As noted, Paul Heyman was a recent guest on Chael Sonnen’s You’re Welcome podcast and talked about a number of wrestling topics, including why Stone Cold versus Brock Lesnar won’t happen at Wrestlemania 32.
Heyman also talked to Sonnen about how he pitched CM Punk to WWE as the man to break the Undertaker’s “streak”, which could have happened at Wrestlemania 29 at MetLife Stadium in New Jersey. As far as how he brought it up, knowing Punk was close to wanting to quit the company. Heyman said he thought Punk beating Undertaker would be the only thing that could get Punk to stay in WWE, and if he a say in it Punk would’ve done it.
Heyman added to his initial comments, saying Punk might have stayed, but didn’t, and it worked out for his client Brock Lesnar the following year in New Orleans. He said he thought Punk getting the victory might mean he stayed a bit longer to “capitalize” on such a big win, but Punk left and the “stars were aligned for it” [the man to beat the streak] to be Brock.