Your boss views the NCAA office pool as an opportunity to establish some common ground with his staff, and dole out some good-natured ribbing.
"Hey Doug, what happened to your Kentucky Wildcats this year?"
"Sure Dave, like I'm going to listen to a retard who has Pitt going to the Final Four."
"Michigan? Michigan Irene? They're not even in the fucking tournament! See, this is why women aren't allowed talk at meetings."
It's important to keep in mind that your boss didn't come to lord over you by shying away from competition, so it's best to keep the reciprocal chiding friendly and light. Avoid wild accusations that he's at the center of a vast Masonic game-fixing conspiracy. Even though he so obviously is.
Odds of Winning: 20-1
Look on the bright side-- when he wins, there's always a chance he'll 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 check next to their name because they were a one seed. The really aggravating thing about this dickless approach is that, while it would never fly in a legit NCAA pool that weights for upsets, it works most of the time in a bush league office pool. 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 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
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.
THE GUY WHO'S WINNING IN HIS OTHER POOL
This guy pinned his bracket's hopes on the only one seed that lost before the Sweet 16. Rather than just keeping his mouth shut while everyone else talks about their still-alive bracket, he'll try to convince everyone that he's picked every single game correctly in his dad's office pool. "See this was just my upset bracket. I wasn't even trying on this one. In my dad's office pool I haven't lost a single game in the last three years. Whenever I drop by the old man's office, they call me 'the kid' and carry me around on their shoulders." In all likelihood, this guy's father doesn't love him or is dead. Either way, it's probably best not to call him on it until you're out with your boss and co-workers at Chi-Chi's. You're going to want everyone to hear that.
Odds of Winning: 60-1
Despite the fact that he felt like he needed to fabricate an elaborate story to cover up his failure, he will still probably do better than you.
THE GUY WHO PICKS DUKE EVERY YEAR
If you have a Duke grad in your office, you can rest assured that he's picking his alma mater to win the championship. But there's also another type of guy who picks Duke every year, usually older, and almost definitely afraid of black people. To determine which sort of Duke apologist you have on your hands, ask him why he's picking the Blue Devils. The Duke grad will talk about the team in the first-person plural, as in "our freshman are tremendously resilient," whereas the guy who's scared of black people will say he thinks that Duke's token white point guard "has a good head on his shoulders" and point out that "they might not have the most talent, but I like the way they play together as a team."
Odds of Winning: 70-1
Duke's a one seed so he's basically got as good a shot as they do. For the most part, this guy lost his ability to beat anyone (except for you) when Christian Laettner left for the pros.
THE BRACKET PRO
This guy has done his research--too much in fact. When you tell him you like Georgetown, he'll go on a Good Will Hunting-style rant: "Sure you think Georgetown's gonna win. You read Dick Vitale and Bill Simmons. You'll think that 'till you read Bilas' article on the Hoyas' susceptibility in transition. The sad thing is at the end of this tournament, you're going to realize that you spent $15 on an education from ESPN Insider that you could have gotten by swallowing a handful of Ritalin and watching your Xbox simulate all 65 games before hand." He'll be dying to explain every single one of his picks in great detail, both before the tournament starts and after all of his upsets don't happen and he's mathematically eliminated by the third round.
Odds of Winning: 101-1
The Bracket Pro is the only person in your office who might do worse than you. Good. But, he's also the only person in your office pool who you should take seriously when he says he's thinking about "doing something crazy if Marquette doesn't pull this one out."