It is possible that the most famous NFL team of the last 40 years and the most famous baseball team of the last 40 years both are from Chicago. The 1985 Bears … well, the 1985 Bears are so famous that just typing their name right there got you humming the “Super Bowl Shuffle,” or thinking about your old G.I. Joe Refrigerator Perry figurine, or both. They were recently selected as the greatest NFL team of all time. They’re as large a part of Chicago as the skyline. They’re Da Bears.But the 2016 Cubs may live on just as long. No franchise and its fanbase in American sports had suffered for as long or for as brutally as the Cubs had, from the Billy Goat to the ball through Leon Durham’s legs to poor Steve Bartman to Sammy Sosa’s bat to all of it. The Cubs winning the World Series for the first time in 108 years felt like an impossible cosmic event, like a wormhole opening in time, or someone inventing cold fusion. And yet it happened, and it happened in the most dramatic way imaginable, in the rain, in Cleveland, in extra innings, after Jason Heyward’s big speech, giving generations of Cubs fans a joyous release they never thought would come. Even this lifelong Cardinals fan cannot deny how moving it was to see Cubs fans writing the names on the Waveland Avenue wall of loved ones who never lived to see the day. It was the biggest story in sports this whole decade. It’s still amazing that it happened.But if there’s another thing that both those teams’ championships had in common, it’s that each was supposed to only be the beginning. The Bears were heavy favorites to win again in 1986, and the Cubs, famously, were thought to be building a dynasty. The 1985 and 2016 seasons were the launching pads, not the culminations. But those 1985 Bears never did win (or reach) another Super Bowl, something Bears players at the time still argue about. (Dan Hampton says the Bears would have won multiple titles with Jay Cutler as quarterback, which seems unlikely considering he was three years old at the time), and it has always felt like a disappointment: That team was too good not to have won more.And if they’re not careful: Those 2016 Cubs might just suffer the same fate.There is considerable turmoil on the North Side these days, perhaps more turmoil than a team currently holding a Wild Card spot and still well in the division race might deserve. But in context, you can understand why it all feels so perilous in Cubs land these days. Ever since they won that 2016 World Series, a title that was supposed to foretell so many more, it has gotten a little bit worse every single year:2017 -- The Cubs won 11 fewer games than they did in their championship season but still advanced to their third consecutive National League Championship Series, where they fell to the Dodgers, the team that appears to have usurped their NL dynasty label, in five games.2018 -- Despite leading the division for most of the season, the Cubs fell apart late and were caught from behind by the upstart Brewers, who tied them for the division lead on the final day of the season. The Cubs then lost a tiebreaker game for the division at home and then lost a heartbreaker in extra innings (again at home) in the Wild Card Game to Colorado.

https://www.mlb.com/news/2016-cubs-1985-bears-comparisons