Path to Power
Raised by his father who was a professor of sociology at the University of South Dakota and his mother who taught 5th graders, Stewart had an early introduction to politics. One of his best friends as a child was the son of now-Sen. Tim Johnson (D-S.D.). Johnson worked in the South Dakota House of Representatives at the time, but the connection to the future senator would prove fruitful for Stewart.
For college, Stewart attended the University of South Dakota where he studied biology and chemistry. After graduating in 1999, Stewart joined Sen. Johnson’s offices in Sioux Falls, S.D. He would stay in Johnson’s South Dakota offices for a year before heading to Washington to work for the senator.
Stewart worked on Capitol Hill for two more years, and then returned to South Dakota to help with Johnson’s re-election efforts. In 2002, Johnson was facing a young, up-and-coming Republican, then-Rep. John Thune. President George W. Bush was extremely popular at the time, and he visited South Dakota five times during the 2002 campaign to support Thune. Stewart worked as a regional field director, helping Johnson eke out a victory by less than 530 votes.
After the successful Johnson campaign, Stewart found a new passion: elections. He immediately followed the Johnson campaign by heading down to Louisiana to aid Sen. Mary Landrieu’s (D) re-election efforts as she faced a runoff after failing to gain a majority in the general election.
Landrieu successfully won her re-election bid, and Stewart began work on the 2004 presidential race. He headed to Cedar Rapids, Iowa, to work as a regional field director for presidential candidate and former Sen. John Edwards (D-N.C.). Although Edwards fared well, Sen. John F. Kerry (D-Mass.) won the Iowa caucuses and used the momentum to secure the Democratic nod. But by that time, Stewart had already headed back to South Dakota as a fierce fight for a Senate seat was beginning to shape.
Senate Minority Leader Tom Daschle (D) was up for re-election in 2004, trying to beat back Thune, who had been energized in 2002 after nearly knocking off Johnson. Daschle took hits as Thune painted the minority leader as an obstructionist. Thune won the election, marking the first time a sitting party leader had lost a re-election bid since 1952.
After the disappointing loss in South Dakota, Stewart moved to the D.C. based, Environmental Defense Fund as national field director. He assisted the non-profit in its climate change campaign. Stewart stayed a year before becoming the Minnesota director for the Democratic-Farmer-Labor party.
2008 Obama Campaign
But Stewart didn’t stay in Minnesota for long. In 2006, he joined the Obama campaign as a caucus director in Iowa. Supervising the opening of over 35 local offices, Stewart helped build support for the unknown senator from Illinois. It worked. Obama easily won the Iowa caucuses. After Iowa, Stewart spent short stints campaigning for Obama in Nevada, Minnesota, Texas and Indiana.
The success Stewart helped achieve in Iowa earned him a spot in the general election as Obama’s state director in the key state of Virginia. The state had not gone for a Democratic presidential candidate in 44 years. But with the help of Gov. Tim Kaine (D) (who is now Democratic National Committee chairman), Stewart orchestrated a winning strategy. On election night, Virginia went to Obama with a 53 percent majority.