VINEYARD HAVEN, Mass. — Even on a summer family vacation, President Barack Obama is followed by an entourage whose behind-the-scenes movements are juggled by a woman who was born into politics and has been with him since his Chicago days.

Ashley Tate-Gilmore heads the White House Travel Office, a five-person operation that handles precise logistics behind every presidential trip. The details usually go unnoticed by the public, unless something goes horribly wrong.

Tate-Gilmore not only acts as a high-stakes travel agent for White House press and staff but also as a mini-ambassador who is often the first to arrive at presidential destinations.

She’s used to being underestimated, a 29-year-old woman who is quick to laugh and signs off every email with a smiley face. She said it was clear from her first meeting with foreign officials when she took over the job three years ago that they weren’t expecting to take directions from a woman who looks so young.

“People are, like, ‘Who are we meeting with?’ I was, like, ‘Me.’ And mouths dropped,” she said in a recent interview.


Highly organized


But anyone who thinks Tate-Gilmore is just a sweet young thing is in for a surprise. She was raised in the rough-and-tumble world of Chicago politics. Her mother got pregnant while working on Harold Washington’s campaign to become the city’s first black mayor and raised her daughter as a single parent on the city’s South Side with help from her own mother.

By Washington’s re-election campaign, little Ashley was coming along to help. “At 4 years old, Ashley was stuffing envelopes,” said her mother, Desiree Tate.

Tate-Gilmore lives out of a bag and her job requires that she be highly organized and think on her feet as she juggles planning for multiple White House trips. A recent eight-day vacation to Martha’s Vineyard required her to help set up a White House operation on the island at peak season, when accommodations are hard to find. She helped reserve rooms for media, staff, Secret Service agents and others supporting the presidential operation in so many places across the island that she’s lost count — booking rental homes and even a trailer for staff to work out of when there were no more hotel rooms to be had.


Media entourage


Meanwhile, from the island she was dealing with visa applications for Obama’s visit to Russia earlier this month and setting up Obama’s bus tour last month to New York and Pennsylvania.

Tate-Gilmore has learned to be no-nonsense in her dealings with local officials, hotels and venues Obama will visit. In preparation for his trip to Africa earlier this year, members of the White House advance party suffered bug bites staying in the press hotel. Tate-Gilmore demanded the hotel hire an exterminator — and take along a photographer who could email her pictures back in Washington to prove all the rooms had been fumigated. When a radio reporter contracted food poisoning on the stop in Tanzania, Tate-Gilmore insisted on staying overnight in the hospital and worked with doctors to ensure she got proper care.

Reporters, photographers and others with the news media pay their share of expenses when they accompany the president. In recent years, the size of the media entourage has dropped as some outlets have determined that the tab is just too high. With media outlets feeling increasing financial pressure, controlling costs is a big part of Tate-Gilmore’s job as she weighs fees for rooms and travel.

“The kind of glitz and glamour that people think we bring with the White House — they will roll us if they can,” Tate-Gilmore said.


Presidential events


But costs are not the only consideration. The White House has to deal with security and access issues, as well, for its press corps. If reporters were left to travel commercially on their own, they would never be able to keep up with Air Force One flying around the globe and get in and out of the president’s security bubble.

The press charters a plane that mimics Air Force One’s route. Reporters and news crews stay in hotels accessible to presidential events. And they ride in buses that often have police or military escorts to whisk them through security checkpoints. All the costs are covered by the traveling media but the arrangements are coordinated by the White House Travel Office, as under previous presidents.

Tate-Gilmore volunteered on Obama’s U.S. Senate campaign in 2003 while home in Chicago from a break as a psychology student at Howard University. Soon she was hired for a paid position managing other volunteers. After Obama’s election, she was one of the first hires in his Senate office and eventually worked as his executive assistant.

When Obama moved to the White House, Tate-Gilmore went along as an associate manager in the Travel Office under director Peter Newell, who said he recommend her to take over when he left in September 2010. He said her experience with the president, her knowledge of press travel and her relationships throughout the White House made her up to the task even though she was 26 at the time.

“What the job required, Ashley had,” Newell said. “You need to be a people person and be able to be friendly. Ashley is good at engaging people and she has a great sense of humor. But she also has a firm backbone and she can be tough.”