12 Days of Cubsmas: One World Series ring in the Theo Epstein era

We’re back with the 12 Days of Cubsmas and I can already see someone firing up in the replies that this should have started on Christmas Day and then gone 12 days. While that is technically correct I sort of figured most of you weren’t hanging out on BCB clicking refresh every five minutes on Christmas waiting for this year’s Days of Cubsmas. Besides, it’s Cubsmas, not Christmas. Like all things in 2020, it’s just going to be a little different.

Speaking of 2020, what a year. This year’s celebration of Cubsmas will reflect the mixed bag we’ve all been living through. Don’t get me wrong, there are still things to cheer for throughout the next 12 days of posts - there just will also be some things to reflect on - like today’s post: One World Series Ring in the Theo Epstein Era.

Before we get too much further in the specifics, let’s just relieve the most perfect moment of baseball one more time [VIDEO]:

It was perfect and exactly what Theo promised. After over a century of futility the longest drought in professional sports ended and the most successful era of Cubs baseball in my lifetime reached its apex.

Let’s be really clear, the last five years of Epstein’s tenure with the Cubs were nothing less than a Golden Age of Cubs baseball, even with “only one” ring. I get it, there are naysayers out there. And everyone wants to look smart with contrary takes, but unless you are over 110 years old, you’ve never seen a more successful period of Cubs baseball. Period.

There was a stretch of 12 consecutive years where the Cubs played over .500 baseball with two World Series wins between 1903 and 1914. There was a period of 14 years in a row where the Cubs played over .500 baseball with no World Series wins (but four NL pennants) between 1926 and 1939. And then there is futility. While the Cubs managed a record over .500 for six seasons in a row during the heydays of Ernie Banks, Billy Williams, Ron Santo and Ferguson Jenkins that brilliant team from 1967-1972 had no postseason appearances. The only other stretch of over .500 baseball with multiple postseason appearances was the last six seasons, which included two trips to the NLCS, one World Series win, and five trips to the postseason (admittedly, the change in postseason format is a key difference between that 1967-72 team and the last six years).

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We can quibble in the comments about free agent contracts and missed trade opportunities. We can, and should, take stock of the talent that left the Cubs farm system for very little in return. But there were also brilliant deals. Jon Lester is probably the best free agent signing in my time as a Cubs fan, turning Steve Clevenger and Scott Feldman into Jake Arrieta and Pedro Strop was one of the most amazing magic tricks this side of Javier Báez. While it may pain Cubs fans to see Gleyber Torres and Eloy Jiménez in black and white instead of Cubbie blue, it’s also worth noting that there is no Cubs World Series win and no 2017 trip to the NLCS without those deals. Furthermore, the only reason the Cubs had those chips to trade is Theo’s masterful understanding of the international free agency before it was reformed.

It’s incredible that nine years happened so quickly. I still remember hanging out in the teachers’ lounge in a suburb of Boston when the news broke. My co-workers, all Red Sox fans, were devastated and I literally did a jig, complete with a Ron Santo style heel kick.

It may be a few years before the Cubs give me a reason to dance in my office again, but championship banners are forever. Before we get too far down the rabbit hole of what’s already been a brutal offseason, let’s thank Theo Epstein one last time.

On the First Day of Cubsmas my true love gave to me: One World Series Ring in the Theo Epstein Era.