Odds of Winning: 20-1
Keep your fingers crossed -- if he wins, he'll probably spread the wealth by taking everyone out to Chi-Chi's for lunch!
THE GUY WHO DOESN'T PICK ANY UPSETS
This guy will talk at length about how he liked the grittiness Kansas showed in the Big 12 tournament even though it's obvious that he just put a checkmark next to their name because they have a lower seed than their opponent. The really aggravating thing about this conservative approach is that, while it would never fly in a legit NCAA pool that weights for upsets, in a bush league office pool that just tallies the number of wins, this guy will do well more often than not. Even more annoying is how hard it is to find a box of live cobras to FedEx him.
Odds of Winning: 10-1
"Tupac didn't play it safe either," you'll tell yourself while picking Western Kentucky to make it to the finals, and again when they lose in the first round. Sadly, thinking of yourself as the Tupac of your NCAA Office Pool will not make this guy's victory sting any less.