Since Oct. 19, 2013, the Tigers, Lions, Pistons and Red Wings are a combined 5-25 in playoff games, with the Red Wings accounting for all five wins in first-round losses. So the question everyones been asking for years remains: Which team is closest to bringing a championship to Detroit? The only argument in favor of the Lions being the closest to winning a championship is the year-to-year unpredictability in the NFL. The former Red Wings legend has traded in his sweater for a suit and tie to bring Hockeytown back to glory. After floundering in the latter years of the Ken Holland era, Red Wings fans can feel optimistic about the direction of the franchise.