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Four time Golden Gloves champion Dennis Milton passes away at age 64

James Slater

27th January, 2026

Four time Golden Gloves champion Dennis Milton passes away at age 64
Image credit: Top Rank

They called him “The Magician,” and on his best day, be that as an amateur boxer or as a professional, Dennis Milton of The Bronx, New York was indeed a very clever boxer who was capable of bewildering his ring rivals. Today, the sad news broke that Milton has passed away, this at the age of 64. Those people in the sport that knew Dennis are sending in their tributes.

Milton, who won no less than four Golden Gloves titles in the 1980s, with his amateur career also seeing him pick up a win over future three-weight world champion Iran Barkley, was, it’s fair to say, a fighter who flew largely under the radar. Or, perhaps a more accurate description of Milton’s less than well-documented career is that he toiled in the shadows.

Going pro in July of 1985, Milton compiled a 5-0 record, before he was beaten by another somewhat underrated fighter in Ismael Negron, who edged Milton via split decision over six sessions in Atlantic City in May of 1986. Both Milton and Negron would one day face the wrath of the fearsome-punching Julian Jackson.

Milton, would return to action just three months after the loss to Negron, and he would bag himself five more wins, before he was stopped in the fifth-round by Angel Sindo. Already, it had been tough for Milton to emulate his amateur success in the paid ranks. However, in the summer of 1989, Milton, now aged 27, strung together a run that, upon looking back, was pretty special.

In June, when fighting again in Atlantic City, Milton ran into a guy named Gerald McClellan. Six rounds later, future 160 lb terror McClellan was 10-1, and Milton had, in hindsight, picked up the biggest win of his career. In later interviews, Milton would refer to “G-Man” McClellan as “the most dangerous man I fought.”

Milton, enjoying a hot streak, went on to score a good win over Robbie Sims, the half-brother of middleweight great Marvelous Marvin Hagler, and “The Magician” then handed the skilled and tough Michael Olajide a close decision loss – “the toughest and the dirtiest guy I ever fought,” Milton would later say of Olajide. So, on his best night or nights, Milton was capable of beating a world class fighter, a future world ruler.

But unfortunately, Milton’s career had peaked with the trio of wins over McClellan, Sims and Olajide. Milton’s reward for this good spell was a shot at the feared Julian Jackson, the reigning WBC middleweight champ. In September of 1991, after scant seconds, Milton was to know first-hand just how power-packed a puncher “The Hawk” really was.

Losses to a future great, Bernard Hopkins, and yet another world champion, a former one in Aaron Davis, ended Milton’s career, with both defeats coming via stoppage.

Retiring with a more than decent 16-5-1 (4KO) record after the Davis loss, Milton became a trainer, one looking to give back to the sport he knew he would always love.

Dennis Milton was a fine boxer, and he met a number of big names and world champions during his amateur and pro campaigns. Our condolences go out to his family and friends at this time.

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