While working toward his doctorate and amid the unraveling fabric of the Soviet power structure, Medvedev joined Sobchak in his campaign for the USSR Congress of People’s Deputies. Sobchak, often cited as one of the earliest voices advocating free markets and political pluralism, advocated these positions in his campaign and drew the ire of KGB agents who confiscated his campaign literature.

Medvedev and others stayed up late into the night to print another set by hand, according to Sobchak’s widow, Larisa Narusova. Sobchak easily won the election. Medvedev remained close to Sobchak as he, one of the few deputies with a legal background, set about creating many of the laws that would provide the foundation of a post-Soviet Russia.

For his part, Medvedev published the first of several law textbooks, an award-winning volume on the Russian civil code that was first published in 1991. From 1990 to 1999, Medvedev maintained a private practice in law, co-founded or advised several businesses and worked in government. Interviews with those familiar with Medvedev at the time describe his role as a go-between for government officials and business leaders, a legwork man with a deep knowledge of the legal structure.

Sobchak was elected to the Leningrad City Council in 1990 where he helped overhaul the structure of city politics and mandate a general election for the mayoral position. When the first elections were held in June 1991, Sobchak was on the ticket and he won handily. Medvedev went to work again for his former professor in the city government. He served as a legal adviser to Sobchak and a legal consultant to the committee for external affairs – headed by Vladimir Putin.

Putin and Medvedev worked together closely for years. As Sobchak busied himself writing the constitution of the Russian Federation and laying the legal foundation for the new government, running the city fell to deputies like Putin. A city council member at the time said Putin made the decisions while Medvedev did the legwork. Putin sold off city property and liaised with foreign officials. Medvedev provided legal advice, extended his private interests and continued to teach law at his alma mater. They remained with city government until 1996 when a former deputy, Vladimir Yakovlev, ran against Sobchak riding a wave of corruption charges and ousted him from office.

From the time he graduated from the law school, Medvedev maintained a double life in business and politics. In 1990, he co-founded a small, state-controlled company called Uran. Four years later, he co-founded a consultancy group called Balfort. Both companies were founded with his classmates from Leningrad State University (now St. Petersburg State University).

In 1993, Medvedev joined Ilim Pulp company as legal affairs director where he helped turn the paper-processing company into a multi-million dollar industry leader. There, he used a connection to former KGB and military intelligence officers to help fight off a hostile takeover attempt of the lumber company. He resigned from his position at Ilim Pulp at the same time as government officials started looking into the company’s privatization projects, according to a biography published on lenta.ru.

Medvedev also co-founded Fintsell, a holding company with a stake in Ilim Pulp. In 1998, he took a position as chairman of the board of directors of Bratsky Forestry Complex. He also worked as a consultant for the insurance company, Rus’, under Vladislav Reznik, who later went on to head the State Duma’s committee on credit organizations and financial markets.