Then John became chairman of Hillary Clinton's 2016 presidential campaign, putting the Podestas in the crosshairs of the alt-right. In the middle of the campaign, John's hacked emails led to "Pizzagate," a bizarre conspiracy theory about a child sex ring. Finally, and against all expectations, his candidate lost the bitterly fought election.
Now Tony's work for a Ukrainian nonprofit group is part of special counsel Robert S. Mueller III's Russia investigation, prompting the powerful lobbyist to resign from the Podesta Group, the firm he founded three decades ago.
"I didn't leave with a sense of tragedy or regret about anything I had done," Tony said nonchalantly in an interview last week. "I thought it was better for the clients and better for the people in the office for me to get out of there."
His bravado notwithstanding, it's been a really bad year for the Podesta brothers, even by the standards of political hand-to-hand combat.
They've become a particular fixation for President Trump, who has repeatedly attacked the two in tweets and interviews. On the eve of his current trip to Asia, he told reporters he was "disappointed" that the Justice Department was not investigating Hillary Clinton and her advisers instead of him: "Honestly, they should be looking at the Democrats, they should be looking at Podesta and all of that dishonesty."
Meanwhile, Fox News is calling the Podesta brothers "central figures" in the Mueller probe.
One might expect Tony Podesta to be angry — and apprehensive — about all this, and maybe he is. But at the moment, he's smiling and cracking jokes.
"There was a period when I was at People for the American Way in which I was the devil, and this is another period in which I am the devil," he says. "I don't retreat from my values or my life because Tucker Carlson makes s--- up."
And he's laughing off the president.
"If you tweet 'Podesta' you get some applause from people who don't know who we are or what we do," he says. "He has his phone. And I have my integrity."
For all the talk about the Podestas being Washington insiders — and they absolutely are — the irony is that they grew up as far from elite as possible.
They were born in working-class Chicago to two first-generation Americans: their father Italian, their mother Greek, the family living in a "two flat," with their aunt, uncle and cousins in the apartment upstairs. Their father worked factory jobs and lost sleep worrying about the $11,000 he borrowed to buy the apartment, Tony says. Tony attended the University of Illinois at Chicago; John went to Knox College.
From this background, colored by the Vietnam War and the political upheavals of the 1960s and '70s, emerged two men with a shared passion for liberal issues and a weakness for losing candidates: They worked for Gene McCarthy, Edmund Muskie, George McGovern and many more. "We weren't doing it to go to the White House," Tony says. "We were doing it because we believed in what we were doing."
The two made their way to Washington, where they both attended law school at Georgetown University, worked briefly in government, then founded the Podesta Group in 1987. Their paths quickly diverged: Tony working outside politics, lobbying, fundraising and serving as president of People for the American Way, the progressive advocacy group founded by TV producer Norman Lear; John on the inside, in the Clinton and Obama administrations and as head of the Center for American Progress, the premier liberal think tank during the George W. Bush years.
The two brothers, who are very close, became power brokers on a first-name basis with every important figure in American progressive politics, and many across the aisle. Every call they made was answered, every door they knocked on opened.
Tony, 74, is expansive, expressive, a happy warrior. "He's partisan in the traditional way, which is rapidly disappearing in Washington," says longtime Republican lobbyist Wayne Berman. "He understands the value of having friends on the other side. It's a happy partisanship, not a bitter partisanship."
He wears red Prada loafers and owns one of the capital's most impressive modern art collections, which serves as the backdrop for the frequent parties he hosts at his Kalorama mansion. The collection began when he worked for the failed 1980 presidential bid of Sen. Edward M. Kennedy (D-Mass.) and walked away with a tube of donated art — limited editions of Andy Warhol and Robert Rauschenberg — in lieu of a salary.
Always well known in political circles, Tony became a celebrity with his high-profile second marriage to lobbyist Heather Podesta. The two were a striking couple on Washington's sometimes traditional social scene, frequently photographed in front of one of their paintings or sculptures. The marriage ended after 11 years with no children but a custody battle over the art.
John, 68, declined to be interviewed for this article. Friends and colleagues describe him as more methodical, lawyerly and ideological. He's a homebody — married to his wife, Mary, for almost 40 years, with three grown children and hobbies that include cooking, running and UFOs.
But his real passion is progressive politics, and to liberals, he's a true believer and a hero.
"There's not anyone who I've worked with who is more committed, has more integrity and is just smarter — not just in politics, but how you get things done in government," says Jennifer Palmieri, who worked with him at CAP and in the White House.
Denis McDonough, who served as Obama's White House chief of staff, describes his strengths as a "fervid commitment to Democratic ideas like opportunity and justice, a willingness to fight for those ideas — and fight hard — and a practice of supporting and believing in his people, be they candidates, presidents, or fellow staff members."
Conservatives, on the other hand, consider him an unreconstructed partisan and blame him for a lot of the mistrust and anger in Washington because of the way he advised Obama to issue executive orders to circumvent Congress and the legislative process.
"There's an enormous gulf between many people's opinion of John and of Tony," said one former Republican politician. "Tony is obviously a big Democrat, but he has Republican friends and represents some clients that have more in common with the Republican side than the Democratic side. John is a hard partisan — a lot of people think of him as more strident, doing things that have never been done before to get your way."
Tony chose a smoother path and, according to lobbyists on both sides of the aisle, is respected by his peers as a creative, hands-on advocate.
Still, a successful lobbyist — and Tony built his firm into one of the top lobbying shops in the country — walks a delicate line between principle and profit. For every feel-good cause or nonprofit client, there's a corporation or a foreign government with public relations problems and buckets of money to spend.
To wit: Tony's work for Saudi Arabia has caused some raised eyebrows among human rights activists. Last year, the Podesta Group — one of several lobbying and PR shops the Saudis hired — was paid $140,000 a month by the Center for Studies and Media Affairs at the Saudi Royal Court, a government entity.
"I have no apologies to make, which doesn't mean that everything my clients have ever done is wise or admirable," Tony says. "You try to help people tell their story, and you try to make them better. I think that's all to the good."
The two brothers made Washington's "Most Powerful" lists every year. Life was good.
In February 2015, John left the White House to join Hillary Clinton's presidential campaign. It was, by all indications at the time, the start of another road to the executive mansion.
Hundreds of books will be written about the 2016 presidential race, and we'll leave it to historians to sort out the what and the why.
But one of the most unsettling chapters was Pizzagate, the debunked conspiracy theory that linked Hillary Clinton to a nonexistent child sex ring at Comet Ping Pong, a Washington pizza restaurant. The Podestas were fans, and friends with the owner, James Alefantis.
In the fall of 2016, John's personal emails were hacked and released by WikiLeaks. An enthusiastic amateur chef, he made frequent references to food, which became the basis for a theory that the emails were code for sex trafficking and child pornography. Although completely unsubstantiated, it quickly became a viral sensation and appeared on alt-right websites and forums.
The restaurant was, as Alefantis put it, "terrorized" by threatening calls and letters. "I was inundated with death threats, sometimes many a day," he wrote in an op-ed for The Washington Post. In December, after watching a YouTube video about the conspiracy, a 28-year-old man stormed in with a rifle, firing shots but not injuring anyone.
"Watching John go through the Russians stealing his emails, then working to concoct sick conspiracy theories to hurt him and Hillary Clinton was one of the toughest things to see," Palmieri says. "He acts like it doesn't bother him, but it does."
This came after another vicious conspiracy, floated just days before the election, that the Podesta brothers had secretly traveled to Portugal in 2007 and kidnapped Madeleine McCann, a British child at the center of an unsolved disappearance.
So it's no surprise that Tony Podesta's link to Mueller's indictment of former Trump campaign manager Paul Manafort has caused a frenzy.
The indictment says that Manafort recruited two firms (identified as "Company A" and "Company B") to lobby on behalf of a supposedly independent Ukrainian nonprofit. The investigation into Manafort claims that he was in fact secretly working for then-Ukrainian President Viktor Yanukovych.
Podesta and the other firm, Mercury Public Affairs, say that they were hired by the European Center for a Modern Ukraine, a nonprofit group based in Brussels, to boost Ukraine's reputation in the United States and increase its chances of joining the European Union. Both firms insist that they were unaware of any connection to the Ukrainian government. The Podesta Group received $1.1 million between 2012 and 2014 from the organization.
Its representation was originally listed under the Lobbyist Disclosure Act but not the Foreign Agents Registration Act (FARA), as required. A Podesta Group spokeswoman says that following media reports that the ECMU may have been connected to Ukraine's government, the firm submitted new disclosure forms, after which "the FARA office at DOJ informed the Podesta Group that it was not the subject nor a target of an investigation."
Legalities aside, the question among lobbyists in Washington is why someone at the top of his game like Tony would have anything to do with Manafort, whom one Republican lobbyist described as a "shady businessman advocating for murderers, thugs and thieves — even if those criminals were heads of states." Sources close to the Podesta Group assert that Manafort was not involved with the ECMU at the time the firm worked on its behalf.
Tony declined to comment on anything involving the investigation. His company has "fully cooperated" with Mueller's office and "taken every possible step to provide documentation that confirms compliance with the law," according to the spokeswoman.
But the news was enough to end Tony's tenure at his own firm. He resigned just hours after Manafort's indictment went public.
There are legendary second and third acts in Washington, long after careers have been declared dead.
So there's no telling whether there will be another chapter in the Podesta story. Will the Podesta Group survive? According to a report in Politico, chief executive Kimberley Fritts, who was widely expected to take over the helm from Tony, announced her own resignation to the staff on Thursday, throwing the company's future into question.
John, meanwhile, is closely linked with both Clinton and Obama at a time when the Democrats are desperately looking for a fresh start. But he's still considered one of the smartest strategists in politics and is likely, observers say, to advise future campaigns, although not in an official capacity.
He's going to take some time off. Travel. Relax. Refresh. And then, he insists, he'll be back, hosting parties and fundraisers and doing what Podestas always do.
"I'm not bowed. I'm not retreating," he says. "These are perilous times for the country and for the world. I hope we get through them."