Mark Penn recently moved into a brand new office on Washington, D.C.’s I Street, just a few blocks away from the White House, where he used to have an office during the Clinton administration.

It’s been a decade since Penn served as a top strategist for the Clintons, enjoying the inside-the-Beltway “genius” status conferred on architects of winning presidential campaigns. Since then, Penn has become an iconic Washington archetype: the heretic — a party insider who reliably criticizes his own team. That’s made him a villain to many of his fellow Democrats, who despise him for everything from Hillary Clinton’s flameout in 2008 to his relentless criticism of the party’s leftward lurch.


And yet the walls of Penn’s new conference room are still decorated with handwritten notes from Bill and Hillary, two poll-focused politicians who relied on his methods for 15 years and four elections between them. “Thanks for your help on this,” the president wrote to Penn on a copy of his remarks at the 2000 Democratic National Convention. “Mark — Thanks for helping me get off to a great start!” Hillary Clinton wrote on a signed copy of her Feb. 6, 2000, announcement of her Senate run.

A black-and-white photograph of Penn and Bill Clinton, huddled together behind the Resolute Desk in the Oval Office, hangs in the main conference room. In the photo, Penn tells me, Clinton is asking his advice on whether he should settle a lawsuit with Paula Jones. Penn urged him to do so, he said, but Clinton worried it would look bad.

“Had he settled,” Penn muses, “he might have avoided the whole thing.”

“The whole thing” is what Penn, who now runs the Stagwell Group, a private equity firm, has become vocal about over the past year — a special counsel’s wide-ranging investigation into a president, one that ensnares family members and senior staffers around him, exacting an emotional toll on everyone involved and damaging the president’s ability to run a functional government.

Because he was against Ken Starr, Penn’s logic is that he has a unique perspective on why Robert Mueller is harming the country, too. And as a Democrat bashing the Mueller investigation and making arguments that are useful to President Donald Trump, Penn has found a prominent new perch in the Washington ecosystem. Our interview was the first time he’s explained his Trumpian turn, which has earned him fresh enmity on the left.

Penn has now become a regular face on Fox News — CNN and MSNBC won’t book him — and a contributor to The Hill’s right-leaning editorial pages. There, he has repeatedly bashed the Mueller investigation as a “partisan, open-ended inquisition that, by its precedent, is a threat to all those who ever want to participate in a national campaign or an administration again” — followed up by more TV hits on Fox.

And despite the photos that decorate his office walls, he has willingly torched the Clintons, saying the Justice Department “broke their own rules” by ending an investigation into Hillary Clinton’s use of a private email server, and noting that “Clinton Foundation operatives” urged the FBI to investigate Trump.

Penn makes no distinction between Trump’s frequent fulminations against the Mueller investigation — which has raised questions about whether the president is obstructing justice — and the Clintons’ handling of the Starr probe. “The Clintons didn’t put their emotions on Twitter, but trust me, they had them, and they weren’t particularly different from Trump’s,” he says.

Mark Penn, then chief strategist and pollster for then-Democratic presidential candidate Hillary Clinton, speaks to reporters in the 'spin room' after the Democratic debate at Saint Anselm College January 5, 2008 in Manchester, New Hampshire. | Win McNamee/Getty Images

Bill Clinton has swatted away Penn’s commentary as sour grapes. “He wasn’t invited back into the campaign,” Bill Clinton said in a recent “PBS NewsHour” interview. “He’s been mad about it, and I think it’s silly.” He called Penn’s arguments “silly and dangerous.”

“He knows better,” the former president said.

Other Clinton loyalists view Penn as a mercenary and a traitor. “I go on Fox to show the blue flag,” says Philippe Reines, who served as Hillary Clinton’s longtime gatekeeper in the Senate and at the State Department. “When Mark goes on, he might as well be waving a white flag.”

Reines, who allows that Penn shouldered too much of the blame for Clinton’s 2008 defeat, adds: “I think he wants relevance and I think he wants revenge.”

If that’s what’s driving him, he’s certainly succeeding. After a decade in the political wilderness, left behind by his own party, Penn is finally being talked about again.

Penn doesn’t quite see it that way. “I just find it funny that Philippe carps about [me] appearing on Fox News when he appears on Fox News,” he said in an email. “I’ve been a principled moderate for over 40 years, regardless of where I appear, and that at times has driven both the right and the left crazy.”

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Penn, 64, is a member of a small club of Democrats in Washington shaped by Whitewater and the independent counsel investigation it spawned — people who learned firsthand what it was like to deal with a special force of nature: a wide-ranging probe that ripped through the government in the prime of their professional lives.

Penn says this is the snow-white motive that drives him: scar tissue that has given him a unique perspective on special prosecutors. As he thinks of himself: I’ve seen this movie before, when the roles were reversed, and I’m willing to be the rare nonpartisan who is consistent in my views about overreaching investigations.

“Maybe I’ll have egg on my face,” he says of Mueller’s Russia probe. “But if I’m looking at the scoreboard, I’d say he had some show indictments, [Trump has] never had any real connection here to any Russia collusion conspiracy as was advertised, the dossier was a sham document from the beginning, what the FBI and the Justice Department did was fundamentally biased. If this whole thing devolves into Cohen, it will prove the destructiveness of these investigations just as it did in 1998.”

Sitting in his conference room, across from the Oval Office photo with Clinton, Penn recalls one moment when he realized how destructive it all was. “I got a phone call at 1 a.m., and it’s the president, and he’s explaining to me there’s this really bad guy, Osama bin Laden, and he can hit him with some missiles,” he says. “But he was worried that maybe that would be interpreted as wagging the dog.” Penn advised Clinton not to worry about the optics, and the president ordered the missile strike, which ultimately failed to take out bin Laden. But Penn says the fact that the investigation even factored into his thinking was the problem. “It illustrated to me that anybody under the circumstances who is president of the United States, who is also facing an investigation, has to think differently about how they manage the presidency.”

Watching Trump rage against Mueller’s “witch hunt” and rail against his own attorney general, Jeff Sessions, Penn says he’s having déjà vu all over again.

“I don’t know if they used the word ‘witch hunt,’” he says of the Clintons now, “but let’s just say they would have not had the greatest regard for Janet Reno, either. There was a lot more emotion than you ever would have realized about that.” (A Clinton spokesman noted that the former president eulogized Reno at her funeral in 2016.)

If he’s able to see parallels between then and now, he says his former bosses do not. “The Clintons believe there was a Russian conspiracy that stole the election,” he says. “They believe that.”

And where most Democrats believe Mueller is sticking to his mandate of investigating Russian interference in the 2016 election, Penn is convinced he is overreaching. “It’s devolved into 1998,” he argues. “I haven’t been persuaded by the evidence that’s come out so far that the Russia collusion theory was little more than a theory. And on the basis of that theory, they’re able to investigate the entirety of the campaign, and the administration. It would drive anyone relatively over the edge.”

But Penn may be alone in his view of himself as a maverick willing to speak truth to power even if it’s unpopular with his own party. In interviews with his former colleagues, most said they see a much more common human story at play: a man who lost his home in his own party, both ideologically and personally, someone who hasn’t been consulted by Democratic presidential candidates in years, who is suddenly finding political relevance again by spouting — whether he intends them to be or not — what amount to pro-Trump talking points.

Most of that newfound relevance is coming from the right. The Republican National Committee spokeswoman Kayleigh McEnany recently tweeted a Penn column, calling it a “MUST READ.” Former Arkansas Gov. Mike Huckabee linked to a Penn column in which he called former Trump attorney Michael Cohen’s plea deal an attempt to “set up” the president, writing, “I defer to Mark Penn.”

White House aides often rely on Harris polls — a company Penn acquired last year — to show the president how he’s doing with blue collar voters, and an aide said Trump was aware of Penn's commentary, mostly from seeing him on TV.

If this bothers Penn, he doesn’t let on. In our interview, he even implied that he may have a new admirer in the Oval Office, possibly due to regular appearances on shows the president watches regularly, like “Fox & Friends” and “Mornings With Maria,” featuring the Trump-friendly Fox Business anchor Maria Bartiromo. “I don’t comment on whether I talk to people or not,” he says. “I don’t have any relationship with Trump. I never met the guy, but I’m not going to comment on whether anyone reaches out or not.” (A White House spokeswoman did not respond to requests for comment about whether Trump had ever reached out to Penn.)

Penn rejects a comparison to Dick Morris, another former Clinton consigliere who later became a sharp critic of the former president and a frequent guest on Fox News. “I haven’t flipped at all,” he says. “I’m not in politics. If my goal was to please people in politics, it would have been easy as pie to go out there and get some talking points every day about why we should be impeaching the president. Those aren’t my values, and they aren’t how I got my job with the Clintons in the first place.”

He’s more comfortable with a comparison to Alan Dershowitz, the Democratic law professor who has become a favorite of Trump’s and a pariah on Martha’s Vineyard because of what people interpret as his vociferous defenses of the president.

Dershowitz, however, doesn’t like that comparison. “Mark Penn is more involved in political assessments than I am, and his politics are slightly more conservative than mine are,” Dershowitz said in an interview. “I draw a sharp distinction between us. I would never use the term ‘Deep State.’ I attribute good faith to the Mueller investigation.” (Penn wrote a column last month titled, “The Dishonesty of the Deep State.”)



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Outside of politics, Penn appears to be thriving, even if some of the people who technically work for him would prefer he stay quiet on the Trump front. His desk is fashioned out of a former airplane wing, symbolizing that his firm is “taking off,” he says. He recently completed a $260 million fundraising round. His portfolio of 17 companies he owns includes one of the most influential Democratic firms in Washington, SKDKnickerbocker, and a Republican firm, Targeted Victory, founded by alums of Mitt Romney’s 2012 campaign.

To people who work at those companies, Penn is known as a completely hands-off manager when it comes to the political shops, and more involved day-to-day with his tech companies.

It’s been a remarkable journey for a once-obscure New York pollster who was catapulted into the national political limelight after providing polling and analysis to Bill Clinton during his 1996 reelection campaign. He then took over the prime position of trusted strategist after Morris was ousted because of a relationship with a prostitute (toe-sucking was involved). Back then, Penn was desperately devoted to the Clintons — to the point that Vice President Al Gore worried his loyalty to them would make him a liability on his own 2000 presidential campaign and didn’t offer him a job.

Penn worked on Hillary Clinton’s 2000 Senate race instead and was responsible for pushing her into a strategy that focused on upstate, typically a no-go zone for Democratic candidates. After leaving politics, he entered the world of corporate consulting as the chief executive of Burson-Marsteller, a global public relations firm. There, he pitched what CEOs crave most: the promise of the best practices of campaign war rooms brought into the corporate boardroom.

Hillary Clinton’s 2008 campaign offered Penn what people in his business refer to as a “political refresh,” i.e., lasting relevance in both the business and political realms. But after he was widely blamed for that loss — and reviled by Obama world as well as Clinton veterans — he found himself persona non grata on the left after her defeat. He took particular grief for a 2007 strategy memo that called for highlighting Barack Obama’s “lack of American roots.”

“It’s hard being in a city where your own party shuns you,” observes Reines, who recalls that Penn was so reviled that he became a problem in retiring Clinton’s campaign debt after the 2008 defeat. “They had to pay back Mark last because people would not donate to pay off Mark,” Reines says. “They would make a point of telling people his debt would be last.”

Penn acknowledges that the party has moved in a different direction. “They were livid when I said we should go after soccer moms,” he says. “They were livid when I said we should go to the center. They were livid with me from the beginning. My views haven’t changed at all. The party’s changed.”

He says he still firmly believes that “Democratic voters are not radical Democratic socialist voters. They are by and large centrist voters.” That view doesn’t have much currency in a world where progressive icons Bernie Sanders and Alexandria Ocasio-Cortez have generated the most enthusiasm in recent elections.

But Penn’s new position has given him that political “refresh” and relevance, even if it’s with a different audience. The man who was known as the architect of the “new Democrats” has redefined himself as something that looks fairly pro-Trump.

“He didn’t have a single day in office without being under investigation,” Penn says of the current president. “That’s an incredible weight on anyone trying to form a team, run a government, make decisions.”

He says people make a mistake in underestimating Trump. “He didn’t have a show on TV. He had the No. 1 show on TV,” Penn says. “He won an overwhelming victory.”

Penn says he still considers himself a Democrat who would never vote for Trump. But all of that is secondary. “I care about the process more than the outcome,” he insists. “I believe that if we keep our process as pure as we can, in the end voters will win out and they will make intelligent decisions. We have elections every two years. By putting the country through this process and throwing him out in advance of his period, you are not accomplishing anything.”

And if Trump wins reelection in 2020? “Then you better wake up to the country you live in.”