Year: 1985
Sneaker: Nike Air Jordan 1

Hindsight is wonderful. Of course Michael Jordan over Sam Bowie is a no-brainer now. But back in 1984 it clearly wasn't, seeing that the Portland Trail Blazers went the other way. Likewise, when Nike inked Jordan to a sneaker contract and made him the focus of more or less their entire basketball marketing push, it was a tremendous risk. Sure, basketball guru Sonny Vaccaro insisted it was the right move, but this was a 22-year-old rookie joining a team that had gone 27-55 the year before. So much could go wrong. Needless to say, it didn't.