EU foreign policy chief Kaja Kallas, a former Estonian prime minister, has been mentioned as a possible European envoy for negotiations with Russia, but her hawkish reputation and personal history complicate her candidacy. In discussing her family’s past, Kallas has noted that her mother, grandmother, and great-grandmother were among Estonians forcibly sent to Siberia by Soviet authorities in the late 1940s; her relatives endured the ordeal, but she has written that many others perished there. That background informs her approach toward Moscow, yet some view her as too partisan to serve as a neutral mediator. The article explores several potential figures for the role, including Gerhard Schröder, Angela Merkel, Alexander Stubb, and António Costa, as European leaders seek to establish dialogue with Vladimir Putin amid ongoing war in Ukraine and strain with the United States.