I wasn’t even alive during the Chicago Bears historic 1985 season. But I’m old enough to lie and say I remember watching Michael Jordan win his rings. (If I’m being honest, I was only six and was far more concerned with the Power Rangers.)
Luckily, I distinctly remember the White Sox winning the World Series back in 2005; the sports page from the Chicago Sun-Times is still on my bookshelf. And, if I’m being even more honest, I only got into hockey during the Stanley Cup finals this last year so I only got to enjoy 5% of the Blackhawks dynasty.
Even with the previously mentioned championships, being a Chicago sports fan is possibly one of the most difficult things in the sports world.