Wilhelmine Germany had a powerful economy and, after 1898, began construction of a fleet to challenge Great Britain's global power. This article analyses Germany's cultural "will to power" in the period through the eyes of the avant-garde, Munich-published weekly magazine Simplicissimus as it examined the series of security crises between 1896 and the outbreak of war in 1914. The magazine was no fan of Wilhelmine militarism, its principal artist having been jailed for criticism of the kaiser, but it showed a deep support for Germany's rise to power on moral grounds. Many illustrations dealt with global power projection through the navy and the need for a suitable security partner within Europe. Its illustrators depicted Great Britain as an immoral world power only Germany might check and France as its preferred security partner to keep Europe at peace. Keywords: cultural will to power, naval power, security partners, Simplicissimus, Wilhelmine Germany.