Prinz Oskar was born on July 27, 1888, a month after his father had become the German Emperor.
Education
Prinz Oskar was educated as a cadet at Plön, in his mother’s ancestral Schleswig-Holstein, as his brothers had been before him. He made the news in 1902 when he fractured his collar bone after a fall from the horizontal bars.
Military career
During the early months of the First World War, he commanded Grenadierregiment "König Wilhelm I." Nr. 7 in the field as its colonel. Future fighter ace Manfred von Richthofen witnessed the 22 August 1914, attack on Virton, Belgium, and wrote of Prinz Oskar’s bravery and his inspirational leadership at the front of his regiment as they went into combat. For this action, Oskar earned the Iron Cross, Second Class. A month later, at Verdun, Oskar again led his men in a successful assault into heavy combat, and was awarded the Iron Cross, First Class. After this action, he also collapsed and had to be removed from the field. Awarded the wound badge for his injuries, he spent much of the fall of 1914 recovering from what was reported to be a heart condition. He eventually returned to duty and served on the Eastern Front, where he was again awarded the wound badge. In the early 1920s, his name was listed with other members of the general staff or the royal family accused of war crimes, and was condemned in the Press for applying for a colonel’s pension from the Weimar Republic. During the 1930s, when the Hohenzollern family attempted to test the waters for a return to power through Nationalist Socialism, Oskar appears to have played along, and eventually was commissioned at Generalmajor zur Verfügung, circa March 1, 1940. As the family fell out of favor with Hitler, it became evident that there would be no restoration of the monarchy through the Nazis. With the early battlefield deaths of Oskar’s son and his nephew the German people harbored a newfound sentiment for the royal family amidst the totalitarian regime that was Nazi Germany. As a consequence, the majority of royals serving in the German Armed Forces appear to have had their commissions canceled, including Prinz Oskar.
The Johanniterorden was a favorite of the Hohenzollerns, historically, and of Prince Oskar’s immediate family specifically. His father and uncle were members, and his brother, Eitel Friedrich, served as its Master of Knights, from 1907 to 1926. Prinz Oskar served as the thirty-fifth Master of Knights from Eitel Friedrich's resignation in 1926 until his death in 1958. Modern historians credit Prinz Oskar for saving the ancient order from oblivion during the cultural purges of the Nazi regime. It is from this struggle that he held his anti-Nazi sentiments. After his death in 1958, his youngest son, Prinz Wilhelm Karl, became his permanent successor. Prinz Oskar's grandson and namesake, Dr. Oskar Hohenzollern, is the current Master of Knights.
Prince Oskar, whose health declined during the final years of his life, died of stomach cancer in a clinic in Munich on 27 January 1958, on what would have been his father's 99th birthday.