2005 - Nike Free Trail 5.0
Utilizing the then-somewhat-new Free sole technology on a trail shoe may have seemed counter-intuitive, but Nike has made a hell of a lot of money over the years by being exactly that. Not that the Free Trail 5.0 was some kind of monster at retail, but its very existence was what was important. Basketball shoes were becoming increasingly high-tech and complex (see the Air Jordan XX) and a basic trail running shoe with a perforated upper and decoupled sole represented a literal breath of fresh air. Compare the Free Trail 5.0 to many other sneakers of its era, and see which held up better.