Flair’s first WWE stint began in 1991, following his legendary run in the NWA and WCW. Though primarily known as a WCW icon, Flair acknowledged that working with Vince McMahon introduced him to the larger-scale WWE operation and its unique style of sports entertainment. According to Flair, the business dealings in the early 90s were tough but fair, with Vince operating as a shrewd promoter focused on building stars and the company brand[1][3]. Flair has mentioned in interviews and podcasts that, while he never fully felt like a “WWE guy” back then due to his predominant association with WCW, he respected McMahon’s vision and business acumen.
A WWE insider told Fightful recently that Vince McMahon and Ric Flair’s initial relationship was marked by a blend of mutual respect and professional boundaries, with Vince recognizing Flair’s legendary status and Flair acknowledging the importance of the WWE platform. The insider noted that Vince lent Flair financial support during difficult personal times in later years, further cementing their complicated friendship beyond just the business side[1]. This element was highlighted in a 2023 statement from Flair, who publicly defended Vince amid controversies, calling him his “hero” and emphasizing the loyalty developed through years of professional and personal trials.
The peak of their early 90s WWE storyline collaboration came in the early 2000s with the Invasion angle and Ric Flair’s role as a WWF co-owner during a turbulent time following the acquisition of WCW and ECW. Flair and McMahon engaged in a heated on-screen rivalry, battling for control of the company—a storyline culminating in a street fight at the 2002 Royal Rumble, which Flair won[3][4]. Off-screen, their rapport remained professional as the wrestling business underwent significant corporate changes.
Multiple sources, including WWE.com and interviews on various wrestling podcasts, emphasize the business-minded approach Vince applied to his dealings with Flair and other wrestling legends. Jim Cornette, in a YouTube interview, pointed out that Vince McMahon was always more focused on talent who fit WWE’s brand direction, but he still respected Flair’s wrestling credentials even when their working relationship was at times challenging[5]. Flair himself has described those early 90s dealings as tough but necessary business.
Their relationship evolved dramatically in later years, with Flair returning to WWE multiple times in various capacities including on-screen talent, backstage mentor, and storyline authority figure. Sources close to Cody Rhodes revealed that Flair’s influence and experience with Vince shaped many backstage philosophies in WWE, and Flair’s legacy is still acknowledged by McMahon’s inner circle today[1].
Overall, Ric Flair’s remembrance of his business dealings with Vince McMahon during the early 1990s paints a portrait of two iconic figures navigating the wrestling industry’s shifting landscape. Their professional and personal relationship, though complicated, was significant to the growth of WWE in that era. The mutual respect they cultivated helped lay the foundation for historic wrestling moments and behind-the-scenes collaborations that still resonate in WWE culture[1][3][4].