When competing in a large March Madness pool (think 20 contestants or more), there is a substantive difference between picking the teams you expect to win and picking a good bracket.
A good bracket zigs where others zag. A good bracket shuns convention (in moderation). At times, a good bracket defies otherwise good logic.
By its very nature, a high-entry bracket competition rewards high-risk behavior. The only way to win is to make picks others are less likely to make.
Now, that doesn't mean you pick Liberty to win it all (anyway, you can't now). Some risks, naturally, are too extreme to justify.
There is, however, a middle ground—subtle inflection points where one can make small departures from the pride without abandoning all hope of victory.