Bret Hart vs Vince McMahon should have been the easiest thing in the world to book. Bret finally returns to WWE after over 12 years away from the company in the wake of the Montreal Screwjob, tries to make amends, Vince ambushes him, they cut promos on each other for weeks and Vince gets destroyed at WrestleMania.
It started well enough. It started the way you'd hope. Bret showed up to host Monday Night Raw, tried to make amends and Vince cheap-shotted him with a kick to the groin. It kept going fairly well for a few weeks, with other heated confrontations—Bret flipping out when Vince said he'd never induct Stu Hart into the WWE Hall of Fame, Vince agreeing to a match at WrestleMania 26 and chickening out when Bret attacked him, etc.
Then the car accident happened.
Car accidents are poison for good storylines. In this case, Bret announced that with Vince refusing to agree to the match, he was best off just cutting his losses and leaving, only to be hit in the leg by a car. In light of this new development, Vince decided he might as well agree to the match since Bret was injured.
With Steve Austin having authority the night of the contract signing as Raw guest host, he announced that Stu Hart would in fact go into the Hall of Fame and that the WrestleMania match would be no holds barred. After Vince signed the contract, Bret revealed that the accident had been staged with John Cena's stunt coordinator friends (yup) to get him to agree to the match and then hit him with his cast.
It was a cute payoff to the accident, but this was a feud that needed to be boiled down to the bare essentials. Still, the match itself should have been simple enough to get right, but it didn't turn out that way.
Nobody had any illusions about the match being good. Bret retired in 2000 after suffering a series of concussions in a few weeks, and subsequently had a stroke a few years later. He made a remarkable recovery, but had no business having a regular match. Going into WrestleMania, it didn't seem to matter since he just needed to beat up Vince.
However, Lloyd's of London felt that no matter the circumstances, the match was a violation of the terms of his permanent disability insurance settlement. Vince wouldn't be able to do anything to Bret—He couldn't even rake his eyes or put him in holds. Again, you'd expect this not to matter too much since ideally Bret could just punch Vince and put him in the sharpshooter.
I don't know if they felt that wouldn't give the fans' their money's worth or what, but the match went on for eleven minutes even though one wrestler couldn't be touched. It felt interminable, with Bret methodically beating Vince up the whole time. What should have been a great moment ended up being really depressing.