Kate Austen = Vince Lombardi Trophy: She is the ultimate prize for Jack and Sawyer. They have openly confessed that they love her. Hell, Jack is trying to blow up the Island because he blew his chances with her.
Juliet Burke = National Invitational Tournament (NIT): She was always second fiddle, just like the NIT. When Jack couldn't have Kate, he kissed Juliet.
When Kate left the Island, Sawyer fell in love with Juliet. When Kate returned, Sawyer, more or less, forgot who Juliet was.
Hugo "Hurley" Reyes = Albert Haynesworth: Hurley won the lottery for millions of dollars and it brought him nothing but back luck.
He believes he's cursed.
Albert Haynesworth hit the proverbial lottery when the Redskins gave him one the biggest contract in the history of the NFL.
It has brought him, and everything in his path, nothing but pain and sorrow. He's been injured, his team had a terrible season, and the team he left, the Titans, went from the best record in the AFC to missing the playoffs this season.
Oh, and they are both terribly overweight.
Charles Widmore = George Steinbrenner: Widmore is the former leader of the "Others". He is uber wealthy and tries his darnedest to remain relevant. Despite loving the Island, he is willing to sacrifice it, to get what he wants.
Steinbrenner used to be the leader of the Yanks, who also has too much money on his hands. He loves baseball, but some look at the amount of money he spends on his team as a disgrace to the game.
Sayid Jarrah = Pac Man Jones: Both have been given second and third chances to change their path, but still, somehow, fall back into their bad habits; Sayid being a torturer/assassin, and Pac Man trying his hardest to make it rain.
Shannon = Anna Kournikova: Both are so hot and neither lived up to their potential.
Vincent the dog = Vinny Testeverde: They are there when you need them. How many times will Vinny come back as a serviceable backup?
Rose & Bernard = John & Nell Wooden: Rose and Bernard want nothing more than to be together, and they don't care who else is around.
This is reminiscent of the love that John & Nell Wooden shared. When UCLA wanted to name the court after him, he insisted that her name be included.
Jin & Sun = Charlie Weiss & Brady Quinn: They were much better together. Apart, they are very forgettable.
Daniel Faraday = Bill Belichick: Both are sneaky geniuses. You never know what they are thinking...and they both have horrible style.
Miles Straume = Mike Tyson: Miles can hear dead people. Tell me, honestly, would you be surprised if Mike Tyson said he could hear dead people as well?