When Stormy Daniels appeared at Donald Trump’s penthouse hotel room, on the lustful summer night in 2006 that has come to haunt his presidency, the two were not entirely alone.
Trump’s loyal bodyguard—a towering former NYPD detective with clipped white hair and a steely expression—met her at the door to the suite, according to Daniels’ account of the alleged tryst. Keith Schiller had already worked for his reality-TV star boss for seven years, ever since a chance encounter with Marla Maples in New York, and he’d quickly risen through the ranks to become Trump’s head of security. Now, he and his boss were in Lake Tahoe for a celebrity golf tournament and, as several women present for the bacchanalian weekend would attest, Trump was looking to get laid.
Schiller was apparently ready to help.
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Earlier that day, Trump—newly married for a third time, with an infant son at home—had visited the curvaceous, blond Daniels at a promo booth for Wicked Pictures, the adult-entertainment studio where Stormy was a “contract girl.” (They’d already shared a flirty ride around the course in a golf cart, Daniels claims.) While there, Trump also ogled another blond bombshell, porn star Jessica Drake. As the women tell it, he scored both of their phone numbers. He singled out Daniels in particular for a dinner date.
As night fell, Daniels arrived at Harrah’s Lake Tahoe Hotel and Casino, where Trump was staying. Eighteen floors up, and she found herself face-to-face with the hulking Schiller.
“Keith was always with him,” the porn star told In Touch Weekly in 2011, five years after her alleged romp with the future president. “That’s how I got in touch with him. I never had Donald’s cellphone number. I always used Keith’s.”
For a man so notoriously loquacious on Twitter, Trump has kept an ironclad grip on the particulars of his personal life.
He’s master of the NDA for his Trump Organization employees and former campaign staffers, even trying to ensure White House staff can’t talk. And throughout the years, he’s relied on a small cadre of fixers to help muzzle those who dared blab about his private peccadilloes. One of those loyalists is Michael Cohen, Trump’s personal lawyer who was the target of a federal raid, reportedly over his role in paying Stormy Daniels to keep quiet, and possibly for his communications with The National Enquirer, whose owner David Pecker is a strong Trump ally.
The magazine’s parent company bought the silence of at least two people with stories that would have been spectacularly damaging to Trump just before the election: Playmate Karen McDougal, who claims she and Trump had a long affair during the same time he was wooing Stormy Daniels; and a Trump World Tower doorman who apparently had intel on rumors about a secret Trump love child.
The other main fixture of Trump’s inner circle—one of the few who seems to know all the details about all the women and, like Cohen, is a person of interest to the investigators of the Russia inquiry—is Keith Schiller.
Schiller did not return messages left by The Daily Beast, and one of his attorneys declined to comment for this story.
“There is no doubt that Keith Schiller knows where all the bodies are buried. Next to Michael Cohen, if Mr. Schiller ever turns state’s evidence, the impact on the president would be catastrophic,” Michael Avenatti, the lawyer for Stormy Daniels, told The Daily Beast.
While the national focus has been on Cohen, Avenatti says Schiller is a Trump stalwart who’s long been on his radar.
“He’s knee-deep in all of this,” Avenatti said.
Perhaps no one in Trump’s inner circle, save for Michael Cohen, has the president’s trust more than Schiller. But where Cohen is brash and fiery, Schiller has remained a low-key presence in his boss’ shadow.
Politico has called Schiller “Trump’s longest-serving and closest aide—the man who is widely credited with knowing how to manage the president’s moods, his diet, what triggers him and what soothes him.”
“There are only two whisperers in Trump world, as far as I’m concerned,” one former aide told Politico last November, adding, “it’s Keith Schiller and Michael Cohen.”
As Trump’s hired muscle since 1999, Schiller has allegedly facilitated Trump’s extramarital excursions, socked a protester outside Trump Tower, and delivered former FBI Director James Comey’s termination letter.
Schiller skyrocketed from part-time watchman to Trump’s director of security in just under six years. And he followed his boss to Washington as head of Oval Office operations, where he served as gatekeeper, confidant, and fixer for Trump’s McDonald’s cravings. He was an interpreter, too, for frustrated aides.
The 59-year-old former detective has been described as Trump’s “loyal lieutenant” and “emotional safety blanket.” Trump reportedly was “crushed” when Schiller departed the White House last September for a private security gig. Even Cohen was worried about how Trump would react in the wake of Schiller’s exit, telling Vanity Fair, “I feel guilty that he’s in there right now almost alone, especially now that Keith has resigned.”
As Schiller has maintained a low profile, Cohen catapulted to the white-hot center of the news after Stormy Daniels filed a lawsuit against him and Trump, to invalidate a “hush agreement” she signed in the weeks leading up to the 2016 election. She says the contract is invalid because Trump never signed on the dotted line—and because it violated public policy by suppressing her speech in order to influence the race.
Cohen is now facing more legal troubles after the FBI raided his office last week for documents relating to, among other things, his $130,000 payout to Daniels in exchange for her silence about the alleged Trump affair.
Trump railed against the search as a “witch hunt,” and floated the possibility of firing Rod Rosenstein, who oversees special counsel Robert Mueller, after the latter referred the Cohen probe to the U.S. Attorney’s Office for the Southern District of New York.
Vanity Fair highlighted Trumpland’s fears of the “brooding” president going rogue and also firing Mueller. Trump was usually calmed by former aides Hope Hicks and Schiller, whose departures have left “Trump to operate largely unchecked.”
Last year, ex-campaign manager Corey Lewandowski told CNN he’d regularly call Schiller anytime he needed help deciphering The Donald.
“Any time I wanted to understand something, I would ask Keith,” Lewandowski said. “I valued him for all the roles he played.”
One of those roles, apparently, was acting as liaison to women who caught Trump’s interest.
Back to the Tahoe penthouse. July 2006. Stormy Daniels is on the verge of an encounter that will, a decade later, turn her into a household name and attract an astounding 22 million viewers when she spills the dirty details—the spanking, the unprotected sex—on the venerable news program 60 Minutes. And, she says, the person greeting her at the door is Trump’s buzzcutted consigliere Keith Schiller.
“Oh yeah, he’s waiting for you inside,” Schiller allegedly told Daniels, before she entered the room and found Trump lounging in pajama pants.
After they were intimate, the porn actress says Trump promised, “I’m gonna call you.”
“I have to see you again. You’re amazing,” he added.
Later that same night, porn star Jessica Drake remembers Trump inviting her, too, up to the Harrah’s penthouse. She was uncomfortable going alone, Drake claimed at a press conference with her attorney Gloria Allred, so she took two other women along. (Those gal pals haven’t yet been identified.)
“When we entered the room, [Trump] grabbed each of us tightly in a hug and kissed each one of us without asking permission,” Drake told reporters in October 2016.
“He was wearing pajamas,” she continued. “A bodyguard was also present.”
The group left after about an hour of idle chit-chat. But when Drake returned to her hotel room, a man called her on Trump’s behalf, according to an account in GQ of Trump’s Tahoe trysts. The man asked Drake if she’d return to Trump’s suite. She declined. Soon, she says, Trump phoned her directly and asked her, “What do you want?” and “How much?” On a third call, he allegedly wooed her with an offer of $10,000 and use of his private jet in exchange for sex. She again declined.
Drake has not publicly disclosed whether Schiller was the bodyguard at the penthouse, or whether he was the man who contacted her on Trump’s behalf. Neither Drake nor Allred returned messages seeking comment.
Yet the next evening, Stormy Daniels got a similar call—from Schiller for sure, she says—asking if she’d join Trump and his fellow celebrity golfers. When she arrived, Schiller was the one to escort her to Trump, who was schmoozing with NFL star Ben Roethlisberger.
Months later, Schiller would again greet Daniels at a Hollywood launch party for Trump Vodka and steer her to Trump’s VIP section.
And in July 2007, the wingman was tasked with ushering Daniels to Trump’s bungalow at the Beverly Hills Hotel. Daniels says Trump blustered about his hatred for sharks before confessing that his efforts to get her on The Apprentice had failed. Then he propositioned her, asking, “So, can you stay?” But she’d lost interest in the mogul; she dismissed Trump’s advances and left. Their meeting lasted for two-and-a-half hours. At the end of it, she says, Keith Schiller politely walked her to her car.
Former Playboy model Karen McDougal also mentioned Schiller by name last month in her CNN interview with Anderson Cooper, in which she dished about her alleged affair with Trump. The onetime Playmate of the Year met the reality star in June 2006—just a month before the Tahoe bash—at a party at the Playboy Mansion, where Trump was taping an episode of The Apprentice. Not long after, on a summer night in L.A., she said, Schiller picked McDougal up and drove her to the Beverly Hills Hotel bungalow, where she met Trump for dinner.
McDougal said she had unprotected intercourse with Trump that night—“We talked for a couple hours – then, it was “ON”! We got naked + had sex,” she later jotted in her notes, according to The New Yorker—and was heartbroken when he tried paying her afterward. “I’m not ‘that girl,’” she told him. She wept in the car as Schiller drove her home.
As her affair with Trump persisted, McDougal said she “got to know Keith pretty well.” The 6-foot-4 protector “was always involved” in her communications and visits with the future president. McDougal kept Schiller’s phone number and the digits for Trump’s personal secretary. Both would put her in touch with the real estate mogul.
“Keith is a nice man,” McDougal told Cooper. “Yes, I got to know him. He’s funny.”
A year later—on a winter eve this time—another woman met Trump at that same Los Angeles bungalow. Their encounter would turn out to be more fraught than the president’s other romps.
As with McDougal and Daniels, Trump enlisted his “security guard” to bring Apprentice contestant Summer Zervos to the Beverly Hills Hotel. Zervos’ lawsuit doesn’t identify the man by name, and her attorney did not return messages seeking comment on the identity of the bodyguard.
When Zervos arrived, she says her TV boss ambushed her. He kissed her “very aggressively” and touched her breast, according to a pending lawsuit. She repeatedly pushed the mogul away, and moved to another part of the room to avoid his advances until he finally relented and ordered dinner—a club sandwich and fries. He reportedly complained about the price.
Zervos is now suing Trump for defamation, and says the Beverly Hills encounter was one of several in which Trump kissed her, groped her, and pressed himself against her without her consent. In the run-up to the 2016 election, Zervos came forward as one of more than a dozen women to accuse Trump of sexual misconduct.
Trump has adamantly denied all the women’s claims—and those of Daniels and McDougal—both on Twitter and through statements from the White House. After three accusers went on Megyn Kelly Today in December to discuss their experiences with Trump in light of the #MeToo movement, a spokesperson for the president said, “The timing and absurdity of these claims speaks volumes and the publicity tour only confirms the motives behind them.”
Meanwhile, this past November, the House intelligence committee grilled Keith Schiller about another group of women rumored to be linked to Trump. This time, though, the setting was not at the shady greens of Lake Tahoe nor in the glittering heart of Beverly Hills, but in Vladimir Putin’s Russia.
It was November 2013, and Trump was in Moscow for the Miss Universe pageant. During a meeting at the Ritz-Carlton, where Trump was staying, a Russian participant approached Schiller and offered to send five escorts to Trump’s hotel room, the bodyguard testified. He said he dismissed the proposal as a joke and told the stranger, “We don’t do that type of stuff.”
Schiller’s comments were in reference to the so-called Steele dossier, penned by a former British spy, which alleged that Trump had engaged in “perverted sexual acts” with Russian prostitutes and that the Kremlin had tapes of the sexcapades as potential blackmail fodder. Trump and his team have called the Steele dossier’s claims “fake news” and “a total political witch hunt.” Cohen, who is suing several parties involved with the publication of the dossier, called the report “ridiculous on so many levels.”
Schiller’s closed-door testimony about the Russian prostitutes—those beauties supposedly at the center of the infamous “pee tape”—came before a House panel investigating Russia’s meddling in the 2016 presidential election, NBC News reported.
In a contradictory bit of news this week, former FBI Director James Comey claims in his new book that Trump told him he did not spend the night at the Ritz-Carlton, and therefore the pee tape couldn’t be true.
But Schiller said he informed Trump of the Russian prostitute proposition as they returned to his hotel room that night. They both laughed at the idea, and Schiller guarded Trump’s door for a bit before heading to his own quarters.
Trump went to bed alone, he said.
As aide-de-camp, Schiller has learned to anticipate his boss’ wishes.
In August 2015, Schiller removed Univision journalist Jorge Ramos from an Iowa press conference. Trump refused to take a question from Ramos, who also wouldn’t back down, prompting Schiller to stride menacingly across the stage and push Ramos out of the room.
When asked about the confrontation during a deposition, Schiller said, “I took it upon myself to go and remove him, because it appeared that he was dominating the news conference, not listening or not being cordial or respectful to Mr. Trump…”
The deposition was for a lawsuit filed by Efrain Galicia and four other Mexican activists, who claim Trump’s security guards attacked them during a September 2015 protest outside Trump Tower. Schiller had asked the demonstrators to remove an 8-foot-long “Make America Racist Again” poster. When they refused, Schiller ripped the sign away and headed back toward the building, the complaint says.
Galicia followed Schiller, whose back was facing him. When Galicia attempted to retrieve the sign, Schiller swung around and clocked him. (Schiller says he believed Galicia was reaching for his concealed weapon, a deposition transcript shows. He said he used a “minimal amount of force to get [Galicia] off of my firearm and off of my body.”)
During the December 2016 testimony, Schiller claimed he’d never discussed the Galicia incident with Trump. Schiller said Trump never asked about the encounter, despite being named as a defendant in Galicia’s pending suit.
When asked if he always obeyed Trump’s orders to remove disruptive people from events, Schiller replied, “Not always, no.” If someone complied with requests to be quiet, Schiller said he would let them stay.
“I’m not a robot,” Schiller said. “It’s been times when it wasn’t appropriate and I didn’t do it.”
Schiller has shied away from media interviews. But he did grant a one-hour videotaped conversation to his childhood friend, author Rich Siegel.
“I spent a lot of time at bars with him,” Siegel said. “If he thought something was wrong, he was ready to get his fists in there... There was never a fight he strayed away from.”
Siegel and Schiller grew up together in New Paltz, New York, before Schiller joined the Navy. He married his wife, Lena, when he returned home.
In 1992, he began his NYPD career as a transit cop near Yankee Stadium. In the interview with Siegel, he said he became a narcotics investigator and did cocaine busts in the Washington Heights neighborhood of Manhattan.
Schiller routinely took cases to the Manhattan district attorney’s office. During one visit, he spotted Trump’s second wife, Marla Maples, with her personal bodyguard. “I looked at him. Totally not impressed by his stature, physical stature,” Schiller told Siegel in the 2016 video. “I said, if he’s a bodyguard, I sure as f*** is a bodyguard.
“I’m no stranger to putting my hands on people,” he added.
“I ask the ADA, ‘Do you know Donald Trump?’ He says, ‘Yeah.’ I says, ‘Can you put in a good word? I’m looking for side work,’” Schiller said.
Trump’s security boss gave Schiller a one-month trial that blossomed into a 19-year constant companionship. “Every night we were out with different events. Fashion shows. Baseball games. Whatever,” Schiller said.
“In the beginning it’s a fascinating job,” he said, adding, “Believe me, so from where I came from, it’s an eye-opener and a great experience.”
In 2004, Trump transferred his then-head of security to Las Vegas and needed one of a handful of part-timers to rise in the ranks.
“He said, ‘The only guy that I feel that can do this is Keith,’” Schiller said. “I had a great rapport with Mr. Trump and I still enjoy that.”
