This duality remained a key theme throughout his early life until he witnessed racism as practiced in colonial Africa and later in the Jim Crow American South.

Massaquoi enjoyed a relatively happy childhood with his mother, Bertha Baetz, who had arrived in Hamburg from Nordhausen and earlier from Uftrungen.

His father, Al-Haj Massaquoi, was a prince of the Vai people who was in Dublin studying law and only occasionally lived with the family at the consul general's home in Hamburg.

[3] There was a school contest to see if a class could get a 100% membership of the Deutsches Jungvolk, a subdivision of Hitler Youth, and Massaquoi's teacher devised a chart on the blackboard showing who had joined and who had not.

After the Nuremberg Laws were passed in 1935, Massaquoi was officially classified as non-Aryan and barred from pursuing a course of education leading to a professional career.

A few months before he completed school, Massaquoi was required to go to a government-run job center, where his assigned vocational counselor was Herr von Vett, a member of the SS.

Upon seeing the "telltale black SS insignia of dual lightning bolts in the lapel of his civilian suit",[4] Massaquoi expected humiliation.

This by-fact of the Nuremberg laws, which were expanded in November 1935 to cover Afro-Germans, may however have saved him due from the devastating casualties, especially on the Eastern Front.

During the period following the Allies' near-destruction of Hamburg, he befriended the family of Ralph Giordano, a half-Jewish acquaintance of the surreptitious jazz devotees known as the Swing Kids.

The Giordanos, who managed to survive the war in hiding, helped Massaquoi and his mother to secure a nearby basement after their Hamburg neighborhood was destroyed.

He was interviewed in turn by Studs Terkel for his oral history The Good War, and related his unique experiences in Germany under the Nazi government.