It’s hard to pick who of all Muhammad Ali’s opponents was the toughest. There were the early fights against Liston and Patterson that made his name. Then there were the marquee grudge matches of Joe Frazier and their “Fight of the Century” and “Thrilla in Manilla,” and the “Rumble in the Jungle” against George Foreman. Of course, there were the three Chuck Wepner fights that inspired Sylvester Stallone to write Rocky. If there was a tough heavyweight from 1960 to 1980, Ali fought him. But when the question of “who was the toughest” was put to Ali himself, The Champ unequivocally replied, “George Chuvalo.”

Ali fought George Chuvalo two times, and each time the Canadian heavyweight went the distance. The first was in 1966, with Ali successfully defending his title after 15 bloody rounds. Ali told reporters after the fight, "He's the toughest guy I ever fought.” Six years later the two met again, this time in a NABF Heavyweight Title Fight in Vancouver’s Pacific Coliseum. Again, their fight went all 15 rounds. Ali had predicted beforehand that he would drop Chuvalo, who had never been knocked down in the ring before. Despite Ali’s most devastating punches, the Canadian refused to go down. Again and again, Ali unleashed devastating combinations that would have floored any other fighter, but Chuvalo stayed grounded. At one point in round 5, Ali stood still in the corner, daring Chuvalo to hit him. Finally, at the end of 15, both men were still standing, each never having been knocked down. Like their first meeting in 1966, Ali won the decision by a wide margin, but came away with even more respect for the toughness of his opponent that night.

These are the trunks Ali wore facing George Chuvalo in their epic second meeting. The trunks were gifted to referee Davey Brown who in turn passed them to his daughter. The trunks are white with black waistband and stripes and the Everlast label is sewn to the front outside waistband. Despite going 15-rounds hard-fought with Chuvalo, Ali’s trunks are in excellent condition except for faint yellow staining on the lower right front side. To add to Davie Brown’s provenance, the trunks have been authenticated and photomatched by RGU Photomatching comparing photo stills of the fight against distinct areas found on the Everlast label and stitching on the waistband.

Adding to the already historic importance of these trunks are the addition of both Muhammad Ali’s and trainer Angelo Dundee signatures. Both boxing icons have signed the rear seat of the trunks, Ali in blue marker with a personalization to Davey Brown and Dundee in black marker. Any Muhammad Ali fight-worn pieces are noteworthy, but to come across the photomatched trunks The Champ wore while facing who he called “the toughest guy I ever fought,” is extraordinary. This artifact of boxing history comes with a plethora of documentation including a letter of provenance from the Brown family, LOA from JSA for the signatures, LOA from world renowned boxing authenticator Craig Hamilton of JO Sports, LOA from RGU photomatching service and LOA from Sports Investors Authentication for an additional photomatch.

ESTIMATE: $50,000+