In WWE, McMahon is a one-time European Champion and a one-time Hardcore Champion. He headlined his first pay-per-view event at the 1999 King of the Ring, and went on to become a world championship contender in the early 2000s, closing the 2000 Insurrextion and King of the Ring events in contention for the WWF Championship, and challenging for the WCW Championship at 2001's Unforgiven. He also participated in the main event of WrestleMania 2000, as a cornerman for Big Show.
On July 12, 2013, McMahon voluntarily stepped down as CEO of YOU On Demand and appointed Weikang Liu as his successor, while remaining the company's principal executive officer and Vice Chairman of the Board. He returned to WWE as an on-screen character in February 2016 where he went on to compete at WWE WrestleMania 32, co-in charge of Raw and eventually Commissioner of WWE SmackDown after the second WWE Brand Extension