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The first meeting with Vince McMahon is intimidating for most, if not every WWE Superstar. He is ultimately the man that everybody answers to, and there are several stories of large men getting intimidated to enter his office or even knock on his door.
Vince McMahon's presence can often be intimidating, and many superstars have fumbled or had an awkward first meeting with the Chairman of WWE. Here are five legends and World Championship-level superstars who had an awkward first meeting with the boss:
#5. Drew McIntyre - Thought he messed up his WWE career when he first met Vince McMahon
Drew McIntyre is a superstar who Vince McMahon has a lot of respect for. He made a prophecy in 2009 by introducing McIntyre as a "future world champion" not long after his debut.
Dubbed as "The Chosen One," he seemed destined for World Championship glory in WWE - especially with direct backing from McMahon. Various issues outside the ring and perhaps a change of mind from Vince McMahon led to Drew McIntyre drastically falling down the card.
His run with 3MB, while entertaining, wasn't suited to him at all and proved to be a death sentence in his first WWE run. In 2014, five years after McMahon's declaration, McIntyre was released from WWE.
Speaking to Ryan Satin on his Out of Character show, Drew McIntyre admitted that he had an awkward first meeting with Vince McMahon:
"The first [meeting with Vince] was on my first day on the road. I sat in catering and I remember he sat in front of me and I panicked." Drew McIntyre said, "I introduced myself, he knew who I was. He gave me some advice and I mumbled some stuff in my very thick Scottish accent, especially back then. He stood up, nodded, walked off and I thought 'I just messed up my whole WWE career'. Vince McMahon did not understand a word I said," said Drew McIntyre.
McIntyre's release from WWE proved to be a big chip on his shoulder, as he would spend the next three years traveling the world and refining his skills and improving his physique. He had a successful stint with IMPACT Wrestling and ended up jumping ship to WWE in 2017. While he joined NXT and won the NXT Championship within months, his run would be cut short by a bicep tear when he lost the title to Andrade.
When he returned, it was straight to Monday Night RAW. The new and improved Drew McIntyre impressed Vince McMahon, who seemed determined to fulfill the prophecy he had made several years earlier. It culminated in 2020 with a Royal Rumble victory for The Scottish Warrior and a WWE Championship at WrestleMania 36.
Despite his awkward first meeting with the WWE Chairman, McIntyre has come far. The fact that he carried the company on his shoulder during the COVID-19 era proves how much trust Vince McMahon has in him.
Despite Drew McIntyre taking a back seat in 2021, it's unlikely that his run at the top is over.
#4. John Cena - Vince McMahon was "disgusted" when he first saw him
While most WWE Superstars are nervous to meet Vince McMahon for the first time, John Cena claimed that he simply "didn't have the time" to feel that way. It was June 27th, 2002 - three days after McMahon made a declaration to the young WWE roster that he wanted to see "Ruthless Aggression" from them.
Cena made his debut on SmackDown against Kurt Angle in what has become an iconic moment. When Angle asked the 25-year old what he possessed to think that he could stand in the same ring with an Olympic Gold Medalist, Cena simply said "Ruthless Aggression" before launching an assault.
Interestingly enough, John Cena revealed that he wasn't even supposed to wrestle that day. It was a last-minute decision that made some officials realize that they needed Cena to meet McMahon.
Talking to WWE.com, John Cena revealed that Vince McMahon saw him when he was blond and the Chairman looked "disgusted":
“They literally dragged me by the arm to Vince’s office, threw me in and asked him, ‘What do you think?’ I had ridiculously ugly, long, super-dyed blond hair that was shaved bald on the sides. He turned around and with a disgusted look on his face, he said, ‘Cut his hair,’ and I was whisked away from Vince like an assembly line," said John Cena.
Cena said that the disgusted Chairman Vince McMahon ordered him to get a haircut:
“That was the first time I met Vince McMahon and he was disgusted to look at me. They shipped me out and I immediately got a haircut, which was not dyed blond, but equally as horrible."
It isn't the best first impression to have, but three years later, McMahon was convinced that Cena was going to be WWE's franchise player. Vince McMahon later declared John Cena as the "Babe Ruth of WWE".
#3. Daniel Bryan - An "awkward and uncomfortable" first meeting with Vince McMahon
Daniel Bryan took a few years to truly win Vince McMahon over, but his talent was quickly recognized. Interestingly enough, he was signed to a developmental contract with WWE in 2000-2001 and made a few appearances in the company without a contract between 2002 and 2003.
However, Bryan's first interaction with McMahon took place in 2008 when he was with Ring Of Honor. A blocked number appeared on Daniel Bryan's phone, but he picked it up anyway, with the person on the other line saying "Hi, this is Vince McMahon".
While Bryan thought he was joking at first, he went with it, and the WWE Chairman told him that Shawn Michaels spoke very highly of him. He called for a meeting and ended up in Oakland where RAW was being taped.
Bryan detailed his meeting with Vince McMahon to WWE.com, saying:
“I didn’t even know how to sit in a suit. He asked me things like, ‘What would you like to see happen?’ I told him that I’d like to come in and be a top guy, but I had concerns about not being very big. I have a very self-deprecating sense of humor and think of myself as a humble person, so it’s hard for me to say that I’m good at something. Vince said, ‘Shawn tells me you’re very good.’ And I just said, ‘Well, I’m okay.’ And I could tell instantly he disliked that."
Daniel Bryan summed up his first meeting with Vince McMahon as "awkward and uncomfortable.":
“It was very awkward and very uncomfortable. Vince takes these very long pauses after he asks you a question and you answer him. He’ll just look at you. Some will start talking, which I think he likes because it shows they’re uncomfortable. I was uncomfortable, but I just looked at him. I was waiting for him to talk and he was waiting for me to talk. It was surreal," added Daniel Bryan.
Thankfully, their relationship grew and McMahon recognized Bryan's potential. Five World Championships, a decade-long tenure, and two WrestleMania main events later, it's safe to say that Vince McMahon sees Daniel Bryan for the talent that he is.
#2. Riddle - Vince McMahon didn't want him to be "goofy"
Riddle once appeared on WWE's The Bump and detailed his awkward first encounter with Vince McMahon. The King Of Bros told McMahon that he fought in the UFC and was "kind of goofy". The Chairman of WWE didn't have the desired response:
"At first, everybody was really hesitant, even Vince. Everybody was like “Oh…” I remember when I was in his office, so I was like “Yeah I fought in the UFC, I’m kind of goofy.” He said, “Goofy? That’s not good!” I was like “What? Being goofy is awesome! I’m fun, I’m feeling good, I’m goofy!” He was like, "(Imitates Vince McMahon’s voice) You don’t want to be a goof.” I was like, “I do wanna be a goof! Maybe you don’t want a goof here, but I wanna be goofy. But I’m also a killer too! I fought in the UFC, I won world championships and everything!” So it’s like, you’ve got to realize, I’m a very Ying Yang character. I’ve got dimensions, different levels," said Riddle.
It's yet to be seen how Riddle will do in the long run. He's been on the WWE main roster since the summer of 2020 and has a United States Championship to his name. He has also formed an unlikely alliance with Randy Orton.
He undoubtedly has to prove himself to McMahon more than anyone else. Since Riddle mentioned the skepticism that Vince McMahon had at first about his character, there's a long way to go before he takes the next step.
#1. The Undertaker - Vince McMahon had "nothing" for him in their first meeting
The Undertaker is the greatest character that Vince McMahon ever created and there's no disputing it. In an era where superstars got gimmicks selected randomly from a box, The Phenom stood the test of time to become an immortal in the wrestling industry.
In his prime, there was no wrestler in the world more respected than The Undertaker. A legend and locker room leader, he had a presence and authority about him.
But years before he was the most respected man in wrestling, The Deadman was in an extremely tricky position. He wrestled in WCW before, but the higher-ups told him that people would never pay to see him. Stating that it only made the chip on his shoulder grow, he sought out to sign with WWF/E through his connections with Paul Heyman (his manager) and Bruce Prichard.
While Vince McMahon wasn't impressed with "Mean" Mark Callaway at first, he relented to Prichard's requests and met The Undertaker. The Phenom told Peter Rosenberg on his Cheap Heat podcast that his first meeting with the WWE Chairman ended awkwardly as there was nothing for him:
"I’m working in WCW without a contract. We finally went to the Meadowlands [Arena] I think, the next morning i had a meeting at [Vince’s] house. Even then, I went in thinking, I got this. I had the meeting, maybe two hours i spent with Bruce and Vince and JJ Dillon and Pat Patterson. I have this meeting and think i’m being impressive and charming. At the end of the meeting Vince looks at me and goes, ‘We don’t really have anything right now.’ (laughs). I already gave my notice thinking, I’ve got the meeting, the job’s in the bag, Ive already given my notice down at WCW,” said The Undertaker. (H/T SEScoops)
The Undertaker went on to reveal that Vince McMahon told him there would possibly be an opening after WrestleMania. After his involvement with Hulk Hogan in Suburban Commando (a movie that The Undertaker described as the "worst ever"), he got the call and eventually debuted at Survivor Series 1990.
Vince McMahon was looking for the right man to fit The Undertaker character, and Mark Callaway was it. The rest, as they say, is history.
