One of the biggest upsets in Real American Freestyle (RAF) history just went down.
A massive +550 bet Michael Caliendo stunned American wrestling legend Jordan Burroughs earlier in the evening (Friday, October 23, 2026), defeating the Olympic gold medalist 8-5 at RAF 14 Fontainebleau Las Vegas in Las Vegas, Nevada.
And Caliendo didn’t steal the win with one lucky exchange — he battled Burroughs for most of the match.
The four-time NCAA All-American looked about three times the speed of the 38-year-old legend in the opening two periods, beating Burroughs into positions, running away from danger and frustrating him with constant movement.
By the start of the final frame, Caliendo had built an overwhelming 5-0 advantage and was minutes away from the unthinkable.
Burroughs finally found his vintage explosion in the third period and began another legendary comeback. The six-time world champion increased the pressure, forced Caliendo to back off and quickly erased most of the deficit.
But Caliendo refused to collapse.
Instead of panicking when Burroughs came back, the former Iowa Hawkeye stayed calm, fending off late attacks from the American icon and finding enough offense to secure a huge 8-5 loss.
Burroughs finished as a huge -800 betting favorite, while Caliendo finished at +550.
The result is easily the biggest win of Caliendo’s young career. The former Iowa standout finished as NCAA runner-up at 165 pounds in 2026, finishing his collegiate career as a four-time All-American and two-time national finalist.
Meanwhile, Burroughs entered RAF 14 with a bang after dominating the UFC lightweight contender. Sean Brady and Magomed Kurbanaliev in his first two appearances with a promotion. The 2012 Olympic champion had also publicly considered a second Olympic run in 2028.
At 38, Burroughs remains one of the greatest American wrestlers of all time, but on Friday night, youth and speed finally caught up with him.
Click for full results, coverage and highlights of RAF 14 HERE.
