Craighead grew up in Connecticut, where her parents owned a photo lab, introducing her to photography at a very young age.
Craighead was the photographer for first lady Laura Bush during the George W. Bush administration.
As part of her job photographing the first lady during the Bush administration, she also had the opportunity to capture the wedding of the president's daughter, Jenna Bush, who married Henry Hager in 2008.
"Being Governor Palin’s photographer really propelled me into the next level of political photography," Craighead told Marie Claire.
Craighead joined the Donald Trump administration as chief White House photographer shortly before the inauguration in 2017. Since then, she has followed Trump everywhere.
The White House photographer gets considerably more access than the press corps, giving her an up-close and personal view of the president at some of his most historic moments during his time in office.
"I’m very honored to be in this spot, that’s for certain," Craighead told Marie Claire in an interview. "I think that anybody — male or female — in this position, it’s a real honor."
The only other female to serve in her role was Sharon Farmer during the Bill Clinton administration.
"As I went through college and life I also realized I had always wanted to do something that involved traveling the world and living in hotels," Craighead told PBS NewsHour. "And that involved photography."
Craighead told PBS NewsHour in an interview she often uses a small stool while taking photos, citing her short stature.
"So that I’m not photographing from the ground up but sky down. I’ve brought that into the White House as well, because the president is six-foot, and I’m five-two."
"In the White House, you’re not just documenting history, you’re also putting other caps on," she told PBS. "You’re an event photographer, an operations director — establishing where the team should be to get all the angles. You’re a documentary photographer, you’re a family photographer, you shoot portraits. If the president is athletic, or doing sports, you’re a sports photographer too."
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