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The last time a guard won the Defensive Player of the Year award was over 15 years ago when "The Glove," Gary Payton, reigned supreme on the the court. Before then, Michael Jordan (eight years earlier) grabbed the award, and Alvin Robertson snagged it two years prior.
Milwaukee's Sidney Moncrief repeated winning the award in its first two years of existence, but the emergence of extremely athletic, defensive centers has made it very difficult for a guard to contend, let alone win.
It would take A LOT of hard work, but Tony Allen could be the one to break the dry spell of guards in the running for the defensive accolade. A very athletic, defense-first shooting guard for the Memphis Grizzlies, Allen is a nightmare for slashers and shooters, combining his swift feet with his quick hands and incredible awareness.
He's recognized around the league for his sticky defense, but Allen will have to bring his steals per game average way above 1.8 if he wants to be in the running next season.