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The Greatest Night in Chicago Sports History

For 30 years, Super Bowl XX has held the belt as the undisputed modern era Greatest Night in Chicago Sports History. With the Cubs playing tonight in Game 7 of the World Series, that title is at risk. OR MAYBE IT’S NOT.

Super Bowl XX

“Todd, as you can see, is standing in a hula skirt and a coconut bra. Todd, when was the last time you performed this ritual?”

“January 26, 1986, when the Bears won the Super Bowl.”

That date sounds best in Chris Farley’s voice. The reverence he places upon the numbers, particularly those consecutive sixes, always makes me smile. When the Bears carried Da Coach and Buddy off the field after a 46-10 deconstruction of the New England Patriots, that date became etched in the eternal, invisible plaque of Chicago sports achievements.

January 26, 1986.

The night the Bears won the Super Bowl.

I don’t mind calling it the greatest night in Chicago sports history.

That night has held the crown of Greatest Night In Chicago Sports History (GNICSH) for 30 years and 10 months. But tonight, the Cubs play in Game 7 of the World Series, and a win could put that game over the top of Super Bowl XX for any Bears fan who...

A. likes baseball more than football, or,

B. is too young to appreciate that magical night in January of 1986

Yesterday on Facebook, I broke down the Cubs-Sox divide and provided the fandom formula for, I would say, at least 80% of Chicago sports fans:

Bears + one baseball team + one United Center team.

The tension in the city for tonight’s Game 7 is as intense as anything I’ve ever seen. Objectively, I would argue that this game has the potential to be the greatest in the modern era, which I will call 1980 and onward.

By 1980, the major league mergers in basketball (NBA-ABA), football (NFL-AFL) and hockey (NHL-WHA) had all occurred, and MLB had divisions.

Six years later, on the aforementioned January 26, 1986, the Bears won the city’s only Super Bowl. Thirty years later, that team still rules the psyche of Chicago sports fans, united as we are around football.

The marks against SB XX for the record holder of GNICSH are meager: the game was all coronation and little competition. We didn’t simply know a win was coming. We knew a mollywomping of the ages was coming.

And it did.

Since then, we’ve seen nominees for each of our other major teams. In chronological order (and excluding the Wolves, since they were never #1 on the city’s hockey totem pole, even in the Dark Days):

POWER: 1991, Game 3 of the National Professional Soccer League championship

You weren’t expecting this one, were you? I can’t find all the details on this, but my recollection was that the Chicago Power soccer team won a championship in my childhood, and guess what — they did!

The Power knocked off the Dayton Dynamo in three games. According to, this was the first professional championship in the history of Chicago indoor soccer.

Doesn’t top Super Bowl XX because... the Power did not have even as great a following as the subsequent Chicago Fire, let alone the Bears. They’re probably just stoked to be on this list.

BULLS: June 14, 1998, Game 6 NBA Finals

Lots of potential nominees for the Bulls, but with apologies to Game 5 against L.A. and Game 6 against Phoenix, Game 6 in Utah takes the cake. We all knew the dynasty was coming to an end, so the game had our absolute attention (as well as the attention of the nation).

Then there was the in-game tension of not wanting to play a road Game 7, and the concern of how that might be avoided with a hobbled Scottie Pippen. Add to that the way the game played out, the historical significance, and the remarkable play of Michael Jordan (45 of the team’s 87 points, among other achievements), and this is a great nominee.

Doesn’t top Super Bowl XX because... nothing tops the Bears. As much as everyone loved the Jordan/Pippen Bulls, we still have plenty of fans in this city who prefer hockey to basketball. Also, since this was Game 6, it isn’t quite as intense as a one-night-only Super Bowl.

FIRE: October 25, 1998, MLS Cup

In its inaugural season and the third season of Major League Soccer, the Chicago Fire upset two-time defending champion D.C. United 2-0 at the Rose Bowl.

Doesn’t top Super Bowl XX because... the history and passion just aren’t there. Soccer fans were still getting accustomed to the MLS brand, and obviously were REALLY getting accustomed to the first-year Fire.

WHITE SOX: October 26, 2005, Game 4 World Series

Game for game, I’ll take the 2005 World Series over the 2016 World Series (at least so far). The Sox won Games 1 and 3 by two runs and Games 2 and 4 by one run, and became the first team in World Series history to win three straight World Series games in which they took the decisive lead in the 8th inning or beyond.

Game 4 was a thriller: the Sox won 1-0 on an 8th-inning RBI single by Jermaine Dye, scoring Willie Harris.

Doesn’t top Super Bowl XX because... the series was a sweep. Game 4 also fails the Super Bowl XX bar because only half the city pulls for the Sox, but even if we only had one baseball team that hadn’t won a World Series in 88 years, it’s hard to say that a Game 4 clincher is better than a single night of intensity.

BLACKHAWKS: June 9, 2010, Game 6 Stanley Cup Finals

For Hawks fans, this night probably tops Super Bowl XX, just as Game 4 of the ‘05 World Series tops it for Sox fans, I would guess. The Hawks broke a 49-year championship drought and did so in the most dramatic of fashion, with Patrick Kane scoring a game-winning overtime goal.

Doesn’t top Super Bowl XX because... of the same reasons listed above: Game 6 vs. one-night-only and Blackhawks vs. Bears. But hot damn, this was a beautiful night of Chicago sports.

SKY: September 3, 2014, Game 3 Eastern Conference Finals

The Sky finished the 2014 season 15-19 yet upset the Dream and the Fever to advance to their first WNBA championship in their then-9-year history. Guard Allie Quigley brought sharp shooting off the bench and led the Sky with 24 points in 26 minutes, helping the Sky secure a 13-point win.

Doesn’t top Super Bowl XX because... they didn’t win the championship, getting swept by the Phoenix Mercury. Simply reaching the championship series was a thrill for the Sky after their dominant 2013 ended in the first round. But you have to win a ring to compete with ‘85.

Right now, Game 6 of the 2016 NLCS is unquestionably the greatest Cubs night in the modern era. Advancing to the franchise’s first World Series in 71 years is nothing to sneeze at.

For Cubs fans who love baseball more than football, the combination of the dramatic series comeback, the anticipation of Game 7, the intense attention from the entire sports world, and the history at stake will push a Cubs World Series win over Super Bowl XX.

Ultimately, this list is stacked in the Bears’ favor, since the whole city roots for the same football team, with no other seasonal sport to detract attention. Like I said, objectively, and certainly nationally, a Cubs win tonight pushes that game ahead of Super Bowl XX due to a confluence of incredible factors.

Until then, long live the Shufflin’ Crew.


If the Cubs win the World Series tonight, which of the below games is the title belt holder for The Greatest Night in Chicago Sports History? Give us a top 3.

  1. Super Bowl XX
  2. Game 3, 1991 NPSL Championship
  3. Game 6, 1998 NBA Finals
  4. 1998 MLS Cup
  5. Game 4, 2005 World Series
  6. Game 6, 2010 Stanley Cup Finals
  7. Game 3, 2014 WNBA Eastern Conference Finals
  8. Game 7, 2016 World Series