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His father of the same name, a doctor of law, had worked as a diplomat in the German Empire and then as an in-house counsel for business associations. At the age of 17, settlers were drafted into military service for National Socialist Germany as air force helpers. Because of the alleged "undermining of military strength", the young settler received a prison sentence of several months, after which he was sent to the front and became a prisoner of war. After graduating from high school, Siedler began studying sociology, history, philosophy and German studies in 1948, initially at the Humboldt University in Berlin. A year later he moved to the newly founded Free University in the western part of the four-sector city. However, Siedler soon dropped out of his studies without completing his studies.
Instead, he was involved in the Berlin Germany office of the "Congress for Cultural Freedom", of which he was general secretary from 1953 to 1956. In 1954 he joined the "Neue Zeitung", where he worked as a features editor until 1955. Following this, Siedler was appointed to the editorial team of the Berlin "Tagesspiegel" as features editor. In 1963, the journalist moved to the Ullstein publishing group, where he headed the "Propyläen-Verlag" from then on. Here Siedler was responsible for such renowned major projects as the continuation of the "Propylaea World History" in 12 volumes as well as the initiation of the "Art History" of the same name in 23 and the "Europe" History in six volumes. In 1967, Siedler also became managing director of "Verlag Ullstein GmbH". He headed the publishing group until 1979. At the beginning of 1980, Siedler took the step into independence by founding the publishing houses "Severin und Siedler" and "Quadriga" in Berlin with the film producer Jochen Severin.
The publishing program focused on historical and contemporary publications, the demanding level of which soon brought the company success. After Severin's departure, who had transferred his shares to "Bertelsmann AG", the company was converted into "Wolf Jobst Siedler Verlag GmbH" in 1983, in which "Bertelsmann" initially held a quarter of the shares. The publishing director and managing partner continued the company's demanding publishing program in the following decades. In addition to the complete edition of the estate of the first Chancellor of the Federal Republic, Konrad Adenauer, the memoirs of important statesmen from home and abroad - including Helmut Schmidt, Franz Josef Strauß, Hans Dietrich Genscher, Mikhail Gorbachev and Boris Yeltsin - were among the most committed projects of the "Siedler Verlag".
Large-scale historical projects on German history as well as individual publications on contemporary historical issues rounded off the publishing program. In 1996, Siedler rekindled the public debate about the German population's involvement in the Holocaust with the publication of the German translation of Daniel J. Goldhagen's book about "Hitler's Willing Executors." Even after Siedler had transferred his remaining shares to "Bertelsmann AG" in 1993, which has since become the sole owner of the publishing house, he continued to manage the company until 1998. In the same year, "Siedler Verlag" was merged with "Berlin Verlag" and placed under the management of Arnulf Conradi. Since then, Siedler has remained associated with the publisher as editor of the history series. He also worked as a freelance journalist for several newspapers; including the FAZ, the Süddeutsche Zeitung, Die Zeit, DIE WELT and the Berliner Morgenpost.
Siedler has been honored with several publishing and journalism awards. In 1984 he received the "Karl Friedrich Schinkel Ring" and in 1987 he was awarded the "Ernst Robert Curtius Prize for Essays". In the same year he also received the Federal Cross of Merit, First Class, which was followed by the Grand Federal Cross of Merit with Star in 1995. The History Department of the Philosophical Faculty of the Free University of Berlin awarded Siedler an honorary doctorate in 1996. Towards the end of 2001, together with the writer Günter de Bruyn, he received the "National Prize of the German National Foundation in Weimar". In 2007 he was honored with the "Gerhard Löwenthal Prize".
