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2nd Worst: Losing to the Cubs in the 2015 NLDS
This one, from a baseball perspective, probably stung the most amongst the Cardinals fanbase. As mentioned before, this seemed to signify the turn of the tide of the NL Central. The young highflying Cubs stepped on the throats of the Redbirds in this series and put them in the rearview mirror for the next three years.
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Watching the Cubs beat the Cardinals in 2015 and then, in turn, watching them continue their dominance and end up winning the 2016 World Series in dramatic fashion made some Cardinals fans want to claw their eyes out. Really the only good thing that came from the series was watching Tommy Pham take Jon Lester way deep basically into Ballpark Village.
The Cubs gave us a little taste of our own medicine and boy was it painful.
After being the big brother bully to the Cubs the past century, watching them come into Busch Stadium and take the series from us after a 100 win season was shocking and a gut check for sure. But thankfully the Cardinals were able to regain the NL Central title in 2019 after three long years of no postseason in St. Louis and we all pray that we never have to watch Theo Epstein hold up that World Series trophy ever again.