WWE Executive Chairman Vince McMahon was willing to take a hands-off approach when it came to the 2005 feud between Shawn Michaels and Kurt Angle.

The feud between the two began at that year's Royal Rumble, when Angle was eliminated from the Rumble match by Michaels, and re-entered the ring to return the favor. Angle would explain that his issues with the Heart Break Kid dated almost a decade ago, as after winning a gold medal in the Atlanta 1996 Olympic Games, Kurt heard people talk about Michaels' Iron-Man match victory over Bret Hart at WrestleMania 12.

With the two men attacking each other on both Raw and SmackDown, fans were eager to see the dream match between two of the greatest ever. Speaking on his podcast, Angle revealed that Vince Mcmahon, in a rare sign of casualness, let the two choose their own winner at WrestleMania 21.

”Listen, there’s no doubt in my mind that if Shawn was going to lose at WrestleMania to me, I’m gonna have to pay it back. There’s no doubt about it. Yes, that’s how it works. And I don’t blame him. I was willing to do that, because he did me a huge favour.

"Actually, Vince didn’t have a winner for WrestleMania. He had us work it out between ourselves. And Shawn said, Listen, I’ll put you over. Because I know, this is what he said, and I totally forgot this. He said, You know what, you’re gonna end up doing a programme with Cena afterward, and what you need is a good win right now."

Angle's feud with Cena would see the Olympian challenge for the WWE Championship multiple times, but would never dethrone Big Match John.

WrestleMania 21 saw Angle be chosen as the winner of the match, in an all-time classic in the careers of both men. Later that year, Michaels would get his win back at Vengeance. On the October 3, 2005, WWE RAW Homecoming (as the show was returning to the USA Network,) the two wrestled to a 2-2 tie in an Iron-Man match. Despite Michaels challenging Kurt to overtime, Angle refused. The feud would end for good inside the Elimination Chamber at New Year's Revolution 2006, where Angle was eliminated by Michaels.