Trajkovski's rise to power has been extremely rapid. He first entered politics in 1997, when he was the top official in the mayor's office in the Kisela Voda Municipality (1997–98). In 1999 he served as deputy minister of foreign affairs. He has also been chairman of the ruling VMRO-DPMNE party's foreign relations commission and served as the chief political adviser on foreign policy to Prime Minister Georgievski. In the fall of 1999, Trajkovski ran for the presidency as the IMRO-DPMNV's candidate. He was elected in November 1999 and sworn into office in December. The opposition Social Democratic Union charged electoral fraud, and Organization on Security and Cooperation in Europe (OSCE) observers noted some irregularities, primarily in majority-Albanian areas. They termed the overall election process fair and legitimate, however.