Adolf Hitler: Tenured professor at Harvard.
Benito Mussolini: Political advisor to Obama
Josef Stalin: Tenured economist at Brown
Alexander the Great: Scientologist and Gay Civil Rights leader
William T. Sherman: Gentrification and land use consultant
Ulysses S. Grant: Former dry goods store owner testifying at AA meetings.
"Stonewall" Jackson: Baptist minister residing in Florida widely seen promoting orange juice consumption.
Napoleon: Tenured Professor at U Penn
Rommel: everything Shwartzkopf did, but even better. GOP would be trying to get him to run as the first German president of the US with Condaleeza Rice as VP. He would get Sherman to write letter of refusal.
George Washington: land surveyor, growing tobacco with Amish agricultural laborers.
Montgomery: (see "Alexander the Great" above)
Frederick the Great: writer for the National Review, Fox news military consultant.
Catherine the Great: SPCA volunteer.
Caesar: Would be doing everything Donald Trump does, but with class. His family would be in the tabloids constantly, however. Would have rights to the salad, of course, and a signed copy of Sinatra's greatest hits. Drives Ferrari with personal plate: "VVV", and his tax return states "olive oil importer".
Patton: Would be trying to get the nomination for president so he could be commander in chief and "make those poor dumb bastard terrorists die for THEIR beliefs".
Benedict Arnold: Senator for Massachussetts
Blucher: psychologist and self-help book writer.
Henry V: only successful English mafiosi