#7 Shawn Michaels gets injured right before the Austin Era begins
In 1997, Shawn Michaels was notorious for his bad behavior backstage. He allegedly acted like a prima donna and at one point supposedly faked a knee injury. That injury derailed WWE’s plans at the time and was one of the many factors that led to the Montreal Screwjob.
A year later, this behavior would haunt Shawn as he got injured for real. At the 1998 Royal Rumble, he landed badly on a casket, injuring his back so badly he had to stop wrestling for four years. At the time, most people believed that Shawn would never wrestle again, and that his performance at WrestleMania XIV was his last.
But Shawn was a pioneer of the Attitude Era and his work with D-Generation X was critical to WWE becoming an interesting show. Yet, because of this poorly-timed injury, Shawn missed out on the Attitude Era. He only appeared on rare occasions, and never wrestled in any major capacity.
Because of that, fans never got to see HBK wrestling some of the Attitude Era’s biggest stars. And worse for him, Shawn likely missed out on some of the enormous paydays that came with those sold-out venues and record-breaking TV ratings. Had Shawn’s injury never occurred, there’s a good chance he’d have made more money by being a key player during WWE’s best ever period.
Superstars like The Rock, Triple H and Stone Cold made the most of Shawn's absence, cementing a legacy for themselves during the heydays of the attitude era.