By early 1944 , Kappler was the highest representative of the Reich Main Security Office in Rome and answered directly to both the military governorship , under Luftwaffe General Kurt Mälzer , as well as the SS chain of command under the Higher SS and Police Leader of Italy , SS - '' Obergruppenführer '' Karl Wolff . Kappler came into direct conflict with the Vatican , as the Germans had strong suspicions that it was harbouring Allied fugitives and escaped prisoners , even though the Vatican under Pope Pius XII was technically neutral . A particular adversary of Kappler 's in this respect was Monsignor Hugh O'Flaherty , whose activities helping Jewish fugitives and Allied prisoners escape from Rome led to Kappler having him targeted for assassination . Paradoxically , after the war Kappler and O'Flaherty would become friends of sorts . Kappler organised the Ardeatine massacre where 335 Italian civilians were killed on 24 March 1944 as a reprisal for an attack by resistance fighters resulting in the deaths of 33 men of the SS Police garrison in Rome
Ardeatine massacre
Ardeatine massacre
Herbert Kappler