After Sobchak’s loss in the mayoral race in 1996, Putin had gone to Moscow. Medvedev remained behind in St. Petersburg where he taught and pursued his business interests. President Boris Yeltsin appointed Putin as prime minister in August 1999 and tapped him as his preferred successor. Putin summoned Medvedev to Moscow to head the government administration in November 1999. One month later, Yeltsin resigned and Putin brought Medvedev along as deputy head of the presidential administration. During presidential elections in 2000, Medvedev was the head of Putin’s campaign.

Medvedev was one of several St. Petersburg colleagues whom Putin moved to Moscow, and his rise through the echelons of government was – like Putin’s – meteoric. While in the presidential administration, Medvedev avoided an affinity with either of two poles of power forming in the Kremlin: the camp of security service officials (known as the “siloviki”) or the group around Alexander Voloshin, Putin’s chief of staff and one of the major figures of the Yeltsin-era “family.” When Voloshin resigned in the October 2003, he was replaced by Medvedev.

From 2001 to 2003, besides his day to day responsibilities in the Kremlin staff supporting the president’s activities, he was assigned to special projects. This included heading the commission which oversaw the drafting and enactment of framework legislation on the reform of the civil service and looking at ways to best overhaul the judicial system.

In 2000, Medvedev became chairman of the board of directors at the state-controlled gas monopoly, Gazprom. He was the board’s deputy chairman from 2001 to 2002 before resuming the chairmanship.

He was head of Gazprom when Gazprom Media took control of the flagship holding in Vladimir Gusinsky’s media empire, the NTV television channel. Under Medvedev’s management, Gazprom considered a merger with Rosneft, a company that bought most of Yukos’s assests in an auction arranged by the state as a way for Yukos to pay off its tax bill. However, Medvedev made no politically charged statements against Mikhail Khodorkovsky and other disgruntled oligarchs. He insisted that such auctions were the only “legally effective” means to recover back taxes. From 2005 to 2007, with Medvedev at the helm, Gazprom was at the center of the “gas wars” with Ukraine and Belarus.

For most of his professional career, Medvedev had been a behind-the-scenes player, known mostly to those paying attention as a business leader and behind-the-scenes government player. That all changed in November 2005, when Putin appointed Medvedev to a specially created post as first deputy prime minister in charge of five national projects. Two months earlier, Putin had outlined the national projects which focused on domestic development. Medvedev took the lead and the national projects garnered enormous media attention on state-run television.