This leap marks the first time Sam leaps into someone who directly affects history on a truly historical scale.
Sam's previous leaps all have him leaping in to affect individual lives that only have personal relevence within the leap.
Leaping into Oswald is the first of several leaps this season to have Sam interact with History through his relationship with historical figures. Others this season are:
"Lee Harvey Oswald"
"Goodbye, Norma Jean" and