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Jake Roberts
Jake Roberts was someone who sat and smiled at the epitome of in ring psychology and gimmick brilliance. He had enough talent in him to become a class act in the business but a lot of struggle with his personal demons derailed Jake’s career. The problems he had during the late 90s are well documented and it should have been the right time for Jake to hang up his boots.
Jake however went on to wrestle till 2011 where he officially announced his retirement. Jake was then inducted into the WWE Hall of Fame but that did not keep him away from the ring. He made a lot of independent appearances afterwards and though they seemed solid, it was never the right way to follow up the WWE Hall of Fame ceremony which gave him a fitting farewell.
Bret Hart
Bret Hart left WWE as a big baby face thanks to the Montreal Screwjob. The legacy he left back in WWE painted him as a legend that got screwed over. After the Montreal incident, Bret went on to have a forgettable run in WCW at the end of which, he retired.
Most of the wrestling fans out there completely ignored the time he spent in WCW and always saw him as the great wrestler he was thanks to everything he did in WWE. It would have stayed the same if he had not come out of retirement for WrestleMania 26.
More than a decade after the Montreal Screwjob, Bret had his first match in WWE and that too against Vince McMahon. Both the superstars were in no condition whatsoever to give a wrestling clinic and it ended up being an overbooked mess that no one wanted to remember. Bret later went on to win the United States Championship as well by beating Miz, but all these matches tagged Bret as a superstar who should not have returned from retirement.
