Ric Flair has plenty of respect for Kenny Omega and Will Ospreay, but he is not ready to place their acclaimed rivalry alongside his legendary series with Ricky Steamboat.
The debate began after a fan described Omega and Ospreay’s AEW All In main event as the greatest match in professional wrestling history. Music star and longtime wrestling fan Darius Rucker rejected that assessment with a straightforward response.
“You obviously never saw Flair vs. Steamboat,” Rucker wrote.
Rucker subsequently called Flair the greatest wrestler of all time. Although he praised the work being produced by WWE, AEW and other modern promotions, he argued that today’s wrestling cannot recreate what made the territory era feel special.
Thank You @dariusrucker For Always Having My Back! Because There Is Something Wrong Where People These Days Can’t Seem To Use Their Real Name Online. Just Learn How To Use Your Real Name Before Expressing Your Opinion. It Would Be Very Helpful For All Of Us. pic.twitter.com/glXDOzL6DT
— Ric Flair® (@RicFlairNatrBoy) September 1, 2026
Flair later entered the discussion himself. The WWE Hall of Famer praised Omega and Ospreay as outstanding talents but said comparing their rivalry to his matches with Steamboat was like comparing the Mississippi River to the Pacific Ocean.
“No One Has More Respect For @KennyOmegamanX And @WillOspreay Than Me! But To Compare Them To Steamboat And I Is Like Comparing The Mississippi River To The Pacific Ocean! When They Have A Great Match 300 Times A Year And 200 Hour Broadways, Get Back To Me! Until Then, There Is No Problem With Being Number Two. You Are Great Young Talent, But Let’s Get Serious Kids! You Should Only Hope That You Have People Talking About Your Matches 37 Years Later! WOOOOO!,” Flair wrote.
The Nature Boy’s argument focused largely on repetition and longevity. Flair invoked the demanding schedules of his era and the numerous lengthy matches he worked with Steamboat, including multiple contests that reached a 60-minute time-limit draw. Flair said Omega and Ospreay should hope people are still discussing their matches 37 years from now. Until they have built that kind of enduring legacy, he believes they should be comfortable occupying second place.
No One Has More Respect For @KennyOmegamanX And @WillOspreay Than Me! But To Compare Them To Steamboat And I Is Like Comparing The Mississippi River To The Pacific Ocean! When They Have A Great Match 300 Times A Year And 200 Hour Broadways, Get Back To Me! Until Then, There Is No… pic.twitter.com/UFqcgPg8Zs
— Ric Flair® (@RicFlairNatrBoy) September 2, 2026
The Flair-Steamboat rivalry is most closely associated with its celebrated 1989 trilogy for the NWA World Heavyweight Championship. Steamboat defeated Flair at Chi-Town Rumble, retained the championship in a nearly hour-long two-out-of-three-falls match at Clash of the Champions VI and lost the title back to Flair at WrestleWar.
Those three televised encounters represent only part of their history. Flair and Steamboat wrestled each other extensively at live events throughout the late 1970s and 1980s before returning to the rivalry again in 1994.
Omega and Ospreay added another major chapter to their own series Sunday at Wembley Stadium. Ospreay defeated Omega in the All In main event to capture the AEW World Championship for the first time. That victory gave Ospreay a 2–1 advantage in their modern trilogy, which began with Omega winning at Wrestle Kingdom 17 in January 2023. Ospreay answered at Forbidden Door that June before prevailing again at All In. However, Omega also defeated Ospreay during a PWG event in December 2015. Including that earlier encounter, their complete singles record is tied at two victories apiece.
Comparing the two rivalries ultimately requires judging matches produced in dramatically different eras. Omega and Ospreay have delivered three prominent modern showcases, while Flair and Steamboat built their reputation through years of repeated performances. For Flair, that difference in volume—and the fact that the 1989 trilogy remains influential nearly four decades later—ends the debate before it begins.
