For Muhammad Ali, even a relatively mature version as he was after his return to boxing after having been stripped of his titles in 1967, it must have been disconcerting to tangle with an opponent like Oscar Bonavena, who challenged him in manyways even beyond the ring. The Argentinian was arguably as eccentric and voluble as Ali, often captivating fans and the media at weigh-ins and pre-fight press conferences that would rival Ali’s penchant for toying with the, ahem, delicate decorum of the sweet science.

In 1970, after taunting Ali with various racial remarks and chiding him about draft dodging, the wild-swinging Bonavena found himself having to answer for it when he faced Ali in Madison Square Garden in the former champion’s second fight after his three-plus years away from the ring due to legal entanglements. As he had done four years earlier in a similar 15-round confrontation with Joe Frazier, the exuberant Bonavena took an enormous amount of punishment against Ali, but not without administering some battering of his own.

In the 15th and final round, a crushing left hook from Ali decked the flailing Bonavena, who by now was charging ahead incautiously as the final bell neared. Controversy ensued when, as a disoriented Bonavena struggled to get to his feet, Ali hovered over him with these very same gloves only inches away, and promptly pummeled Bonavena twice more to the canvas. The three-knockdown rule gave Ali a TKO, the only time in Bonavena’s career that he was knocked out by an opponent.

His eccentricities would catch up with him in retirement as a romantic entanglement with the wife of the owner of the Mustang Ranch brothel in Reno, Nev., would end with a security guard killing Bonavena in 1976 with a rifle shot to the heart, putting a bizarre ending to the life of a significant figure in boxing lore and legend.

The burgundy Everlast gloves are in fine condition and are largely intact (no laces) and no difficulties with the iconic “Everlast” oversize tags on each wrist. The notation in white on underside of the fingers on each glove “21086 MSG” is clearly visible; there is minimal stitching loss on any of the light tan trim. Inside each glove is Angelo Dundee’s blue ballpoint notation “M. Ali and Bonavena” along with the date 12-7-70 on each wrist. A bold, black Dundee autograph appears in each glove below as does his period ballpoint pre-fight notation suggesting there would be a fourth-round KO.

Comes with Letter of Authenticity from Angelo Dundee on his personal letterhead.