suppose the jury is still out in that regard, but still).  Brandon Morrow stands out as a particularly high-risk, high-reward move that didn’t pan out in the slightest as he threw just half a season (35 outings) over the course of his two-year, $21 million deal. Oh, and they’ll pay him another $3 million to buy out his 2020 team option, too. So that’s nice.

I will admit – while Epstein has swung and missed quite a bit in free agency, he’s made some absolutely mammoth trades, bringing in the likes of Rizzo, former Cy Young winner Jake Arrieta and the man who shut the door in 2016, Aroldis Chapman. So don’t get me wrong – he’s definitely made impactful moves in his time here.

The point I’m trying to make is simple: if you’re looking for somewhere to place the blame for the Chicago Cubs standing on the precipice with just two years of control left with most of their main guys, look no further than the front office.

It’s failed to institute a system that develops pitching, which has led to the team piecing together pitching staffs and trading valuable young pieces to keep the team afloat in recent years. The Cubs have spent money ineffectively under Epstein – and, although you can definitely be upset ownership didn’t pump more money into the baseball ops budget last winter – you can’t be happy with how Epstein has spent the record-level funds at his disposal, either.

With Maddon out, the pressure is at an all-time high for this regime. There’s nowhere else to hide and no one else to take the blame for shortcomings. This offseason may very well be the make-or-break for Epstein and the Cubs’ hopes of building a long-term championship threat. Let’s hope he’s up for the challenge.