Chicago Cubs: Theo Epstein whiffed last winter – and it might not matter

In a rare miss, Theo Epstein whiffed last offseason in signing Tyler Chatwood and Yu Darvish. Still, if the Chicago Cubs overcome, it might not matter.

Unmitigated disaster.

Normally, when I look at the Chicago Cubs through the lens of either a writer or fan, I try to keep at least some semblance of optimism. But when it comes to Tyler Chatwood and Yu Darvish, we’re at the point where that’s no longer possible.

Despite a demotion to the bullpen in late July, Chatwood leads all Major League pitchers with a staggering 93 walks (at a rate of 8.2 per nine, in case you’re wondering). He had a second chance last weekend and dropped the ball – all but guaranteeing the Cubs hole him up somewhere once rosters expand in September.

As for Darvish, he looking dominant in the first inning on Sunday, even touching 95 MPH on the gun with a heater. But, while warming up before the second inning, he signaled for the trainer and, soon after, requested an MRI. In other words, put a bow on year one of his six-year deal.

But here’s the thing. As bad as both of these players have been, the Cubs somehow hold the best record in the National League. If this team pulls a rabbit out of its hat and somehow reaches its second Fall Classic in the last three years, will anyone care about Epstein’s swing-and-miss offseason performance?

Chicago Cubs: We just lit $20 million on fire

But really.

For what we got out of Yu Darvish this season, we could’ve thrown $2 million at Lackey and let him serve up dingers for a couple months. At least we’d get some red-blooded Texan quotes to take the edge off.

Instead, we’re staring five more years straight in the eyes, praying the Japanese right-hander comes back healthy and ready next spring. And, if we’re being honest, we have no cause for optimism based on what we saw this year.

Suffice to say, I don’t see him utilizing his opt-out clause at season’s end. This is a long-term love affair and it certainly didn’t start out on the right foot. When the dust settles, the Darvish signing could sit right alongside the contracts Epstein doled out to Carl Crawford (seven years, $142 million) and John Lackey (five years, $82.5 million) in Boston.

Let’s hope it doesn’t play out that way.

Jon Lester and Cole Hamels aren’t getting any younger. Jose Quintana and Kyle Hendricks both took steps in the wrong direction this season. Mike Montgomery its currently sidelined with inflammation in his throwing arm.

If this is the Darvish we get for five more years, the Cubs could be in real trouble.

Chicago Cubs: The pitching is there – it just needs to perform

Most teams would peek at the Cubs starting rotation in a state of envy. You’ve got three-time World Series champion and five-time All-Star Jon Lester at the helm. His last time out, he turned in his best outing of the second half which, hopefully, means he’s back on-track.

Then, midseason pick-up Cole Hamels follows. This guy has been the best pitcher in baseball since joining the North Siders, matching what Justin Verlander did in his first four Astros starts a year ago blow-for-blow. Given the low-level return Chicago gave up to land him, this deal could prove to be a steal by season’s end.

And, then, you have the duo of Kyle Hendricks and Jose Quintana. We all know what each of these guys is capable of. As has been the case with the Cubs, as a whole, they just need to go out and execute. 

But heading into a postseason series with some combination of Lester, Hendricks and Hamels with Quintana waiting in the wings? The Cubs could certainly be worse off. For now, it’s just a matter of getting to October.

With Mike Montgomery sidelined and no clear replacement given Chatwood’s struggles, that’ easier said than done. But if the ‘Big Three’ step up and pitch well down the stretch, no one is going to be talking about Yu Darvish by season’s end.