David Litt didn’t set out to write a depressing book.

Thanks, Obama: My Hopey, Changey White House Years (Ecco), Litt’s precisely observed account of his tenure as a presidential speechwriter, is actually a riot. But to read it is to realise all that’s been lost since his ex-boss’s departure from Washington.

On the phone awaiting a flight to New York from DC, where he’s now head writer for comedy site FunnyOrDie, Litt laughed when I told him what a downer his book was.

“It was very strange writing about the Obama years as the Trump years were beginning,” he said. “The book could serve as escapism for readers, and for me as I was writing. At the end, I tried to address whether Trump negates everything Obama tried to do. And the answer’s no. It’s a two-steps-forward-one-step-back moment. I hope readers take away that, not so long ago, politics could be inspiring, and presidents could be people you looked up to. It’s just going to take a few years to get back there.”

Inside the White House, Litt worked on many Obama speeches to Jewish audiences, including a 2011 talk to the Union of Reform Judaism that Tablet magazine branded “an exercise in schmaltz”. Litt scoffed when I reminded him of that review.

“That was a special speech for me,” he said. “With any speech, you need to keep it specific to that audience, but also broadly speak to America. Jewish audiences are no exception. What struck me is that President Obama ad-libbed a line about his daughter’s barmitzvah-party circuit into his talk. He wasn’t just paying lip service; he could really speak to a Jewish audience.”

Part of that, said Litt, came from Obama’s personal connection to the Jewish story. “When we were writing for Obama and he was speaking to a Jewish audience, we always knew he wanted to tie the story of the Jewish people, immigration, and exodus into other civil rights movements,” Litt said. “He had a great line — ‘I have a father from Kenya and a mother from Kansas, which is not your typical Jewish story’ — but the Jewish story resonated with him, and he grasped it. It’s rooted in who he is.”

Thanks, Obama never disguises Litt’s awe at working inside “the most high-pressure office building on Earth”. But it also provides a hilarious, unvarnished look at the Wernham-Hogg-like parts of the job. There’s the green ID badge (B-list) versus the blue badge (A-list). There’s the VIP bathroom vs the peons’ facilities. There’s the cramped, stuffy workspaces, albeit with excellent free snacks. Litt also lays out the concentric circles of power in the White House, as fiercely guarded as alliances in Game of Thrones.

Litt’s passion for politics has family roots. He was born in Manhattan. His parents became heavily involved in B’nei Jesurun, a high-profile Progressive synagogue in Manhattan that emphasises tikkun olam as part of its mission. “The Litts’ home was an essential part of the BJ campus as they hosted countless Hebrew School Shabbat dinners, holiday cocktail parties, and executive committee meetings,” reads a tribute page on the synagogue’s web-site. “Many of the ideas which we now consider essential elements of our mission — most notably BJ’s commitment to Liberal Judaism throughout the United States and Israel — were hatched in Sara and Andy’s living room.”

At Yale, where he graduated with a history degree in 2008, Litt joined the campus “Obama for America” chapter, and became one of the “idealists who would simply not shut up about” the candidate. After graduating, a short stint with a political-strategy firm led to his hopping aboard the hope-and-change bandwagon as a field organiser for the Obama campaign.

After Obama’s stunning 2008 victory — “the moment that changed my life”—Litt landed a gig with West Wing Writers, a well-regarded firm founded by one-time DC apparatchiks whose assignments have included a notorious $40,000 edit job on a 2009 Gordon Brown speech. Litt’s White House job followed; he was 24.

Part of Litt’s mandate was writing jokes, often enlisting Hollywood A-listers like Judd Apatow to pitch in. As the book reveals, Obama could more than keep up with his staff, often massaging their gags to work even better than the originals. The former president’s innate sense of humour and timing became evident to anyone who’s watched footage from the White House Correspondents Dinner, Washington’s annual version of a celebrity roast.

The infamous 2015 appearance of “Luther, Obama’s Anger Translator”— the actor Keegan-Michael Key, yelling furious subtexts to Obama’s measured speech — was Litt’s idea.

Trump, by contrast, uses humour as a cudgel, Litt says.

“Trump has a sense of timing, but he only deploys it to bully people. It’s so different from Obama years, where, generally speaking, the goal of a joke was to make fun of himself or stand up for people who had less power — and stand up to bullies. What Trump would term a joke is about asserting dominance.

“He doesn’t have a concept of poor taste,” Litt said. ”He only uses his lines when he wants to insult or mock someone.”

Litt and his fiancée Jacqui Kappler, a prominent character in the book, still live in Washington, DC; he works from home overseeing FunnyOrDie’s content.

“Working in the White House felt like the first chapter of my life and career, as opposed to being the climactic chapter,” he said. “It’s an experience I had, but feels totally surreal even in retrospect.”