Dan Pfeiffer thought he’d be a lawyer by now.
But since becoming a White House staffer for President Barack Obama, then the co-host of a popular political podcast, then an author, he’s been a little busy.
“I just never got to the law school part,” says the 1994 Wilmington Friends School graduate.
The former White House senior advisor continues to make his mark on Democratic politics. Well known as one of the four former Obama aides turned hosts of the Democratic-leaning Pod Save America podcast, the show brings journalists, politicians, activists and the like together for fluff-free conversations about politics. From the upcoming presidential elections to being on the cusp of war with Iran to the impeachment trial of President Donald Trump, the podcast doesn’t hold back.
Last month, Pfeiffer released his second book, Un-Trumping America: A Plan to Make America a Democracy Again (Twelve Books). His first book, Yes We (Still) Can: Politics in the Age of Obama, Twitter, and Trump, from the same publishing house, picked up right after the 2016 election, revisiting how Obama navigated the political forces that created Trump, explaining where 2016 went wrong and discussing the route Democrats should go take next.
It continues some of the themes of his first, with a deeper look at how to prevent a repeat of a Trump-style presidency.
The new book suggests Trump isn’t an aberration but rather is the logical extension of the modern Republican Party, and details how Democrats can defeat Trump in 2020. The final goal through Pfeiffer’s lens? To fix democracy itself.
Growing up in Wilmington, Pfeiffer, now 44, always had an interest in politics.
His parents, Lear and Gary Pfeiffer, instilled in him an awareness of his civic duty by involving him in family discussions on politics and taking him to the polls when they voted. Lear was a teacher at Wilmington Friends School and Gary worked for DuPont.
“We talked about [politics] at the dinner table,” he recalls.
Politics didn’t top his aspirations as he entered college at Georgetown University in Washington, D.C. But he says something changed his senior year when he interned at the Bill Clinton White House.
“They [the Clinton Administration] got me hooked on politics as a potential career,” Pfeiffer says.
Pfeiffer says he thought he’d work on political campaigns after graduating from Georgetown and before attending law school. But fate had other plans when he began working on former Vice President Al Gore’s 2000 campaign for president.
“[I wanted] to have a chance to be in a place where you can have the most impact possible, do the most good, and that is always the White House.” —Dan Pfeiffer
He thought he’d begin his trek to law school after Gore won the election, but “The Gore campaign obviously did not end that way,” he says. Gore lost to then Texas Gov. George W. Bush in a much-debated election with a lengthy Florida ballot recount.
With Gore’s loss, it became clear that Pfeiffer’s time in politics wasn’t over and he wanted to end up working on national issues in the White House.
“[I wanted] to have a chance to be in a place where you can have the most impact possible, do the most good, and that is always the White House,” he explains.
That goal seemed far-fetched, he says, especially as a Democrat during the Bush era. Between stints for Gore and Obama, Pfeiffer worked for the Democratic Governors Association and Senators Tim Johnson, Tom Daschle and Evan Bayh.
One of Obama’s first staffers, Pfeiffer worked with the former president from 2007 to 2015. After Obama moved to the Oval Office in 2008, Pfeiffer took on roles as director of communications and senior advisor.
Pfeiffer credits much of his current success to the former president, who imparted lessons including how to be a good boss, how to think strategically and how to change Washington from the ground up.
“Much of what I’ve learned in my professional life I’ve learned in the nearly 10 years I worked for President Obama,” he says.
Pfeiffer left the White House before the conclusion of Obama’s second term as the 2016 election neared. At this point, he says he felt his time in politics was over. He was moving to California to take some time off and try something new after years of working long hours.
“I believed myself to be retired from politics,” Pfeiffer says.
But as the 2016 matchup between Hillary Clinton and Donald Trump began to dominate headlines, Bill Simmons of media site The Ringer approached Pfeiffer and former Obama head speechwriter Jon Favreau to produce a podcast.
Along with Jon Lovett and Tommy Vietor, two other former Obama aides, Pfeiffer and Favreau created Keepin’ It 1600, which aired through The Ringer.
The initial plan was to cover the election, with the assumption that Clinton would ultimately win, making history as the first U.S. female president, and then end the podcast.
“That’s obviously not what happened,” Pfeiffer says.
In the wake of Trump’s victory, the four men relaunched the podcast in January 2017 as Pod Save America under new media site Crooked Media, founded by Favreau, Lovett and Vietor.
The new show’s success has produced spinoff podcasts and podcast tours; HBO filmed part of the tour for a four-part special on midterm elections in contentious states that aired prior to the 2018 midterms. Former vice president and Delaware Senator Joe Biden even appears in one episode to offer door-to-door lessons on canvassing. Crooked Media has also made a name for itself with a variety of other podcasts and its progressive Democratic lean.
“We need a better conversation about politics in this country,” says the Crooked Media website. “That’s why we launched Crooked Media — to talk about politics in a way that doesn’t make you want to throw your phone out the window— with shows and analysis and other forms of sweet, sweet content that inform, entertain, and inspire action.”
When Pfeiffer thinks about how many people know his name from Pod Save America, he laughs and says it’s weird.
“There was no plan. This is not what I envisioned; this is not what I aimed for. To say I stumbled into it would be generous,” he says.
Pod Save America is an opportunity to make politics accessible, he explains. He and his co-hosts aim to inform and entertain listeners, but also to encourage citizen involvement, whether that’s registering to vote, knocking on doors or donating money to their politician of choice.
Un-Trumping America focuses on three main points, he says: how Republicans enabled Trump after his election, how Democrats can defeat him in the 2020 election and how to end Trump-like candidates with number 45.
Unlike his first book, this one places more emphasis on the future, Pfeiffer says.
“This one is much more forward-looking,” he says. “[It’s] about where we are right now but where we need to go from here.”
While he jokes that he forgot what he signed up for with writing a second book, Pfeiffer says the process was easier the second time around since he knew what to expect.
My book “Un-Trumping America: A Plan to Make America A Democracy Again” is out today.” It’s about how we win in 2020 and what all of us can do to fix our democracy to defeat Trumpism. Thanks to everyone who pre-ordered. https://t.co/ztCHGNSUzp
— Dan Pfeiffer (@danpfeiffer) February 18, 2020
As the 2020 election nears, Pfeiffer advises everyone to figure out who their favorite candidate is and how they can help them through actions like volunteering, donating and spreading the word about who they’re supporting. He emphasizes how essential this is, especially for Democrats.
“It’s very important as a party that we recognize that no matter who our nominee is, they will be exponentially better than Donald Trump,” he says.
While Pfeiffer no longer lives in Delaware, he returns frequently to visit family.
As election season ramps up once again, Pfeiffer aims to do his part to engage voters in Delaware and nationwide with Pod Save America tours and personal work.
“We want to find every way possible we can to be helpful,” he says.
Story by Meg Ryan. Published as “PODlitically Minded” in the March 2020 issue of Delaware Today magazine.