It's a pretty random, probably uninteresting story but...
I originally was just a USA fan for the 2002 World Cup. That was about the only soccer I had ever watched until I got into smoking weed and playing FIFA a lot. I learned some of the teams and would usually play as Juventus because I liked the way the announcer said Trezeguet haha. I played as Chelsea sometimes too and the first time I met someone who actually watched soccer regularly was an American Liverpool fan from my college dorm. I said I was a Chelsea fan as a joke to piss him off, but had never even watched a league match. I went on vacation to Mexico that March, still an impressionable soccer fan, and finally saw a televised non-international match. It was Arsenal vs Juventus leg 2 in the knockout stages. Had Trezeguet scored a hattrick or had Juventus done anything worthwhile it may have been a different story, but it was a boring 0-0 disappointment. To make matters worse, Calciopoli relegated the team and left a sour taste in my mouth.
When the 2006 world cup came around, I was really excited to actually watch the non-pixelated players. The first player that really impressed me was Michael Essien against USA. When I heard he played for Chelsea it kind of sealed the deal. I would try to follow Chelsea. I'm not sure why but I didn't really follow the 06-07 season and only vaguely remember the FA Cup Final against Manchester United. I don't know what changed, maybe it was the availability on TV, but by 07-08 I suddenly was able to watch most of the Chelsea matches on TV and even managed to see some games in England when I went on a trip to London. Millwall v Luton, Charlton v Wolves (great match), and finally Chelsea v Boro. Going to Stamford Bridge was an amazing experience and I haven't really missed a game since.