Odds of Winning: 10-1
"Tupac didn't play it safe either," you'll tell this guy as you laugh dismissively at his womanly bracket, and again when he finishes in the top three in your office. Sadly, thinking of yourself as the Tupac of your NCAA office pool will not make his success sting any less.
Your boss's daughter burst onto the scene in 2006, when she correctly picked Florida and UCLA to go to the finals because "that's where Mickey Mouse lives," and Georgetown because her imaginary friend is named George. Before the second round is underway, you'll be cursing her under your breath while the rest of the people in your office have the good sense to pretend like she hasn't entered her awkward phase.
Odds of Winning: 45-1
It's a bad year for her as the Universities of both Disney Land and Disney World both had down years, and her third favorite UNC (the pretty light blue team) isn't even in the tournament. She could make some noise in the later rounds if three seed Georgetown goes deep, while you quietly point out to no one in particular that she's probably too old to have an imaginary friend.