It wasn't supposed to be this way for Chicago Cubs fans after they won it all in 2016

Instead of marking the start of a dynasty in Wrigleyville, things went quickly downhill following that unforgettable season and show no signs of turning around soon.
Los Angeles Dodgers v Chicago Cubs
Los Angeles Dodgers v Chicago Cubs / Jonathan Daniel/GettyImages
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Let's put away deep analytical dives into the Cubs for a second and just look at the state of the team purely from a fan perspective. It wasn't supposed to be this way.

This isn't just about the struggles of the 2024 team. This extends to an entire era of baseball Cubs fans have lived in since the 108-year drought ended in 2016. Where we were, the changes in expectations, and how we ended up here. There are many lessons and realities to take away from how the eight years since that World Series victory have played out.

On that November night, the joy of finally winning it all turned into an even greater outlook for the Cubs franchise. There was the feeling that it was only the beginning of what could be a long-lasting run at glory. The term "dynasty" was thrown around, and with a young budding core and a new state-of-the-art franchise infrastructure, it seemed reasonable to believe they could make that sort of a run. The thoughts of annual postseason action at Wrigley Field over the next 5+ years, especially with the new renovations in and around the park, were exciting—no more "Lovable Losers" or futility. Maybe similar to what the Blackhawks did from 2009-2017; a team that, like the Cubs, was once stuck in the Stone Age and then joined the 21st century resulting in multiple championships around their cornerstone players.

Fans learned the hard way there are no guarantees in sports as the window just never seemed to fully materialize the way we'd anticipated. Injuries, decline in performance, prospects that didn't pan out, trades/free agent moves that didn't work. We can break it down for the 10 millionth time but we won't. The Cubs are now seven years separated from their last playoff win and are likely going to be four years past their last playoff berth - a series that saw one total Cub run scored and zero fans in attendance due to the COVID-19 pandemic. The last time fans packed Wrigley for October baseball was the wild card game loss to the Rockies in 2018.

The run the Cubs made from 2015-2018 was very special, but the way it faded so fast after winning in 2016 was just not how the rest of the era was envisioned. There was the opportunity for Jed Hoyer to rebuild the team after things fell apart and bring it back to relevancy, but so far, he's come up short.

Cubs fans never thought they'd have to endure so much losing so soon

One of the most disappointing seasons in recent memory has fans at their boiling point. It feels like the days of old are back and they are back way too soon. What was hopefully going to be the 2010s Blackhawks became a bit more reminiscent of the 1985 Bears, a championship team that had much promise ahead but just did not get back to title glory again. (And they're still waiting after nearly 40 years).

Heck, if the Hoyer rebuild worked and the Cubs looked good now it would be much easier to accept how the last era ended and move on. A relatively short lull, followed by returning to relevancy is still better than another potential losing season this year (three of their last four seasons will be losing seasons if they finish 2024 below .500)

Could it be worse? Of course. The Cubs could have lost Game 7 and they would be on year 116. A strong farm system could at least give fans hope in the coming years things can get better again, but right now it's a tough pill to swallow. Wrigley Field is still packed an lively despite the last-place team, and the fans deserve a fun product after paying 108 years worth of dues.

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