Troy Aikman
Selected first overall by the Cowboys in 1989, Troy Aikman was the biggest name in football in the 1990s, leading Dallas to eight play-off appearances and three Super Bowl wins, including a 52-17 rout of the Buffalo Bills in 1993. Despite his successes, Aikman also suffered from nagging back pain and no fewer than ten concussions throughout his career, and he made the tough choice to retire in 2001 at the age of 35, still fairly young for a quarterback. The Cowboys haven’t returned to the Super Bowl since.