This is total bullshit, and that is coming from someone who utterly loathes Rainbow Dash and would be ecstatic if she got even a fraction of Hitler’s hate from the fandom.
John F. Kennedy would be Princess Celestia (Adored Public figure who is also a sex fiend)
Queen Chrysalis would be Hitler, seeking to conquer the other races, who are sub-pony cattle to her, with her master race of changelings.
Abraham Lincoln is a stretch, but I’d say Mayor Mare. She’s in charge of a constantly disintegrating town, though Lincoln’s country was split idealogically while Ponyville is constantly getting destroyed.
Pinkie Pie is too stupid to be Leonardo. I’d say Reinessance mare Twilight is appropriate.
Fluttershy is a better John Lenon. Hippies and what not, though actually Ghandi isn’t too far off…
This is gonna make me unpopular, but Flim and Flam are the Steve Jobs of Equestria. They have an innovative, cutting edge piece of technology that is a breakthrough in it’s field, and despite questionable business practices, the product comes through.
And Osama would be Nightmare Moon. Blindly destroying over philosophical disagreements with no regards for consequence? Sounds about right.