On June 13, 2015, Cain Velasquez entered the Octagon at UFC 188 as a prohibitive favorite, around -450 on most sports books and as high as 7-to-1 in places. Certainly, Velasquez was riding high; after his first career loss to Junior dos Santos, he had ripped off four straight wins in completely dominant fashion, smashing dos Santos and Antonio Silva twice each to cement his hold on the Ultimate Fighting Championship title. However, Werdum was riding a five-fight win streak of his own since rejoining the UFC, culminating in him halting the feel-good story of Mark Hunt and picking up the interim belt the previous November.
The lopsided odds probably were owing in part to Velasquez’s near-bulletproof résumé; while he was prone to injuries in training, in the cage his only loss had been a stunning first-round knockout at the hands of dos Santos, which required a kind of power that Werdum appeared to lack. Meanwhile, “Vai Cavalo” was an undeniably gifted and dangerous fighter—perhaps the greatest heavyweight grappler in MMA history—who was prone to showing up in questionable shape, as had happened in his own first-round loss to dos Santos, or putting in strangely flat performances, as he had done in two fights against Alistair Overeem.
That night in Mexico City, however, upended the expectations of every sports book and the vast majority of fans. Werdum had prepared for the 7,000-foot altitude of the host city, conducting most of his camp at high altitude, and when the two men appeared in the Octagon, “Vai Cavalo” was in the best shape of his career. After losing the first round to the trademark pressure and pace of Velasquez, Werdum won the second as that pace slowed, busting up Velasquez’s left eye with punches and rocking him with several huge knees. By the third round, the man popularly known as “Cardio Cain,” one of the best-conditioned heavyweights ever, was clearly the more tired fighter. After absorbing a couple more knees, Velasquez shot for a takedown, only to be ensnared in a guillotine choke. Seconds later he tapped out, and one of the biggest upsets in UFC title bout history was complete.
From there, Werdum would lose the belt to Stipe Miocic in his next outing, but remained a top-level contender until 2018, when he was slapped with a two-year suspension by USADA for performance-enhancing drugs. In his return bout last month, he lost narrowly to Top 10 contender and fellow 40-something Alexey Oleynik. Velasquez has fought only twice since that night, blowing away Travis Browne and being leveled by Francis Ngannou, in between lengthy injury layoffs and a stint as a professional wrestler.