Homicidal Hank vs Will o' the Wisp Would Henry be hitting air all night with one of if not the best pure boxer ever, or would Homicidal Henry dispatch of Pep ? 15 rounds.
Though seeing Willie Pep fight in his prime,and Henry Armstrong past his prime against Beau Jack and Ray Robinson, this does not influence my pick, I pick the featherweight killer of 1938, Armstrong to wear down Willie Pep by his ceaseless attack for a decision...Armstrong had to catch Pep sometime with his non stop attack...The FW Homicide Henry might have been the best featherweight ever in his prime...The ultimate elusive boxer versus the inhuman stamina of Armstrong. WOW !
I would pick Armstrong to win this comfortably over 15....I am not sure about a stoppage, but his work rate would ultimately see him win the day...Perhaps 10-5/9-6 or so.
Swarmers do well against defensive boxers, see Pep-Sadler, Mayweather-Castillo/Hatton, Ali-Frazier, Armstrong-Ross. So lean towards Armstrong
Armstrong has arguably just as quick reflexes as pep. Whilst pep would gloriously make his opponents miss by a mile at range before dancing away, Henry would have them miss by inches up close whilst landing relentless punches. The only way the slickster wins this fight is if he's big enough to keep the swarmed at range or hard hitting enough to cumulatively knock him out with clean blows. Pep is neither. I think pep wins the first 3 rounds whilst Henry finds his rhythm but ultimately Armstrong wears him down and stops him late.