Alyssa Mastromonaco

Why She Matters During the 2008 campaign, Mastromonaco took great pride in ensuring Barack Obama was in the right place at the right time. “The greatest commodity on the campaign is his time,” she said.(1) Mastromonaco was Obama’s director of scheduling and advance for the campaign, and she will hold the same title in his White House. Mastromonaco’s job won’t get an easier as she moves to 1600 Pennsylvania Avenue, but now she can book her boss on Air Force One. A political veteran who worked as Sen. John F. Kerry’s (D-Mass.) director of scheduling during his presidential run, Mastromonaco was one of the first people Obama hired to join his senate office in 2005. She has been a part of his inner circle and was, literally, in the room when Obama decided to run for president. Since then, her job has gotten increasingly hectic as she tried to juggle campaign stops in important states with Senate votes and family time. Mastromonaco is a logistics expert, but she also served as political director of Hopefund, Obama’s leadership political action committee, and worked on policy, strategy and financial decisions during the 2008 campaign. In the White House, Mastromonaco will head a team of 35 employees who are responsible for Obama’s every move. Path to Power Mastromonaco grew up in upstate New York and was not particularly interested in politics, though she said she organized her first event in nursery school. She divvied up tasks (cupcakes, balloons, streamers) to her fellow 4-year-olds for a party for one of her teachers. “The teachers scolded me for organizing a rogue party,” she said. “But I had all my bases covered.”(2) During her sophomore year at the University of Vermont, an adviser suggested she intern for then-Rep. Bernie Sanders (I-Vt.), who later became a senator. Mastromonaco worked from Burlington, Vt., and then spent a summer at his Washington office. That convinced her to switch her major from French to political science and transfer to the University of Wisconsin-Madison.(3) After a brief stint in real estate, Mastromonaco worked for two years in Kerry’s Boston office. She said it took a pleading letter and three interviews to get the entry-level job, but she quickly worked her way up the ladder.(2) She worked as both deputy press secretary and deputy scheduler for Kerry and then took a job with the American Beverage Institute as director of membership. She worked there for just six months before being lured back to Capitol Hill.(4) In July 2002, Mastromonaco became press secretary for Rep. Rick Boucher (D-Va.). But when Kerry launched his presidential bid in 2003, Mastromonaco left Boucher's office and signed on as Kerry's scheduler.(4) She organized his trips and campaign appearances, worked with potential vice presidential candidates to arrange secret meetings and made sure Kerry made his votes in the Senate. After Kerry lost, Mastromonaco began looking for a new job, saying that she wanted to work for someone who was not going to be running for president.(5) She made the wrong choice. She joined Obama’s office as director of scheduling in early 2005, just after he was elected to the Senate.(6) Even before he was running for president, Obama was a political star and had a busy schedule full of book tours and campaign stops. Mastromonaco became one of the popular official’s closest advisers. She was one of the few people in the room when Obama decided to launch his campaign. To help the Obamas weigh their options, she drew up a sample three-month schedule for them to look at and consider.(7) For the next two years, Mastromonaco employed her logistical skills to organize all of Obama’s flights and campaign stops. She also served as political director of Obama’s leadership PAC, Hopefund. When he won, Obama brought her to the White House as an adviser and scheduler. The Issues During the campaign, Mastromonaco worked with Obama and other senior advisers to coordinate campaign stops and Senate votes. She’s an expert at rattling off the length of runways at small rural airports and the time it takes to travel between two cities.(8) “I just always like knowing that the planes are taking off and landing, and the cars are where they need to be, and that people have briefing materials, and when that all happens, I sleep easy,” Mastromonaco said.(9) She helped to schedule Obama’s much-needed pick-up basketball games and family time during the campaign. She also organized Obama’s overseas trip in July 2008, working with eight advance teams and setting up 15 events in five countries. She squeezed Obama into as many television markets as possible during the 10 days between the South Carolina presidential primary and Super Tuesday, a feat campaign manager David Plouffe described as “a thing of beauty.”(2) Mastromonaco also coordinated with Michelle Obama’s schedule and fit family time in for the busy candidate. It’s a job that allows little room for error — Mastromonaco told Glamour that her biggest mistake was booking a plane for Obama for the wrong day.(10) The Network Mastromonaco became interested in politics after interning for Sen. Bernie Sanders (I-Vt.) when he was a member of the U.S. House. She worked for Sen. John F. Kerry (D-Mass.) during his presidential campaign in 2004 and is a member of Obama’s inner circle. Footnotes 1. Chris Wallace, “Power player of the week: Alyssa Mastromonaco,” Fox News Network, March 18, 2007 2. Murray, Shailagh, “It’s about time,” The Washington Post, Dec. 22, 2008 3. Brian Tumulty, “Rhinebeck woman to serve as White House scheduler,” Gannett News Service, Nov. 28, 2008 4. Daphne Retter, “People on the move,” Congressional Quarterly Daily Monitor, July 18, 2002 5. Leah Chernikoff, “Obama woman. Forget the girl – here’s Barack’s female A-list,” New York Daily News, June 19, 2008 6. Press release, “Alyssa Mastromonaco named White House Director of Scheduling and Advance” 7. Evan Thomas, “How he did it; A team of Newsweek reporters reveals the secret battles and private fears behind an epic election,” Newsweek, Nov. 17, 2008 8. John McCormick, “Chicago is heart, brain center of Obama campaign; Key operatives steer presidential bid,” Chicago Tribune, June 11, 2007 9. Chris Wallace, “Power player of the week: Alyssa Mastromonaco,” Fox News Network, March 18, 2007 10. Linda Kramer Jenning, “How to love a crazy job,” Glamour, Dec. 1, 2007