In college, I had a couple of friends that were from Chicago. They loved their Cubbies and their Old Style. Every spring Tony (from Cicero) would say, 'I think this may be their year'. We always laughed about it but I admired the loyalty of those guys. I saw Tony for the first time in over 30 years just a couple months ago. He was still on the bandwagon, of course, though it's obviously easier these days. He never gave up.
My sister moved to Chicago almost 30 years ago, and her entire family became Cubs fans. BIL and nieces went to a couple spring training camps, even when they sucked -- there was always the early-year optimism. But, they are true fans. They didn't flip when the Sox were good -- they stuck it out and suffered.
I just happened to be in Chicago the weekend they were playing in the Series. That town was electric, and all Cubbies. I didn't see a White Sox ANYTHING until the day we left. It was a great atmosphere to be around -- everybody was upbeat and ready for them to win, even after the losses. The ONE person that I saw that was a 'negative Nancy' was the guy working the desk at our hotel when we checked out. He said they always choke and it was gonna happen again. What a sad guy.
One of the jerseys I saw the most around Chicago was #18, Ben Zobrist's. He was an extremely well-liked player in his one year, last year, with the Royals. Just a good guy and a lot of us Royals fans hated to see him go. Me, I kinda liked that he went to the Cubs, if he had to go somewhere. Just after the Series last year his wife had a baby girl -- Blaise Royal Zobrist So, now he's sporting two WS rings and got MVP to boot.
So, I've liked the Cubs for a long time, but I won't exaggerate it by claiming to be a fan. I leave that to the real fans, and they're some of the best.