Hey Toughguy! Here is a little run through for each fighter.
Henry Armstrong
Wins: 150
Losses: 21
Draws: 10
Knockouts: 101
Notable opponents: Barney Ross, Lou Ambers, Ceferino Garcia.
Aaron Pryor
Wins: 39
Losses: 1
Draws: 0
Knockouts: 35
Notable opponents: Alexis Arguello, Sang Hyun Kim, Bobby Joe Young
Aaron Pryor in my opinion was the best of all time at 140 pounds, and Henry Armstrong never fought there, but Armstrong did fight at Featherweight, Lightweight, Welterweight, and Middleweight. Styles make fights, and this would be a classic, no doubt about it. They were about equal in size, and both men had pretty good chins. This would be a back and forth battle, with both men constantly throwing punches. Armstrong will have his moments, as will Pryor. At the end of the day, it will go to the judges and Henry Armstrong will get the razor thin split decision victory here.
The great thing about this question is that Armstrong and Pryor were considered mirror images of each other for a very long time. In many cases, such as with Larry Holmes and what will soon be the case with Wladimir Klitschko, some contemporary fighters gain momentum, in terms of respect, well after they retire. In plain English, they got they "just due" after retirement. In the case of Wladimir, he has yet to get his because he's still fighting.
Aaron Pryor went the other way, sorta. There are many die-hards who still swear that Ray Leonard ducked Aaron Pryor because Pryor was THAT BAD. I've always said that Roberto Duran, at 135-140 would beat both Pryor and Armstrong.
The difference with Pryor and Armstrong, now that both respective careers have settled into their respective places in history, is that Pryor never performed well at 147, while Armstrong ruled there. This tells me that Armstrong would have found a way to gut it out against Pryor.
Pryor would turn boxer by the middle rounds, once he realizes that "Hammerin Hank" isn't going anywhere. However, unlike Arguello, Armstrong isn't just there to be hit. He seemed to LIKE it. Pryor has power but it's not likely that he gets Armstrong out of there. It's more likely that Armstrong gobbles up that slight lead, that Pryor builds in the middle rounds, by roaring back to win on points.
Armstrong W15 UD
Man thats a tough one, compubox will break half way through the fight. both have similar styles so I'll go with the one who has more power and speed, Aaron Pryor
Armstrong did have better defense and maybe his in fighting will tire Pryor who fights at an extreme high pace. Still I'll give the slight edge to Pryor cause hes faster and punches harder
Pryor was great but he is overrated. WAY overrated. He had very few title defenses before getting whopped by some nobody. Prime Duran would have whopped him.
At 140lbs i think Armstrong would have beat him by decision. At 147lbs Armstrong would have killed him.
Armstrong is ranked the #2 best p4p fighter of all time by most experts.
Pryor isn't even top 30
If there was junior welterweight division in his days, Armstrong would have made it his home. In all his the forays from the featherweights through the welterweights and even the middleweights, Armstrong's average weight was just 138 lbs.,the highest he had weighed being at 144 when he fought and was held to a draw by Ceferino Garcia in his attempt to wrest his middleweight crown. This means that while essentially a junior welter, Armstrong was as strong as a super welterweight or even a middleweight in his prime best.
Pryor was considered as among the greatest junior welterweight champions in history in the company of Barney Ross, Tony Canzoneri, NIcolino Locche and the man he beat for his title Antonio Cervantes. But in his prime, he never forayed beyond 140 lbs. He fought at welterweight in his comeback after a drug-related semi-retirement and he suffered his lone career loss in the hands of fringe contender Bobby Joe Young who never lived up to the expectations as among the welterweights of the future alongside Marlon Starling, Donald Curry and Milton
Given those backgrounds, I think I am leaning on Armstrong with his prodigious strength competitive even at higher weights, over Pryor by UD or late round stoppage. Pryor never faded in the later rounds in his career but he had not fought in all his years against a buzzsaw with stronger freakish strength as Homicidal Hank!
Man, two of the all time greats. I'm going with Pryor, even with his drug problems. Still, it would probably be a 50/50 fight.
God only knows. I'd say Pryors superior boxing ability could have taken advantage of Hammering Hank's loose brawling style but it would be sacrilegious to pick against the Homicidal one.
at 140 lbs and 15 rounds