In his autobiography, Destined to Witness, Massaquoi describes his childhood and youth in Hamburg during the Nazi rise to power. His biography provides a unique point of view: he was one of very few German-born mulattoes in all of Nazi Germany, shunned, but not persecuted by the Nazis. This dichotomy remained a key theme throughout his whole life.

Massaquoi lived a simple, but happy childhood with his mother, Bertha Nikodijevic. His father, Al-Haj Massaquoi, was a law student in Dublin who only occasionally lived with the family at the consul general home in Hamburg. Eventually, the consul general was recalled to Liberia, and Hans Massaquoi and his mother remained in Germany.

The daily life of the young Massaquoi was remarkable. He was one of the few mixed race children in Nazi Germany, and like most of the other children his age, he thought about joining the Hitler Youth. There was a school contest to see if a class could get a 100% membership of the jungvolk and Massaquoi's teacher devised a chart on the black board which showed who had joined and who had not, and as this was filled in after each person joined it made Massaquoi feel left out and he recalled saying, "But I am German...my Mother says I'm German just like anybody else".He then convinced his mother to let him join the jungvolk. He went to register at the nearest office but he faced hostility.

As a non-Aryan, Massaquoi was unable to pursue a professional career and instead was encouraged by his mother to embark on an apprenticeship with a view to becoming an expert machinist. A few months before finishing school, Massaquoi was required to attend a government-run job centre where his assigned vocational counsellor was Herr von Vett, a member of the SS. Upon seeing the 'telltale black SS insignia of dual lightening bolts in the lapel of his civilian suit', Massaquoi expected humiliation. Instead he was surprised when he was greeted with 'a friendly wink', offered a seat and asked to present something which he had made. After presenting von Vett with an axe and discussing his experience in running a local blacksmith shop, Massaquoi was surprised to be informed that he could 'be of great service to Germany one day' because there would be a great demand for technically trained Germans, who would go to Africa, and train and develop an African workforce when Germany reclaimed its African colonies. Before Massaquoi left the interview, von Vett invited him to shake his hand which was another source of confusion to Massaquoi.

Massaquoi dated a German girl and they had to keep their relationship a secret especially as her father was a member of the police and the SS. To keep their relationship secret they could only meet up in the evenings, where they would go for walks. As he dropped his girlfriend off at her house one night, after one of their walks, he was stopped by a member of the SD, the intelligence branch of the SS. He was taken to the police station as he was believed to be "on the prowl for defenceless women or looking for an opportunity to steal".

Fortunately for Massaquoi, he was recognised by a police officer as a living in the area and working; "this young man is an apprentice at Lindner A.G., where he works much too hard to have enough energy left to prowl the streets at night looking for trouble. I happen to know that because the son of one of my colleagues apprentices with him".The SD officer closed the case, gave the Hitler salute and Massaquoi was allowed to leave the station.

Increasingly, however, he realized the true nature of Nazism. His skin color made him a target for racist abuse. However, in contrast to German Jews or German Roma, Massaquoi...as a German Negro...was not persecuted. He was "just" a second-class citizen, which was actually a blessing in disguise. During World War II, his "impurity" spared him from being drafted into the German army. As unemployment, hunger and poverty grew rampant, he even tried to enlist, but he was rejected by the officers.In this time, he befriended the family of Ralph Giordano, a half-Jewish acquaintance of their swing kid age, who survived the war by hiding and ended up being a journalist as well.

In 1947 Massaquoi was able to visit Liberia, and was fascinated and shocked by its raw, rural nature. He grew estranged from his father Al-Haj, who left his mother and who came across as arrogant and tyrannical.

Massaquoi then emigrated to the United States. He served two years in the army as a paratrooper in the 82nd Airborne Division. With his GI bill he studied journalism at the University of Illinois followed by a career at Jet magazine and then Ebony magazine, where he became managing editor.His position allowed him to interview many historical figures of the arts, politics and civil rights movement.

Over the years he has visited Germany many times. He states Germany is still his homeland.