Sharing a joke with the President ahead of Paris fashion week, 2012. Pete Souza /

By Tom Dare

A NEW BOOK by the deputy chief of staff during Barack Obama’s Presidency has given a fascinating and intimate insight into life in the White House pre-Donald Trump.

Pictures from ‘Who Thought This was a Good Idea’ show President Obama laughing and joking with author Alyssa Mastromonaco in the White House, while others show Mastromonaco sharing a high-five with then First Lady Michelle Obama.

The President takes a call on Air Force One with Alyssa. Pete Souza /

Other images show a stern-looking Obama sitting on the arm of Mastromonaco’s chair on Air Force One, with further images show the president taking a phone call while sat next to his deputy chief of staff.

Mastromonaco worked for Obama for ten years, taking up the position of director of scheduling in 2004 and working her way up the ranks to eventually be given the title of deputy chief-of-staff before leaving his administration in 2014.

One of Mastromonaco’s main roles during her time working with Obama was to write his schedule, from meetings with senior military strategists to a visit to meet the Pope.

Alyssa swaps a high five with first lady Michelle Obama at a reception for her leaving drinks in 2014. Pete Souza /

And in ‘Who Thought This was a Good Idea’, Mastromonaco gives an insightful and often witty account of her approach to top-level politics.

“When you see my life on paper, it’s not remotely obvious how I would end up, at age 32, working as the right-hand woman to the first African American president, sitting across from him on Air Force One heading to Afghanistan, Russia, China – or, honestly, anywhere,” she writes.

“A lot of people ask me how a public school kid from Upstate New York with no connections and no Ivy League acceptance letters, who spent more time at God Street Wine shows than in academic club meetings, ended up a few feet from the Oval Office, working as one of the youngest women ever to be a deputy chief of staff for the president of the United States.

Deep in thought with President Obama. Pete Souza /

“Sometimes these people are being rude, like, How could someone like you end up in a job like that? Sometimes they’re genuinely curious. Sometimes they want to know so they can do it, too.

“I wanted to write this book to try to answer the question for everyone, but especially the last group. (The jerks are least important to me, but they can still eat it.)

“I have come to believe that hard work and a good attitude can get you further than you could ever dream, and unfortunately, this is a really basic lesson that doesn’t come up in most career advice. It’s kind of cheesy, but sometimes life is cheesy for a reason.”

After being told she was the size of a hedgehog, Alyssa demonstrates her best hedgehog impression to the President, senior adviser Daniel Pfeiffer and White House Press Secretary Jay Carney. Pete Souza /

‘Who Thought This was a Good Idea’ by Alyssa Mastromonaco is published by Little, Brown books, and is available on Amazon here: