Ok so being the least satisfying champion is dating the worst looking cheerleader. She may not make the cover of the calendar but she still looks great. In an expansion on my "Building a Perfect League Structure Post" I wanted to look at some of the least satisfying champions in major US Sports over the last 11 years.
2001 New England Patriots
Look at how they advanced in the playoffs. They beat the Oakland Raiders in a blizzard and on a referee's call. Oakland was by far the better team and just happened to be beaten by the elements and a rule that needed to be changed. Charles Woodson's sack on Brady was a fumble to anyone who was watching the game, but replay overturned the call. If the rule is as it should be, the Raiders advance and the Pats go home.
New England went on to upset the St.Louis Rams in the Super Bowl and claim the crown.
The second-worst champion of all time: the 2006 Cardinals, whose regular-season record of 83-78 gives them the lowest winning percentage ever for a World Series winner. They nearly blow a monster lead to the Astros down the stretch but got hot in the post season and won the World Series.
2007 LSU Tigers
They may have actually been the best team all year long. So why should they be on this list? They lost two games, and unprecedentedly ended up with a chance to play for the National Title anyways. Now to be fair both losses were in OT to Kentucky and Arkansas, both its disappointing to have a champion with so many blemishes on their resume.
2007-2008 New York Giants
The Giants are a wild card team that manages to win every road game in the playoffs including a bitterly cold game that would be Farve's last in Green Bay. They earn a rematch in the Super Bowl with a team that they lost to in week 17 at home, the undefeated New England Patriots. Sure it was great upset and full credit to the Giants, but it just feels wrong not crowning the Patriots champs when they are undefeated prior to the Super Bowl.
2010 San Francisco Giants
This team was made up of vagabonds to a degree and could barely hit. This may sound like sour grapes, but they beat Phils team that largely beat itself and were certainly not playing good baseball. They then beat the Rangers in the World Series which lacked pitching outside of Cliff Lee and C.J. Wilson. They got hot for the postseason but were slightly above average all season long.
Yes they won the Maui Invitational and the Big East Tournament, that was really impressive. However, they finished 9-9 in conference play and 9th in the Big East. The strongest team they beat in the NCAA tournament was probably Arizona. The NCAA tournament usually gives you a satisfying champion, but this year doesn't feel like it.
I'm sure I missed some but feel free to add to the list. I did not evaluate hockey because I don't know enough about it to do so.