Last August, Roger Stone had a serious falling-out with his longtime friend and boss Donald Trump over campaign strategy.

He thought Trump ought to have one.


Stone, Trump’s most influential and seasoned political adviser at the time, says he quit after the do-it-myself billionaire rejected his plans to create a traditional campaign structure and a suggestion that he seek to broaden his pitch beyond working-class whites. Instead, Trump put his mouth where he wouldn’t put his money, opting for an on-the-cheap one-man road show, fortified by monster debate ratings and an unavoidable-for-comment approach to cable and network TV interviews.

“You don’t manage Donald … you can't deal with him on that basis,” Stone, nursing a mild martini hangover the morning after celebrating Trump’s blowout win in the New York primary last week, explained. During an hourlong sit-down for POLITICO’s “Off Message” podcast, the 63-year-old former Dick Nixon dirty trickster offered a candid assessment of his longtime boss’s strengths, blind spots and daunting path to the presidency.

“He envisioned a campaign which was all communications,” said Stone — who has bounced back in recent weeks to re-emerge as a key adviser to Trump as the tycoon faces a dangerous new phase of his storybook 2016. “But the notion that you could combat — let’s take Florida — $40 million worth of negative television simply by going on ‘Fox & Friends’ and responding, I rejected that idea.”

Stone doesn’t have a formal relationship with the campaign (his role is limited by his stewardship of a pro-Trump super PAC) and he wouldn’t tell me how often he talks with Trump or his top aides. But the campaign’s shotgun reorganization (his former lobbying partner Paul Manafort has layered over Stone’s rival, campaign manager Corey Lewandowski) — and germinating kinder-gentler general election pivot — bears Stone’s fingerprints.

“He’s going to have to better articulate himself on issues that are of concern to women,” Stone said of Trump, stating an obvious truth that, until recently, wasn’t all that obvious to a candidate who prides himself on political incorrectness. “He is going to have to define a pro-growth, more aspirational message for African-American voters, for Hispanic voters, where I actually think he can make inroads.”

When I asked Stone how Trump could possibly do that — and whom he should tap as a running mate— he threw out John Kasich’s name almost by rote. Then he settled on a choice that seemed to better capture his imagination: “Little Marco” Rubio.

(Subscribe to POLITICO's Off Message podcast with Glenn Thrush)

Stone, who worked as a dark-arts political type for Nixon and later Ronald Reagan, is a paradox in wide pinstripes and oval 1930s movie-star shades. He’s known for scorched-earth muckraking (he co-authored a book dredging up Clinton scandals and recently emailed me to say that the Clintons should “be worried” about him because “I know exactly how to take them down”) but he desperately wants Trump to make his peace with women and minority voters. Stone’s the ultimate Donald insider (he’s been on Trump’s payroll, on and off, for 40 years) but his habit of telling Trump what he thinks has created an arm’s-length distance. He’s infamous for his profane tirades and crass Twitter outbursts (he once mocked Al Sharpton — a onetime friend — with a fried-chicken joke) but he’s a charming conversationalist who speaks authoritatively about political biographies and pines for lazy Saturdays lost in the stacks of Manhattan’s famous Strand bookstore.

Even his trademark — a big Nixon tattoo planted between his shoulder blades — sends a mixed, nuanced message. It’s not actually an expression of affection for his one-time boss (he likes Reagan and Ike a lot more, idolizes his libertarian hero Barry Goldwater and modeled his brass-knuckle approach to politics on Bobby Kennedy’s wet work); it’s an homage to Nixon’s “resilience,” and he had it etched on his back at a time when he was suffering from a debilitating ailment that left him bed-ridden, deeply depressed and in need of an emotional boost.

Still, warm and fuzzy isn’t Stone’s thing; maybe that’s why Trump ushered him back into the fold. Ted Cruz personally called out Stone for purportedly leaking a salacious story to The National Enquirer about the Texas senator’s alleged extramarital affairs; Stone has repeatedly denied he did it (to me and others), but he loves that Cruz thinks he did it. “I think I'm in Ted Cruz’s head right now. He’s got his paid shills, Glenn Beck and Mark Levin, attacking me viciously,” Stone said. “I have to assume that Ted Cruz is laying awake at night worrying about what I'm doing next.”

He hopes to play the same trick on Hillary and Bill Clinton. “Part of the strategy of any campaign is to psych out the opposition,” he added. “There's no question that Karl Rove got into John Kerry's head. ... I think they're more vulnerable than most because they have more crimes to hide.”

Stone, one friend told me, was stung by Trump’s rejection of his advice – and hurt even more by the developer tweeting that he’d fired Stone. But history has vindicated the son of a Connecticut well-digger and a Sicilian-American mother whom he compared to Livia, Tony Soprano’s merciless, Machiavellian mother in HBO’s “The Sopranos.”

Trump’s early no-plan plan — overseen by a surly, obscure GOP operative named Corey Lewandowski — worked brilliantly, Stone told me, at least for a while. That was, until Trump’s lack of state-level organizations led to defeats in Wisconsin and, in the delegate game, Louisiana — and Trump’s Jackson Pollock splattering of invective resulted in national disapproval ratings that pushed an unheard-of 70 percent.

Stone believes the recent shake-up is a vital first step toward victory against Clinton, whom he sees as a weak and vulnerable foe. Lewandowski, Stone told me with a sly smile, wasn’t really a full-service campaign director, but a “tour director” with a narrow, logistics-minded approach that reminded him of his former colleague in the Nixon White House, John Ehrlichman, who served jail time for the Watergate cover-up.

You want to set up a well-executed rally and create a database of all the attendees? Stone asked. Lewandowski is your guy. “He was the right campaign manager for that model because the model consisted of a well-run tour. … Now, you're just in a different phase of the campaign.” he added.

“Actually, he reminds me more of [domineering Nixon chief of staff] Bob Haldeman, but maybe that's just the brush cut.”

Stone’s core disagreement was never with Lewandowski, but with another supremely self-confident novice: Trump, his employer and friend since the late 1970s. Like nearly everyone in Trump’s orbit, Stone is exceedingly reluctant to publicly criticize the boss (possibly because of the nondisclosure form he signed) and he thinks Trump’s “amazing” political instincts have been enough to get him this far. But he believes Trump could still have executed his part of the campaign — the speeches, the debates, the media — while letting professionals (like Stone and Manafort) master the details Cruz’s campaign has exploited in victories that have denied Trump an easy path to the nomination.

“Without telling tales out of school, because I have a nondisclosure, ... I envisioned a campaign that used the more traditional tools of polling and analytics and targeting and paid media, and a greater depth of organization,” said Stone.

But organization isn’t what Trump is about, and Stone offered tantalizing behind-the-scenes glimpses of a gifted self-taught politician still learning a new trade, a creature of habit who “doesn’t surf the Web” ever, and still gets much of his news from tabloids. The presidency is a drinking-data-through-a-firehose job, but Trump, Stone told me, is reluctant to even sip the water fountain; he finds even minimalist policy briefings to be eye-glazing, Jeb Bush-level bores. Stone loves Trump — he says he’s one of the funniest people he knows — but conceded it’s “an adventure” trying to counsel a reality-TV billionaire who refuses to be scripted or stage-managed.

Stone paused when I asked him how he — or any other adviser — could change the developer’s mind once Trump had been set on a course of action. Tread lightly and keep it punchy was his best advice.

“When you know somebody that long, you get an understanding about how to affect their thinking without being, you know, without being insulting or overstepping a line,” he said. “Nobody puts words in Donald’s mouth. He is his own conceptualizer. All you can do is present information and let him either assimilate it or not. When you write something for him, keep it short and staccato. He’s not going to read a 40-page white paper on the economy; zero chance of that. ... Reagan was a big-picture guy. Trump is a big-picture guy.”

Stone is sanguine about Trump’s chances, despite predictions by the likes of Larry Sabato and Nate Silver that he will suffer a historic Electoral College blowout.

“I think that obviously he has some challenges going into the general election. But I think they’re all soluble,” Stone said.

That doesn’t mean he’s not worried, like most GOP elders, about the effect the looming convention in Cleveland will have on Trump’s candidacy, despite his own public bravado on the topic. Even as he was savoring the big New York win, Stone fretted that Trump’s continued insistence on whipping up his supporters to confront protesters at his rallies would ultimately backfire and possibly spark riots that would hobble his general election campaign before it begins.

“I would suggest that [we] just don’t step into that trap,” Stone said. “This is going to be the biggest challenge in Cleveland ... I lived through the ’68 campaign. I worked for Nixon. I saw what the violence in Chicago did to Hubert Humphrey’s prospects. Any violence in Cleveland would be counterproductive to Trump’s general election prospects.”

This from a man who had recently suggested, in watch-out-or-you-might-get-hit-by-that-dump-truck fashion, that Trump’s army of supporters might want to hunt down any pledged delegates who were thinking of defecting to Cruz if the convention fight came to a second ballot. (Stone says his comment was taken out of context. “In no place did I advocate going and physically beating on delegates.”)

Stone, after all, has been living on the shady outskirts of political respectability from his earliest days in politics: As a 19-year-old college student working on Nixon’s 1972 campaign he was tasked with framing a rival politician by making a fake contribution to the Socialist Party with a pickle jar full of dimes and quarters. His love of skullduggery also reflects a love of the theatrical — another bond with Trump — that was fostered even earlier: As a kid he grew up idolizing movie stars (“I wanted to be Gary Cooper,” he told me, an interesting idol for a guy who likes to wear the political black hat).

His politics are mostly in step with Trump’s, but he skews a lot more libertarian. Stone is fiscally conservative and has bonded with the boss on his opposition to the Iraq war, but unlike Trump he’s a backer of gay marriage and abortion rights.

When I asked him whether Trump’s flip-flop on choice was politically expedient, he shakes his head and offers a personal observation. “I do think that the birth of his youngest child really profoundly changed his views on abortion,” he told me. “You go back and you look someplace where he was talking about this, he said, ‘You know, I had a friend, and this friend and his wife had a baby late in his life,’ and then it occurred to me, he's talking about himself, but it’s a little too personal, I think, because he and his wife had [their 10-year-old son] Barron when Donald was in his 60s.”

Many Trump surrogates refuse to even acknowledge the possibility that the great man could lose — much less suffer a landslide to Clinton — but Stone knows how tough the race will be. Still, he argues two factors will deliver his guy to the Oval Office: so far secret dirt he plans to dump on the Clintons, and Trump’s innate capacity to project strength through mass media.

Stone’s relationship with Trump seems to be grounded in real admiration, and he confesses to have been star-struck from their first meeting. “You know, he seems greater than any mortal human,” he told me.

“I've often thought that his celebrity status was the greatest asset he brought to this, enhanced enormously by 15 seasons of ‘The Apprentice,’” Stone added. “I understand that elites look at that and say, ‘Oh, it's reality TV.’ But to voters, there’s no line between the news and reality TV. It's all TV. It’s all television. If you see Trump in ‘The Apprentice,’ he’s in the high-backed chair. He’s perfectly lit. He’s perfectly made up. He’s perfectly coiffed. He’s perfectly dressed. And he’s decisive. He’s tough. He’s making decisions.

“He looks and acts like what you think a president should be.”

