07.1918: volunteered in the Heer
1922: graduated from Infanterieschule München of the Reichswehr
01.04.1922: RDA Leutnant (4a)
01.04.1924: Ausbildungsbatterie - Artillerieregiment 3 - Potsdam
01.02.1927: promoted to Oberleutnant (20) and served in support of the General Staff
01.04.1934: promoted to Hauptmann (18)
01.02.1935: Kriegsakademie - Berlin
15.10.1935: Ib - Generalstab der 21. Division - Elbing
12.10.1937: Chef der 4. / Artillerieregiment 33 - Landau
01.08.1938: promoted to Major i.G. (1) with RDA 01.08.1937 (19a) and joined the General Staff in the Organisationsabteilung (coordination department) as Leiter der Gruppe III under Major Adolf Heusinger
01.11.1940: promoted to Oberstleutnant i.G. (18)
September 1941: Ia - Stab / IV.Armee
01.06.1942: promoted to Oberst i.G. (12)
Recognized for his excellent organizational skills, Stieff in October 1942 was appointed Chief of Organisation at OKH - Chef der Organisationsabteilung im Generalstab des Heeres - despite Hitler's strong personal dislike. Hitler called the young, diminutive Stieff a "poisonous little dwarf."
From the 1939 Invasion of Poland onwards, Stieff conceived an abhorrence for the Nazi military strategy. When in Warsaw in November 1939, he wrote letters to his wife expressing his disgust for and despair over Hitler's conduct of the war and the atrocities committed in occupied Poland. He wrote that he had become the "tool of a despotic will to destroy without regard for humanity and simple decency."
Invited by General Henning von Tresckow, Stieff joined the German resistance in summer 1943. Taking advantage of being in charge of Organisationsabteilung, he acquired and kept all sorts of explosives, including some from foreign sources. He provided the explosives for von dem Bussche's canceled assassination attempt on Hitler at the Wolfsschanze (Wolf's Lair) in November.
As one of the officers who had occasional access to Hitler, he volunteered to kill Hitler himself in a suicide attack but later backed away despite repeated requests from Tresckow and Oberst Claus von Stauffenberg to carry out the assassination.
01.02.1944: promoted to Generalmajor (20)
On 7 July 1944, during a demonstration of new uniforms to Hitler at Schloss Klessheim, a palace near Salzburg, Stieff was indisposed to trigger the bomb. Stauffenberg, therefore, decided to kill Hitler himself.
In the morning of 20 July, Stieff flew with Stauffenberg and Leutnant Werner von Haeften in the Heinkel He 111 plane provided by General Eduard Wagner from Berlin to the Wolfsschanze. In the night he was arrested and brutally interrogated under torture by the Gestapo. Stieff held out for several days against all attempts to extract the names of fellow conspirators. Ousted by the Wehrmacht, he was tried by the People's Court (Volksgerichtshof) under President Roland Freisler and sentenced to death on 8 August 1944.
At Hitler's personal request, Stieff was executed by hanging in the afternoon of that same day at Plötzensee Prison in Berlin.
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