Dressed in a white shirt and tie, Jacob went to the Oval Office with his family for a photograph to mark the end of his father’s posting on the National Security Council.
As the family posed for pictures, his father, Carlton, told Barack Obamathat Jacob wanted to ask the Commander-in-Chief a question.
In a voice so quiet Mr Obama could barely hear him, Jacob said: “I want to know if my hair is just like yours,” according to the New York Times.
Leaning down so his head was level with the boy, Mr Obama answered: “Why don’t you touch it and see for yourself?” Jacob hesitated but was encouraged after the President told him “Touch it, dude!” With eyes wide, Jacob reached up with his right hand and patted Mr Obama’s short, and slowly greying, hair. “Yes, it does feel the same,” he said.
The moment, captured by the White House’s official photographer, has come to symbolise the importance of Mr Obama’s presidency to African-Americans.
“It’s important for black children to see a black man as president. You can believe that any position is possible to achieve if you see a black person in it,” said Mr Philadelphia, who is now posted to Afghanistan with the US State Department.
The photograph, taken in 2009, has hung in the West Wing for three years unlike many Oval Office pictures which are reshuffled each week.
Jacob, now eight, told his father that he either wants to be president or a test pilot.