Only two people have received the Presidential Medal of Freedom twice.
Alongside the Congressional Gold Medal, the Presidential Medal of Freedom is the highest civilian award in America. An average of roughly 10 awards per year have been bestowed since the honor was first created by John F. Kennedy in 1963 (though some presidents award more medals than others), and only two people have received more than one: Ellsworth Bunker and Colin Powell. The former, a career diplomat who served six different U.S. presidents as the ambassador to Argentina, Italy, India, and South Vietnam, received his in 1963 and 1967, both of them with distinction — an additional level of veneration reserved for approximately 8% of recipients.
Powell, meanwhile, earned his awards in 1991 and 1993, the second with distinction. He received the first from George H.W. Bush and the second from Bill Clinton, both of whom he served under as chairman of the Joint Chiefs of Staff; he had previously been Ronald Reagan’s national security adviser and later became secretary of state for George W. Bush. While presenting Powell with his first medal at the end of the Gulf War, the elder President Bush said, “Your commitment and good counsel, your deep compassion for every one of the thousands of men and women under your command, will always be remembered.”