I've never really been a fan (in the fanatic sense of the word) of a championship team at any level. I focus on teams because it's something completely different to be a fan of a particular player--I'm a fan of Tiger Woods, for example, and I was a fan of both Andre Agassi and John McEnroe in their primes. The individual performer is easier for me to relate to than the team.
Part of this comes, no doubt, from being exposed to hapless teams from a very early age. I went to my first baseball games when I was in first grade (I think). We got free tickets to see the Houston Astros, and I really don't remember much other than the scoreboard lighting up when someone--I don't even know which team, much less the player--hit a home run. The Astros weren't very good at the time--this was the mid-70's--and I never really developed an affinity for them because I was too young to understand the sport, especially since my parents weren't the kind to let me play little league.
My first team experience was the New Orleans Saints; I moved to Louisiana when I was seven, just before starting the second grade, and the Saints were bad--as they had been and as they would remain for many years afterward. They were also the only game in town, mostly, and the other games in town were also bad. The New Orleans Jazz were creeping slowly toward respectability, led by Pistol Pete Maravich (probably the least-known all-time-great basketball player in history), but they still lost more than they won. There was no baseball team, and New Orleans's contribution to college sports was Tulane University, not exactly a hotbed of excellence.
I felt an affinity for the Saints. They came into the league the year before I was born, and seemed as hapless on the field as I did on the playground before school and during recess. I was not an athletic child--glasses in kindergarten and asthma will do that to you--but I loved playing all the same, even though it meant trips to the optician and learning how to repair broken glasses with tape and paperclips. Steve Bartkowsi's Hail Mary against the Saints to complete an incredible comeback still stings thirty years later. I turned 12 the year the Saints went 1-15 one year after going 8-8, knocking on the door of what was their elusive first winning season. They beat the Jets. I remember being nervous before the Saints played the expansion Tampa Bay Buccaneers, who were 0-26 at the time going back over two seasons, desperately hoping the Saints wouldn't be their first victim. I took no solace in the fact that the Bucs would win their next game, and would then make the playoffs the following year.
The story of Saints futility is a long one--thirty years before even having a winning season, and only 8 of 41 winning seasons total. Only three head coaches in the team's history have winning records: Jim Mora, who led the team to their first continued success; Jim Haslett, who led them to their first playoff victory; and Sean Payton, who has them currently at or near the top of most power rankings. Other teams have had really bad eras--the Cardinals had a really crappy couple of decades recently--but no team has ever defined futility over the long haul like the Saints.
So it's no surprise, given my love for the Saints, that when I started hunting for a baseball team to adopt (since we had no New Orleans team) that I would gravitate toward one which felt familiar. I shifted from team to team as a kid, mainly following players--the Dodgers of Steve Garvey and Ron Cey, the Cardinals of Willie McGee and Tommy Herr, George Brett's Royals (I still have the glove I got after Brett's .390 season)--but didn't really follow a team until I was an adult. I'm a Cubs fan.
When the Red Sox ended their run of World Series futility a few years ago, lots of commentators suggested that Boston fans would finally have to give up their fetishization of losing, because they had nothing to complain about. That's not going to happen--Sox fans will continue to internalize their status as losers until the Sox have won as many World Series as the hated Yankees, which will probably happen about the time the head of Richard Nixon wins the presidency of Earth.
Cubs fans are now alone in their celebration of mediocrity, at least in baseball. I don't celebrate it, though. I would love to see the Cubs win the Series, just as I am hoping against all hope that the Saints pull it off this year. And I wouldn't feel like a part of me is missing if that happens. I don't root for also-rans because I'm celebrating crappiness--I root for them because they're all I know how to root for. The Saints trained me to have hope just so it could be dashed. I don't know any other way to react as a fan.