My poor father. The guy is seriously up there in years (he had me at age 36), and he's been a Cubs fan all his life. Even worse, he's always been something of a South Sider, so it's not like he doesn't have any recourse.
But after the better part of a century following those "lovable losers", he got so fed up in recent years that he finally actually did something other than just complain every year -- something that was wholly unexpected. It was as if he got to the final realization that he will die never having seen the Cubs play in another World Series, let alone winning one. So he's been following White Sox games a lot more lately.
It may not seem like a lot to outsiders, but believe me when I tell you it's a "hell freezes over moment" and to sell all your shares of Microsoft.