Ilves worked as a research assistant in Columbia University Department of Psychology from 1973 to 1979. From 1979 to 1981 he served as assistant director and English teacher at the Open Education Center in
Englewood, New Jersey. and from 1983 to 1985, he taught Estonian literature and linguistics at
Simon Fraser University. also serving as Ambassador to Canada and Mexico at the same time. As a condition for the job, he had to renounce his US citizenship. In December 1996, Ilves became
Estonian Minister of Foreign Affairs, serving until he resigned in September 1998, when he became a member of a small opposition party (Peasants' Party, agrarian-conservative). Ilves was soon elected chairman of the People's Party (reformed Peasants' Party), which formed an electoral cartel with the
Moderates, a centrist party. After the
March 1999 parliamentary election he became foreign minister again, serving until 2002, when the so-called Triple Alliance collapsed. He supported Estonian membership in the
European Union and succeeded in starting the negotiations which led to Estonia joining the European Union on 1 May 2004. From 2001 to 2002 he was the leader of the People's Party Moderates. He resigned from the position after the party's defeat in the October 2002 municipal elections, in which the party received only 4.4% of the total votes nationwide. In early 2004, the Moderates party renamed itself the
Estonian Social Democratic Party. In 2003, Ilves became an observer member of the
European Parliament and, on 1 May 2004, a full member. In the 2004 elections to the European Parliament, Ilves was elected
MEP in a landslide victory for the Estonian Social Democratic Party. He sat with the
Party of European Socialists group in the Parliament.
Katrin Saks took over his MEP seat when Ilves became President of Estonia in 2006. In 2011, he was re-elected for a second five-year term. In 2013, it was announced that Ilves had accepted a position on the Council on CyberSecurity's Advisory Board. In 2015, it was announced that Ilves had agreed to join the group of advisers to the World Bank president
Jim Yong Kim. During his presidency, Ilves has been appointed to serve in several high positions in the field of ICT in the European Union. He served as chairman of the EU Task Force on eHealth from 2011 to 2012 and was chairman of the European Cloud Partnership Steering Board at the invitation of the
European Commission from 2012 to 2014. In 2013 he chaired the High-Level Panel on Global Internet Cooperation and Governance Mechanisms convened by
ICANN. From 2014 to 2015 Ilves was the co-chair of the advisory panel of the
World Bank's
World Development Report 2016 "Digital Dividends" and was also the chair of
World Economic Forum's Global Agenda Council on Cyber Security beginning in June 2014. Beginning in 2016, Ilves has been co-chairing The
World Economic Forum working group
The Global Futures Council on Blockchain Technology. In 2017 he joined
Stanford University as a Bernard and Susan Liautaud Visiting Fellow at the
Center for International Security and Cooperation in the
Freeman Spogli Institute for International Studies. From July 2017, Ilves has been a Distinguished Visiting Fellow at the
Hoover Institution, Stanford University. In 2017, Ilves joined the advisory council of the
German Marshall Fund's
Alliance for Securing Democracy, a project aimed to map out the Russian influence activities in the USA and the EU. On 25 September 2020, Ilves was named as one of the 25 members of the "Real Facebook Oversight Board", an independent monitoring group unaffiliated with, but created in response to, the
Oversight Board,
Facebook Inc.'s content moderation review board. In 2024, Ilves was the subject of a documentary,
Rebel with a Bow Tie (Estonian:
Kikilipsuga Mässaja), directed by filmmaker
Jaan Tootsen, who was formerly Ilves's cultural advisor during his presidency. The film debuted at the 28th
Tallinn Black Nights Film Festival on 15 November 2024. After almost 20 years as a non-party politician, Ilves has been a
Volt Europa party member since April 2025. He explains the change by the increasing threat posed by other countries to Europe and the need for pragmatic reforms in the European Parliament. ==Presidential elections==