"We would stop in all these small towns and we would have all these little gatherings," Breckenridge recalled.
This month, Obama and Breckenridge came to Martha's Vineyard, the president's vacation spot, riding face to face in a convoy of helicopters.
It has been no vacation for her.
Breckenridge has coordinated with the Secret Service for coverage at Obama's rented home, on the golf course or wherever else he decides to unwind. Between Obama family outings to the beach and the president's dinner dates with the first lady, she works into his schedule staff briefings and calls with foreign leaders.
She decides when to interrupt his leisure with updates on emerging problems, such as the airstrikes in Iraq and the unrest in Missouri.
When Hillary Rodham Clinton wanted to smooth over critical comments she had made about Obama's foreign policy, the former secretary of state emailed Breckenridge to set up a call.
Back in Washington, the 36-year-old is responsible for presidential staff and political appointments, Obama's schedule, the advance work of setting up any of his movements and the general nuts and bolts of how Obama's White House functions.
"His day is organized by Anita, so she's making sure he's seeing people he wants to see," said senior Obama adviser Valerie Jarrett. "She has a thousand balls up in the air at one time. It takes an extraordinarily high level of skill, but it also takes a good sense of him and what's important to him."
Obama chose Breckenridge as deputy chief of staff for operations when longtime aide Alyssa Mastromonaco left last spring.
In some ways, Breckenridge was an unusual pick for a post with such an expansive portfolio. She was viewed as a friendly and efficient gateway to Obama outside the Oval Office but not as an aggressive operator. Also, she wasn't well known outside the West Wing.
Breckenridge had management experience as chief of staff of the National Endowment for the Arts in Obama's first term and ran his downstate offices in Illinois when he was senator. But her chief qualification for the new post was her close relationship with the president.
She's proved to be fiercely protective of his personal needs and quick to turn away those she feels are trying to demand too much of him. Her position requires her to channel his wishes as she makes a lot of rapid-fire decisions on his behalf.
"It's hard for me to come up with anyone else the president trusts so implicitly," Mastromonaco said. "They have known each other for so long, their relationship is homegrown. Anita understands everything he needs and wants to know."
Breckenridge, a native of the Chicago suburb of Kenilworth, also provides familiarity to Obama at a time when many of his most trusted aides are leaving. She's Obama's link to a humbler time when he grows weary of the White House trappings.