I was working for a sports marketing company in 1998—FANSOnly (not to be confused with the modern-day ONLYFans), which ran HurricaneSports and a bunch of other official websites for universities.
Boss was a huge UCLA fan and we'd been jawing all season about the Canes and Bruins playing; the game postponed to December and taking place a week after Miami got throttled 66-13 at Syracuse.
Big lunch meeting with entire office, he was all over me and I told him I'd bet him whatever he wanted—Miami was going to take out undefeated UCLA in the Orange Bowl.
Can't even remember the bet at this point; money, some bonus days off, etc.
I just recall going into work that Saturday after the game (he didn't work weekends) and just wrecking his computer with Miami / UCLA Getty Images—saving to desktop and anywhere else I could on his PC. Set his mail up to play the UM fight song every time new mail came in. Whatever way I could embed nonsense from that upset onto his machine, I did—and it was there for days. He eventually had the tech guy swap out a new machine for him.
Months later, wrote a piece predicting that Miami would take out No. 9 Ohio State in the Kickoff Classic.
Again, hardly colossal upsets in the grand scheme of things—but one was in front of my entire company a few months into my first job and the second was a national article and bet against the office Ohio State puke, who had to wear my #21 James Jackson jersey all day the Monday after.
Lastly, we ALL knew Miami would roll Nebraska in Pasadena, but I was pounding Crown at a multi-hour tailgate and told them the Canes would be up 35-0 at the half and they had zero shot—a men against the boys beatdown was on deck.
I was wrong, Canes were only up 34-0.
My guy 
