Chicago Cubs: Top five moments during the team’s window of contention

While the Cubs’ window of contention” might be over, memories last forever.

Depending on your outlook, it’s either a time for reflection or a time for mourning if you’re a Cubs fan. And, mind you, I’m specifically talking about the Chicago Cubs here and not the bigger issues in the world at large that dwarf baseball right now.  However, if you’re feeling a bit annoyed or frustrated about the direction the team seem to be going, here’s a little Christmas gift from me to you.

The legendary yet totally subjective “Window of Contention” for the Cubs has sparked untold discussions amongst friends, enemies, and baseball people. Was it a failure? Was it a success? Was one title enough? Should it have lasted longer? Is it even over officially?

These existential questions probably won’t keep you up at night, yet they’re questions that linger now that the window seems to be in the process of being replaced. While we don’t know what kind of window will be replacing the old one, we do know that the old one was phenomenal and gave us access to many a great sights while it was at its peak.

So, let’s dust off that not so old window and take a look back at the five best moments during the Cubs most recent window of contention from 2015-2020.

Chicago Cubs: Which signing was more important?

While one was more a hiring than a “signing” per se, both guys had to sign on the dotted line regarding their intentions to join the Chicago Cubs. Many have said that the Jon Lester free agent signing is the best in Chicago sports history, yet one just as important preceded his signing by 38 days. When the Cubs fired poor Ricky Renteria and announced the hiring of the idiosyncratic Joe Maddon, the gauntlet was thrown down to the rest of baseball: the Cubs aren’t just lovable losers anymore: we are for real.

Think what you will of Maddon and the end of his tenure with the ball club, it is undeniable that his unique managerial style enabled the Cubs to win a World Series. He communicated with his players, he was charismatic with the Chicago sports horde, and his lax managerial style allowed many of his young players to flourish. Then again, this was only possible, in part, because of the signing of Lester on December 10, 2014.

Lester brought an ace mentality to the team and his signing signaled a new era in Cubs history. Theo Epstein’s decision to pay the big lefty big money was just the sign many in Chicagoland and beyond needed to take this team for real. It also paved the way for a guy like David Ross to join the flock, a move that’s still paying dividends for the organization.

It wasn’t so much his performance that was important to the Cubs, although Lester did compile a 77-44 record and 3.64 ERA over six seasons with the club. It was the grit he brought, the aura he emanated, and the leadership he personified. This Lester and Maddon debate is sorta like the chicken or the egg discussion: at this point it’s a moot point because we needed them both.

Chicago Cubs: Beating the Cards was a weight lifted

It’s getting harder and harder to remember the vitriol since they haven’t been the Goliath they once were, but it’s still there. For most Cubs fans, there’s still a hatred (or at least a modest or healthy dislike) for the Cardinals that supersedes pretty much everything else when the two teams meet.

At one point, the Cubs could never beat the Cardinals in a big game. Yes, that’s right – never. The Cardinals and their 11 World Series championships and their “Best fans in baseball” were easy targets for Cubs fans’ invective. Chicago was the red-headed stepchild in a terribly abusive relationship. Jealous, annoyed, frustrated, and hopeless, that all changed in the 2015 postseason.

The Cardinals were the favorites due to their 100 win season, but the NL Central actually had the three best teams in baseball that year as the Pirates (dispatched by the Cubs; see last slide) had won 98 and the Cubs with 97 wins.  They all had to face off against once another early in the National League playoffs in 2015, and it was then that the Cubs finally broke through against their older brothers.

After losing the first game in the most boring city on Earth, the Cubs won the next three, thereby punching their ticket to the NLCS. Whether it was Javier Baez and his monster oppo taco or Kyle Schwarber’s moonshot onto the scoreboard, the Cubs showed the Cards who was to be the dominant power in the Central for the next half decade.

Chicago Cubs: You DO remember this one, right?

This might be the outlier amongst the other moments on this list, but it sticks out in my mind as THE defining game of the last six years. I remember thinking before the game, “What the &%$# is Theo thinking and there’s no way Joe is happy with this.”

I remember thinking in the first inning, “What the &%$# was Theo thinking and Joe must be so pissed right now.”

I remember thinking in the second and third inning, “What are we doing running him out there again?!?!?”

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Then, I remember the feeling I had that somehow this was some weird experiment Epstein had devised and then created to test the Cubs resiliency and stalwartness for a possible run to the World Series. I even texted my brother that exact thought.

While it may have been giving Epstein too much credit, running a has-been out there and sticking with him for three innings and a six run deficit was exactly what they needed. When most fans were probably turning off their Sunday Night Baseball, I had this weird feeling the Cubs were going to come back from this 6-0 hole and pull it out.

And, of course, pull it out they did in 12 innings thanks to the heroics of Travis Wood in left field and a Lester walk-off, two-strike suicide squeeze. Whether it was a turning point in believing in Maddon’s wacky and unconventional managing or a consolidated group effort to negate even the worst of organizational decisions in running Brian Matusz out there in the first place, it worked. And the rest, as they say… is history (and the next slide).

Chicago Cubs: The Curse is lifted – and our fandom changes forever

I could just leave this picture here and let you paint the rest of the scene with your mind. Any words I might be able to put down on paper regarding the greatest night in Cubs history would pale in comparison to the feelings all of us felt that Thursday morning in November of 2016.

For most of us, it was a feeling we had never been introduced to. For some, it was a feeling we never thought we’d get the chance to experience.

In one crazy night, the North Siders were able to exorcise over a century worth of demons, putting to bed the notion that they’d always be losers or that they couldn’t possibly win because of a goat or a random dude sitting down the left field line with headphones.

In typical fashion, it did require several home runs, a blown save by the most lockdown of lockdown closers that year, a well-timed comeback, poor managerial decisions, and Willis Reedesque heroics from a guy who hadn’t played the whole season. Still, would you have it any other way?

In real time, there were a million little moments of doubt and that gnawing curse feeling that kept creeping into every fan’s brain. Knowing the outcome in hindsight, it just makes it all the sweeter.