Yes, this is
way too ASB.

And localist.
But anyways, here's your challenge. Have the Chicago Cubs win a World Series after 1980. Bonus points for the closer it is to the present-day.
I expect 'no Bartman' to be an answer here.
After '80, the best bet would have been 1984. They had San Diego down 2-0 in a best-of-five series; one win in the last three games would have been enough to gain the Series. Beating the Tigers (ironically, their opponent in 1945, the last time they made it) would probably be feasible, considering San Diego took the Series to seven games.
I realize it's before the starting point, but 1969 would also have been a good possibility. Had the Mets not gotten white-hot or the Cubs stalled, the Cubs could have made the Series then. I don't think they'd have won, however, going against that pitching- and hitting-rich buzzsaw of the Orioles of the day. Frank Robinson and Boog Powell would have had fun putting balls onto Waveland or Sheffield Avenues in that Series.