Lots of skill sin this match up. To give Pep an advantage, lets say Leonard has to make weight of 130 pounds 48 hours prior to the fight.
Yes Benny Leonard vs Willie Pep. Could Pep's speed and great defense neutralize Leonard's wonderful stand up boxing skills? I'll side with Leonard.
So will I. It was he who suggested to Tunney that Gene focus on Greb's body after their first meeting, and it was a body attack which enabled Saddler to upset Willie in their first encounter. Benny wouldn't take out a peaking Pep, but he'd score enough to win on points. Willie had tremendous natural gifts, but Leonard had the head to overcome them.