#3 Stephanie McMahon
One of the two McMahon's that Paul Heyman reportedly clashed with heavily during Heyman's first run in the company between 2001 and 2006 is Stephanie McMahon.
Heyman and Stephanie were a part of the writing team in WWE, and the two apparently did not see eye-to-eye on various issues. Paul Heyman admitted in an interview in 2008 that he and Stephanie had disagreements on various issues:
"They weren’t rumours, Stephanie and I clashed heavily through most of my tenure in WWE. And I don’t think it should be a surprise that we did. I came into WWE just as Stephanie was taking over the writing team."
Jim Ross also spoke about this rivalry between Heyman and Stephanie in the mid-2000s, stating that the two had "a lot of philosophical differences".
"I know that she and Heyman had a lot of philosophical differences. And I’m sure that Paul got close to the edge on how far to take the argument before he backed away. Because he just was hellbent on getting his way. He was very defiant. Not that she wasn’t, but she had the right last name and he didn’t."
But, Paul Heyman revealed that Stephanie tried her best to keep him in WWE, offering him a role as a writer in WWE's developmental promotion, and was supportive. He also praised Stephanie for being a hard worker with a great work ethic.