Who is Rudy Giuliani’s friend ‘Charles’? An accidental text may have outed his identity

At the end of September, a journalist friend gave me Rudy Giuliani’s phone number. When I called, he picked up on the second ring and promptly divulged previously unreported details about his collaboration with State Department officials on a quid pro quo this summer. Those conversations helped inform a report I filed with BuzzFeed, which was corroborated the next day in testimony and text messages from former Special Envoy to Ukraine Kurt Volker.

Giuliani forgot my name almost immediately, but we kept in touch. Truth is, I enjoy speaking with him. Two days after publication, on the evening he attended a Yankees playoff game with Alan Dershowitz, Giuliani — President Donald Trump’s 75-year-old informal cybersecurity adviser — accidentally texted me what appeared to be a password: Eight characters, beginning with the name of a networking company and including a capital letter, a special character, and a number. Multiple IT experts confirmed it could be nothing else, and, given the iPhone’s messaging setup, impossible to type with your butt or in any other unwitting way.

After an internal ethical debate, I alerted him. He replied, “Oh, that was just a butt dial,” but thanked me, punctuated with a smiley-face emoji.

Giuliani runs a global cybersecurity firm, but his technological gaffes have become legendary. After texting me the password, an NBC report revealed that around the same time he’d butt-dialed a journalist and accidentally left a voicemail documenting his discussion with an associate about how to get cash. “You know,” Giuliani says at the beginning of the recording, “Charles would have a hard time with a fraud case ’cause he didn't do any due diligence.”

At the time it was unclear who “Charles” was, but I might have found him. And I found him, through all things, in Giuliani’s attempt to straighten up his media act.

After an internal ethical debate, I alerted him. He replied, “Oh, that was just a butt dial,” but thanked me, punctuated with a smiley-face emoji.

Giuliani runs a global cybersecurity firm, but his technological gaffes have become legendary. After texting me the password, an NBC report revealed that around the same time he’d butt-dialed a journalist and accidentally left a voicemail documenting his discussion with an associate about how to get cash. “You know,” Giuliani says at the beginning of the recording, “Charles would have a hard time with a fraud case ’cause he didn't do any due diligence.”

At the time it was unclear who “Charles” was, but I might have found him. And I found him, through all things, in Giuliani’s attempt to straighten up his media act.

A few weeks into my conversations with Giuliani, I got a call from a tidewater-area Virginia number. A polite young woman told me I’d been calling Rudy on “an office line,” and she wanted to know my name and affiliation. I told her, then looked her up: Christianné Allen.

The connections between Allen and Giuliani at first struck me as superficial: Why did Giuliani — a former U.S. attorney and mayor of New York City, the president’s personal lawyer and an untamed media presence, to put it charitably — hire a wildly underqualified pseudo-evangelical Turning Point USA social media personality to clean up his comms operations?

The first red flag was Allen’s experience. She styles herself as a jet-setting, gun-porning, right-wing Instagram influencer. Her online bios say she was a “spokeswoman” for the 2016 Trump campaign, but in reality she was a teenage intern with a thin record of spokeswomaning. Allen also did social media for the 2018 congressional campaign of far-right Republican long-shot Tim Donnelly, founder of the California Minutemen Party, who didn’t come close to winning even the GOP vote. She volunteered for Virginia Women for Trump, and her bios say she now serves on the finance committee for Trump Victory Committee. (Allen’s LinkedIn omits her work on the Donnelly campaign.)

But her LinkedIn page has an anomaly: A 2016 summer internship Allen landed at a Long Island personal injury firm, a long way from her rural Virginia home.

That personal injury firm is Gucciardo Law, headed by Charles Gucciardo. Last week Giuliani and Gucciardo confirmed to the New York Times that Gucciardo gave $500,000 to the former mayor through Giuliani’s firm, Giuliani Partners, in two payments in September and October 2018. According to Gucciardo’s lawyer, the payments went to Giuliani on behalf of Fraud Guarantee, a company co-managed by Giuliani’s clients Lev Parnas and Igor Fruman. Their work with Fraud Guarantee — whose mission statement is to help their customers “reduce and mitigate fraud” — helped earn them a federal indictment last month.

Gucciardo’s lawyer told the Times the funds were loans convertible into equity in the company. As the Times pointed out, though, Fraud Guarantee doesn’t seem to have any clients or customers, and it’s unclear why someone in Gucciardo’s position — an experienced lawyer — would invest half a million dollars in such a company. Per Gucciardo’s lawyer, he did so because Giuliani was involved, and Giuliani was “the first name in cybersecurity.”

In a conversation, Stephen LaMagna, a lawyer who represents Gucciardo, told me, “Mr. Gucciardo’s investment in the company was and remains a loan pursuant to executed promissory notes.” This means Gucciardo hasn’t been repaid and could sue if he believes he’s been defrauded. Parnas once pursued a similar scam, and still hasn’t paid despite a court ruling against him.

As for Giuliani’s relationship with Gucciardo, he told me, “Charles is a good man. The loan is due in mid 2020 and I am certain it will be honored as a conversion to stock or both or satisfied as he desires.” It is currently not clear whether a Fraud Guarantee public offering is in the works.

“Charles is my friend,” Giuliani added, “and he knows it will be done honorably.”

The first name in cybersecurity may or may not be Giuliani, but the first name in Gucciardo Law, of course, is the same one Giuliani believed would have a “hard time with fraud” in the voicemail: Charles.

Suggested Friends

Strangely enough, we still don’t yet know how Gucciardo, Giuliani, and Parnas all met. The only thing that binds this group other than money is, oddly enough, Christianné Allen.

Facebook posts show Gucciardo met Allen at a 2015 Stanford University law seminar for high school students, where she impressed him. (Allen said in an Instagram story that she “did high school online.”) In the photos posted on Facebook by Gucciardo, Allen appears in the front row of a lecture hall, and then with her arm around Gucciardo’s son.

Allen interned at Gucciardo’s firm the following year, and appeared with him at a pro-Trump event that October at Trump International Hotel in Washington, DC, where Gucciardo gave a lengthy speech.

After Trump’s election, Allen tried to start a combination marijuana business–reality TV show in Nevada with her father, registered at a house. Neither venture bore fruit, but after some travel, Allen attended another Trump fundraiser with Gucciardo at Trump International, held for major donors to the America First PAC in June 2018.

As far as we know, that $100,000-a-head event is the first time the various members of the group seem to have met, at least in public record: the first time Giuliani met Parnas; the first time Gucciardo met Parnas; the first time Giuliani met Gucciardo; and apparently the first time Giuliani was photographed with Allen. (Giuliani told me in a text he’s “known of” Gucciardo for a while.)

Parnas’s son, Aaron, was also present. (Aaron was the first person to comment on Allen’s Facebook post announcing her job with Giuliani.)

After the Trump International fundraiser, Gucciardo donated $50,000 to America First. The next month Parnas and Fruman traveled with Gucciardo to Israel, where they were photographed with Anthony Scaramucci, who said Parnas and Fruman were trying to “rope people into their game” on the trip. On his return, Parnas pledged Giuliani the $500,000 payment, but, needing cash, got Gucciardo to front the money. According to the New York Times, this money secured Parnas’s relationship with Giuliani, which as far as we know was about three months old.

Parnas and Fruman ramped up their work for Giuliani. Photographs from November show Giuliani and Parnas with Gucciardo on a trip to Ukraine. Parnas and Fruman made some more trips abroad — including reportedly trying to shake down a powerful oligarch — and then, in April of this year, Gucciardo was given a "friend of Zion" award at a Times Square event that also honored Parnas and Fruman. Giuliani posed onstage for pictures.

Allen announced her new job with Giuliani in late September, but Giuliani’s Instagram account suggests she’d been involved in his social media operation since at least the end of August. An Internet Archive search shows that at some point between September 2 and 5 Giuliani’s Twitter account deleted an August 24 photo of Gucciardo, captioned, “A wonderful boat ride with Captain Charles Gucciardi.A great person.” [sic]

Allen joined Giuliani on a boat with Daily Caller contributors in July, after which they dined at Scaramucci’s restaurant.

And then there are the drugs. Allen’s Nevada marijuana business, Discovery Club, has since dissolved, and the alleged reality show, “High Stakes,” never got made. (She did do a podcast interview about the experience, however, which has since been deleted.)

Coincidentally, though, the Parnas and Fruman indictment alleges the two of them, with the help of two associates, tried to finagle illegal pot licenses for a Russian billionaire via donations to political candidates who could influence marijuana laws in Nevada, New York, and Florida. Their indictment alleges they started the effort when Gucciardo made the $500,000 loan to Fraud Guarantee. Around that same time, Gucciardo, who lives on Long Island, donated to a PAC supporting Florida GOP gubernatorial candidate Ron DeSantis. Parnas also donated to DeSantis, who upon winning the election legalized smokable medical marijuana. The governor has since returned Parnas’s donation.

It’s unclear how Allen came to Giuliani, whether through Gucciardo or Parnas or some other happy coincidence. No matter the path, it seems Giuliani and Allen by omission both tacitly acknowledge that these connections, if uncovered, might cause problems, but for whatever combination of reasons, Giuliani offered her the job, and Allen took it. Rudy's Twitter voice has been noticeably different since he brought her on, however, evincing that trademark Charlie Kirk-esque snark, grammar slightly improved, and penned in a young Trumpublican style. She’s injected a freshness that I imagine Giuliani finds revitalizing in such a stressful time, for better or worse. The old-school Giuliani brand, the savvy swinger of smoke-filled, backroom deals, the man who guided our greatest city through its worst tragedy, has given way to tossed-off lines imposed Powerpoint-style over a digital American flag.

This all reflects a larger theme in Trump world: As it becomes increasingly untenable for serious people to associate themselves with Trump, their world gets smaller, and the tried and true allies who hang on find themselves with fewer and fewer options for top-tier advisers, lawyers, campaign staff, and so on. It’s hard to quench the thirst for loyalty in the middle of such a drought, but, as the saying goes, there’s honor among thieves. They might at first seem like odd couples, but they tend to play in the same sandbox, by the same rules.