14 Wrestlers Who Should Probably Regret Leaving WWE

3. Ricky "The Dragon" Steamboat

Over the past 20 years, Ricky Steamboat has had a tumultuous on and off relationship with WWE. In 1988, only a year after his epic encounter with Randy Savage at WrestleMania 3, Ricky Steamboat retired from in-ring competition and left WWE. The story is that Steamboat requested some time off from WWE competition shortly after WrestleMania 3 to spend time with his wife and newborn son. This didn't sit well with Vince McMahon and other higher ups in WWE and he was forced to drop the Intercontinental Championship to The Honky Tonk Man. After a successful run in the NWA, Steamboat once again returned to WWE for another short-lived run. This time, Steamboat allegedly quit because he was set to lose a squash match to The Undertaker on an episode of "Superstars" a few weeks before Undertaker was set to win the WWE Championship from Hulk Hogan. At this point, Steamboat headed back to WCW for another successful run, albeit not achieving the World Championship caliber success in his previous stint. Unfortunately, Steamboat suffered a career-ending back injury in a match against Stunning Steve Austin and was fired shortly thereafter via FedEx package by Eric Bischoff. While it is unlikely that Ricky Steamboat has any real regret about leaving WWE on two separate occasions, one has to wonder what path his career had taken if he didn't leave in both instances.