"You can't truly love a team until you've suffered with it." -- Bill Simmons, February 25, 2011
In chronological order:
1. October 6, 1993: MJ retires.
Sports is suffering, but we don't know that right away. For a while, we think sports might just be joy and grace and the Super Bowl Shuffle. Then something Happens, and we say, "Uh oh, what am I doing here?" The 1990 Game 7 loss to the Pistons that sent me running out of Donny Burba's house in tears was my first Horrible Moment, but the hurt was quelled by three straight championships and a sense of narrative, a collective instinct that three straight defeats to the Pistons were part of an Act II Low Point in a movie of Glorious Victory. By 1993, you wouldn't complain about the Bad Boy Pistons any more than you would complain about Apollo Creed at the end of Rocky II.
But MJ retiring on October 6, 1993? That was a blow. That was one we didn't see coming. And even though it led to one of my favorite seasons (the 1994 Bulls), Michael Jordan's first retirement was, as I later wrote, "your girlfriend dumping you on Valentine's Day." The first sign of my first twelve years that staking your happiness on professional sports was a futile life...
2. Steve McMichael joins the Packers
...and yet, as much as Jordan's '93 retirement was a destructive force in my young fandom, I was in no way prepared for Mongo McMichael to join the Packers. At least MJ was playing baseball; it's not as if he was on the Knicks. But a member of the '85 Bears willingly suiting up in the green-and-gold? A massive loss-of-innocence moment for young Sports Fan Jack -- here he was introduced to The Business.
3. The 1999 Bulls.
Nobody believed in the '94 Bulls, and they won 55 games and a playoff series. So when Michael and Scottie and Dennis and Phil (and Luc and Kerr and Buechler and Burrell) rode into the moonlight, I thought, "Not to worry. Kukoc, Harper, Brent Barry, a 50-game season... we'll compete for the eighth spot at least!" In the words of Charlie Murphy, "Wrong! Wrong!"
The '99 Bulls finished 13-37, the launch pad to a six season stretch in which Your World Champion Chicago Bulls! won an average of 21 games per season, and regaled us with the athletic feats and heroism Kornel David, Cory Carr, Corey Benjamin, Andrew Lang, Mark Bryant, and Charles Jones.
4. Game 7 of the 2003 NLCS.
Game 6, AKA The Bartman Game, is remembered today as The Worst Moment in Chicago Cubs History. But Game 7 was infinitely more deflating. At the time, Game 6 was just some bizarre game that happened, and not to worry, Woody's pitching tomorrow. It was like getting black-out blitzed the night before your wedding, and waking up with only a tiny headache. "That wasn't so bad," you think as you put on your tux. Then you arrive at the chapel to learn from your fiance that Mindy the cocktail waitress answered your cell at 6 AM this morning, and whadya know, the wedding is off.
5. Quarters 2 through 4 of Super Bowl XLI.
The 1992 Bears lost six straight games and eight of their last nine, and the 2001 and 2005 Bears dropped home playoff games after division championships, and it all sucked in different ways. But nothing tops losing a bad-weather Super Bowl to a bunch of carpet-treading pansies like the Indianapolis Colts. Good golly... don't get me started...
6. 2008, Cubs v. Dodgers... the death knell...
The 2008 Cubs's failure to win even one bloomin' playoff game after bagging 97 regular season wins was the final strike against my Cubs fandom. Let's not even dissect this one. I'll just tell you that my post-'08 Cubs column was written in a state of near catatonia, and that I have not watched baseball since Soriano struck out.