Oskar Dirlewanger, no questions. You need to be specially kind of evil to get expelled from the Nazi party on the grounds of moral depravity.
Dirlewanger was not only a war criminal, he was also a civilian criminal of the worst kind. He was a high functioning psychopath and undeniably intelligent. To make a long story short, he was a paedophile, rapist and sadist. While he held a doctorate in the political sciences, he was so depraved that he was expelled from the Nazi party in 1934 after having been sentenced to prison from sexually molesting an underage girl.
His WWI buddy in Waffen SS, Gottlob Berger, realized that only the military could keep him in order - otherwise he would end sooner or later at the guillotine (beheading was the legal method of execution in Germany on civilian crimes until 1968), and he arranged him a place in the Legion Condor. He proved to be a completely fearless soldier.
At the beginning of World War II, Dirlewanger volunteered for the Waffen-SS. He eventually became the commander of the so-called Dirlewanger Brigade (at first designated as a battalion, later expanded to a regiment and a brigade, and eventually a division), composed originally of a small group of former poachers along with soldiers of a more conventional background. It was believed that the excellent tracking and shooting skills of the poachers could be put to constructive use in the fight against partisans. Turned out that assigning him a special unit to lead provided him to fulfill all his perversion, sadistic lusts and murderlust licentiously and in impunity.
Later, Dirlewanger's soldiers were mostly recruited from among the ever-increasing groups of German convicted criminals (civilian and military) and concentration camp inmates, eventually including mental asylum patients, homosexuals, interned Romani people, and (at the end of the war) even political prisoners sentenced for their anti-Nazi beliefs and activities.
This unit - 36th Waffen Division Dirlewanger - was completely useless as soldiers, but perfect on hunting partisans and terrorizing helpless civilians. It was described as a lunatic asylum led by its patients. Dirlewanger was so hated that other SS formations shunned the division and there was an unofficial reward in the Heer for killing Dirlewanger.
Dirlewanger was a sadistic and brutal leader, and ordered death penalties whimsically. He was also completely fearless - he was wounded in combat thirteen times. Dirlewanger's leadership "was characterized by continued alcohol abuse, looting, sadistic atrocities, rape, and murder”—and his mentor Berger tolerated this behaviour, as did Himmler, who so urgently needed men such as the Sonderkommando Dirlewanger.
Finally karma caught him. Dirlewanger was arrested on 1 June 1945 near the town of Altshausen while he was wearing civilian clothes, using a false name and hiding in a remote hunting lodge. He was recognised by a Jewish former concentration camp inmate and brought to a detention centre. He reportedly died around 5–7 June 1945 in a prison camp at Altshausen - he was gang-upped by Polish inmates and clubbed to death.
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