Either way, I dont think Shawn would have wrestled for much longer because he was already starting to carry alot of injuries with him even before the casket match with Taker. His knees and his back had been bothering him for some time, The casket match just did it in for him.
Had he not injured his back against Taker, we might have seen him in a dynamite kid situation where he continued to work / use drugs even though he had crippling pain. I compare dynamite and HBK in 98 because they were both at that physical point where they needed to take time off, or stop wrestling if they couldn't heal. HBK left the business to rest and eventually have surgery, and Dynamite wrestled for like 5 more years on a blown back.
Had Shawn continued to wrestle past 1998, he may have made it a year or two longer, but like others have pointed out, his nagging injuries and drug habit was an accident waiting to happen. HBK also had a great deal of bitterness for a while towards the business during his first retirement, that motivated him greatly in 2002 to return, so he could come back and do things "The right way" as he said in his book. If Shawn wouldn't have retired in 98, he would have worked another few years and got out of the business totally wasted, physically and because of drugs. If he didn't die, i dont think he would have ever returned to active wrestling again.
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