What If: Bret Hart's 20 year WWE contract
In October of 1996 Bret Hart signed a 20 year contract with the WWE, obviously we all know what happened...Vince pulled out of the deal, screwed Bret, he left for WCW for huge money, Owen died, he was concussed and forced to retire, suffered a stroke, and eventually reconciled with vince about 15 years later. BUT!
What if none of that had played out that way?
October 1996, Bret signs the contract, and everything works out just fine. His contract would've just expired a few months ago. Where do you think Bret would be in his career at this point, how long do you think he would've continued wrestling for? What do you think his role would've been with WWE in his later years? Trainer, agent, manager, producer, Vince's right hand man? Would he have wrestled past his prime like Flair and Hogan?
It's a fun thing to speculate on.
I'd like to think he would've had a good run through the Attitude Era, similar to Undertaker but still would've had a back seat to Austin and Rock. Probably would've retired from active competition around 2003-5, eventually becoming an agent. I think he would've struggled with no longer wrestling, but without the health problems would've been a contributor for sure. Eventually ending up in a role similar to Pat Paterson's now, where he helps to book big matches, acts as an ambassador for the company, etc. Maybe would've become a GM at some point.