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Yes, the title of this post is a bit facetious; the best thing about March Madness is how unpredictable it tends to be. That doesn't mean I won't ever stop trying to to nail everything correctly. You can still toss your brackets into the ring by joining our tournament group on Yahoo! Sports if you get them in by the tip of the first game; the group is No. 53596 and the password is secspeed.
I'm going to talk a lot about likelihoods here, but I do realize that some likely things don't happen. By the same token, just because something doesn't happen, it doesn't mean it wasn't likely to happen all along. That's the beauty of March.
First Round Upsets
By synthesizing information from CBS, ESPN, the Harvard Sports Analysis Collective, and my own research, these are what I consider to be the most likely first round upsets at each seed line. The long shot upsets, like 16 over 1 or 15 over 2, are still far more likely not to happen, but if they do, here's what I'd guess for them. No specific upset has to happen, keep in mind; every upper seed from 1 through 8 has swept all four first round games at least twice.
16 over 1: UNC Asheville over Syracuse
15 over 2: Detroit over Kansas
14 over 3: Belmont over Georgetown
13 over 4: Ohio over Michigan
12 over 5: VCU over Wichita State
11 over 6: NC State over San Diego State
10 over 7: West Virginia over Gonzaga
This is not to say that these are the only upsets coming from these seeding lines, of course. I will mention that the 13-seeds all look pretty frisky this year, and also South Dakota State over Baylor wouldn't catch me by surprise.
Also, note that the most likely upsets at the 2, 3, 4, and 6 lines are all in the Midwest Region. Watch out with that one.
SOUTH REGION
First Round
1 Kentucky over 16 Western Kentucky: obviously
9 UConn over 8 Iowa State: when it doubt, take a team that went to the previous year's Final Four
12 VCU over 5 Wichita State: it's the most likely, and there's almost always a 12 that wins
4 Indiana over 13 New Mexico State: NMSU doesn't quite have enough, though IU is vulnerable away from home
6 UNLV over 11 Colorado: DO NOT BET ON THE PAC-12
3 Baylor over 13 South Dakota State: tourney newbies like SDSU almost never win their first games
7 Notre Dame over 10 Xavier: I like picking against Mike Brey, but this isn't a classic Xavier team
2 Duke over 15 Lehigh: a gimme in Greensboro
Second Round
1 Kentucky over 9 UConn: 'Cats are too much
4 Indiana over 12 VCU: this could easily go the other way, but 4s are usually good against 12s
3 Baylor over 6 UNLV: but it won't be easy
2 Duke over 7 Notre Dame: I can't see Brey beating K
Sweet 16
1 Kentucky over 4 Indiana: it's not in Assembly Hall, so we don't get a rerun
3 Baylor over 2 Duke: Perry Jones III is the difference
Elite Eight
1 Kentucky over 3 Baylor: John Calipari's best team isn't falling short of the Final Four
EAST REGION
First Round
1 Syracuse over 16 UNC Asheville: obviously
8 Kansas State over 9 Southern Miss: USM is way overseeded here
5 Vandy over 12 Harvard: the Commodores have finally broken through
4 Wisconsin over 13 Montana: Bo Ryan always wins first round games as a favorite
6 Cincinnati over 11 Texas: never pick Rick Barnes to outperform his seed
3 Florida State over 14 St. Bonaventure: as much as it pains me to say it
10 West Virginia over 7 Gonzaga: if it was in just about anywhere but Pittsburgh, I'd go Zags here
2 Ohio State over 15 Loyola (MD): no trouble here
Second Round
1 Syracuse over 8 Kansas State: but it won't be easy
5 Vanderbilt over 4 Wisconsin: Vandy's shooters carry the day
6 Cincinnati over 3 Florida State: FSU's awful offense will send it home early
2 Ohio State over 10 West Virginia: rough matchup sending OSU to a virtual WVU home game
Sweet 16
5 Vanderbilt over 1 Syracuse: no Fab, so Ezeli makes the difference
2 Ohio State over 6 Cincinnati: a huge game in Ohio, not so much for everyone else
Elite Eight
2 Ohio State over 5 Vanderbilt: Sullinger puts Ezeli in foul trouble, bad news for Vandy
MIDWEST REGION
First Round
1 UNC over 16 Vermont: obviously
9 Alabama over 8 Creighton: I believe in Anthony Grant
5 Temple over 12 USF: I'll take the team that can score over the one that can't
13 Ohio over 4 Michigan: let the chaos consume you
11 NC State over 6 San Diego State: feel the chaos wash over you
14 Belmont over 3 Georgetown: so much craziness going down in this bracket
10 Purdue over 7 St. Mary's: not such a big upset, actually
2 Kansas over 15 Detroit: this will be way closer than it should be, per Bill Self tradition
Second Round
1 UNC over 9 Alabama: closer than most think, but UNC doesn't lose tourney games in Greensboro
5 Temple over 13 Ohio: I almost went the other way on this
11 NC State over 14 Belmont: this one too
2 Kansas over 10 Purdue: Self is so much better against power conference teams
Sweet 16
1 UNC over 5 Temple: Williams over Dunphy every time
2 Kansas over 11 NC State: such a gift of a bracket for KU
Elite Eight
2 Kansas over 1 UNC: something about this UNC team just doesn't feel right
WEST REGION
First Round
1 Michigan State over 16 LIU-Brooklyn: obviously
8 Memphis over 9 Saint Louis: such a brutal 8-9 game, in a good way
5 New Mexico over 12 Long Beach State: UNM is better than you think
4 Louisville over 13 Davidson: hate this pick because I love the Davidson area; it's beautiful
6 Murray State over 11 Colorado State: CSU is overseeded and MSU is good
3 Marquette over 14 BYU: won't be easy for the Eagles
7 Florida over 10 Virginia: UVA's defense will be a tough test
2 Missouri over 15 Norfolk State: NSU is more play-in game material than 15 material
Second Round
1 Michigan State over 8 Memphis: but it will be close
5 New Mexico over 4 Louisville: Pitino's tournament troubles continue
6 Murray State over 3 Marquette: don't sleep on the Racers
2 Missouri over 7 Florida: in a battle of identical styles, pick the better team
Sweet 16
1 Michigan State over 5 New Mexico: give me Izzo over Alford every time
2 Missouri over 6 Murray State: the better team holds serve
Elite Eight
1 Michigan State over 2 Missouri: again, I trust Izzo more than anyone else
FINAL FOUR
1 Kentucky over 1 Michigan State: Kentucky's just a better team, and MSU arguably overachieved to get here
2 Ohio State over 2 Kansas: OSU's defense is the difference
CHAMPIONSHIP GAME
1 Kentucky over 2 Ohio State: Calipari finally gets his title