A lot of people wonder how Floyd Mayweather Jr. would he have done against the greatest welterweights of all time.

Perhaps no one on earth is in a better position to make that judgment than Don Chargin, a Hall of Fame matchmaker and promoter who has seen them all since breaking into the boxing business in 1945.

With that in mind, RingTV.com asked Chargin to name the five best welterweights he saw fight and indicate how Mayweather would’ve fared against them.

The five fighters: Ray Robinson, Sugar Ray Leonard, Tommy Hearns, Roberto Duran and Wilfredo Benitez.

Chargin, a consultant for Golden Boy Promotions, thinks a lot of Mayweather. He believes “Money” would’ve given any welterweight in history – except one (see below) – trouble in the ring.

“Do I respect Floyd? Oh yeah,” Chargin said, “The main thing is his work ethic. I’ve seen him in the gym. I don’t think I’ve ever seen a fighter who works harder than him. And Floyd is very, very talented.

“He could’ve boxed with any of the five guys we’re talking about. Only one would’ve been a big favorite over him.”

RAY ROBINSON vs. MAYWEATHER

Chargin said he saw Robinson fight “seven, eight times,” mostly as a middleweight. However, he was there when Robinson fought Earl Turner in a welterweight bout in 1949 in Oakland, Calif. Robinson was 28 and at or near his peak at the time.

Robinson is widely considered to be the greatest fighter of all time.

“Robinson would’ve handled Floyd easily,” Chargin said. “He was so tall [5-foot-11] and everything. He had all the physical attributes. Great jab. He punched with the right hand. He punched with the hook. He had a great chin. His only weakness was old age after he fought too long.

“And as quick as Floyd is, I don’t think he could match Robinson in quickness. I think Ray would’ve boxed Floyd silly. He could even have stopped Floyd in the late rounds. I’m not being critical of Mayweather at all. Robinson was just that good. He was head and shoulders above everyone.”

Prediction: Robinson by late KO.

SUGAR RAY LEONARD vs. MAYWEATHER

“I think Leonard would have won. I was just talking to Teddy (Atlas) about this. I think Leonard would’ve gone after Floyd. Ray would’ve boxed but he also had the ability to finish. ÔǪ Strictly boxing? They would be very, very close. Leonard was a better puncher, though. Once Leonard hurt you, he went in to finish that job. I always admired that.

“I think Floyd would’ve given Ray trouble.  He would’ve given any of the five trouble except Robinson. I just think Leonard was a little better.”

Prediction: Leonard by decision

TOMMY HEARNS vs. MAYWEATHER

“This might be the toughest one to predict. With one punch, Hearns could change everything. He was that kind of puncher. He was a real fighter. And he looked like he always enjoyed it. I really liked watching him fight. His fights were always exciting, even the fights he lost. He gave you everything you want.

“If Floyd decided to sit down on his punches, he would have more power (than he typically demonstrates), but he doesn’t want to. Hey, you can’t knock success. He fights the way he fights.

“Hearns also had that height (6-foot-2) and reach. And when you think of Hearns, you think of just a puncher, but he could really box. I think Mayweather would have a good chance but I really believe Hearns would win.”

Prediction: Hearns by decision

ROBERTO DURAN vs. MAYWEATHER

Duran was a lightweight when he fought twice for Chargin in Los Angeles in 1973, against Juan Medina and Javier Ayala. He began to fight as a welterweight in the late 1970s.

Chargin pointed to Duran’s second fight against Leonard, when Leonard outboxed the Panamanian in the famous “no mas” fight, as an indication of what Mayweather might’ve been able to accomplish.

“Duran was probably one of the top lightweights of all time. And he was still a great fighter at welterweight,” Chargin said. “His toughness, mental toughness, punching power, great chin. He had everything.

“I think a fight with Mayweather would’ve been very, very close. And Mayweather could win. One thing he’d have over Duran is speed. I think he would’ve been too fast, too good a boxer for Duran. I’m picking Floyd.”

Prediction: Mayweather by decision

WILFREDO BENITEZ vs. MAYWEATHER

Chargin was the co-promoter when Carlos Palomino traveled to Puerto Rico in 1979 to fight Benitez, who took Palomino’s welterweight title by a split decision.

“Benitez was a great boxer. He had good hand speed, a good jab. Him and Flody would’ve been a clinic on boxing, how to throw proper punches and everything. I think Floyd would be a little too much for him. Benitez was hurt many times in his career. I think Floyd would caught him, built a big lead.”

Prediction: Mayweather by decision

Photo by Naoki Fukuda