Matt Riddle Picks Vince McMahon As Best Boss Over Triple H

Matt Riddle has weighed in on who gave him the best experience as a boss during his wrestling and MMA career, and the answer wasn’t Triple H, Shawn Michaels or Dana White — it was Vince McMahon.

Appearing on the That Sweet Pop podcast, Riddle was asked to rank the authority figures he has worked under, a list that included UFC president Dana White, former WWE COO Triple H, WWE Hall of Famer Shawn Michaels and McMahon himself. Riddle didn’t hesitate in picking the former WWE chairman, pointing to McMahon’s blunt style of feedback as the deciding factor.

“You know, I’m big on brutal honesty when it comes to bosses,” Riddle said. “For me, out of all of them, Vince was the best boss. If he didn’t like something you did, he didn’t wait. He didn’t say, ‘Good work.’ He told you right to your face that you messed up and needed to fix it, or you weren’t going to be there much longer. And you adapt, right?”　

Notably, Riddle’s reasoning centered entirely on what he valued about McMahon’s approach rather than any specific complaints about Triple H, Michaels or White. He framed it as a preference for directness over diplomacy — knowing exactly where he stood rather than receiving softened or delayed criticism.

The comments are worth noting given the current climate around McMahon, who stepped away from WWE amid ongoing legal issues and settlements tied to misconduct allegations that surfaced in 2022 and again in 2024. Since his departure, Triple H has run the company’s creative and talent relations operations, generally earning praise from the roster for being more collaborative and willing to involve wrestlers in storyline decisions — a contrast to the more autocratic reputation McMahon built over his four-decade run atop WWE.

Riddle himself had an up-and-down run in WWE, including a notable tag team pairing with Randy Orton as RK-Bro before his release from the company in 2023. He has since worked a mix of independent dates and other promotions, giving him a broader frame of reference for bosses across combat sports, including his time training and competing in MMA under Dana White’s UFC banner.

It’s a relatively small, almost offhand answer from a podcast appearance, but it’s the kind of comment that tends to generate discussion precisely because it cuts against the grain of how backstage dynamics are usually described these days. Most modern talent interviews tend to favor the Triple H era’s more open-door reputation, so hearing a recently departed talent credit McMahon’s old-school bluntness as more valuable stands out.

Whether that reflects something specific about Riddle’s own working relationship with each man, or simply a personal preference for directness over diplomacy, isn’t entirely clear from his comments. But it’s another data point in the ongoing, informal oral history of what it was actually like to work for Vince McMahon — as told by the wrestlers who did.