A text thread from October 11. Photo: Courtesy of Olivia Nuzzi

Everyone who texts with Rudy Giuliani knows the hands of fate control the fingertips. Digital communication with President Trump’s 75-year-old personal attorney is a delicate exercise in optimism and patience. Or, as one longtime Giuliani associate phrased it, “This is a little bit like a baby with a hammer, or a monkey with a typewriter.”

This fall, as Giuliani has emerged as a central figure in the impeachment inquiry, his clumsy phone comportment has often become worldwide news, adding extra absurd wrinkles to the already absurd saga of a quid pro quo in Ukraine and raising questions about how a chronic butt-dialer who wears his AirPods upside down could be a White House cybersecurity adviser.

There was the time he accidentally called NBC’s Rich Schapiro and left a voice-mail in which he could be heard alleging that Joe Biden’s family was corrupt. Or the time he accidentally called Schapiro again and left a voice-mail that documented a conversation about overseas business in which he said, “We need a few hundred thousand.” Or when he texted Axios’ Jonathan Swan a voice recording in which he could be heard “talking to a guy,” as Swan described it. “I couldn’t make any sense of it or figure out how he managed to text me a recording inadvertently.” Or when he mistakenly texted what appeared to be a password to reporter Roger Sollenberger.

Giuliani is probably the most accessible star of an international political scandal in modern history, open to corresponding directly with almost anyone, anytime, telling them information that may be repetitive or mundane but that just as likely may be a real development in the story that determines the future of this presidency. (Trump, too, is known for compulsively using his phone, but to make phone calls, not text.) On big news days in Washington, it can feel like everybody is texting with Giuliani at the same time — and sometimes it’s because we are. Or we sure hope it’s Giuliani we’re talking to. “He changes numbers somewhat randomly,” one White House reporter said, “so you never really know if you’re texting the right number.” Personally, I have half a dozen numbers for Giuliani saved. Which one is most reliable today? Only one way to find out, really!

Fortunately, there are tells. Giuliani uses iMessage, and, like so many men over 50 who work for Trump, he has read receipts enabled and often uses iMessage’s reaction feature to like questions sent to him instead of providing an answer. Just as often, he likes his own messages. On one occasion, he scrolled back an entire day in our conversation to add a like to a message of his own. He didn’t explain why. “It’s unclear what it means,” the White House reporter said before recounting a similarly odd, like-related experience. “He once liked a question I sent him about him being accused of illegal lobbying, and then he didn’t respond to the question about lobbying.”

A second White House reporter added, “Every now and then, he might send some variety of the smiley-face emoji, but he’s much more likely to like his own texts. I remember one time he gave his own text a thumbs-down but then promptly switched it to a thumbs-up.” On the subject of emoji: During a news cycle that called into question the state of his employment as Trump’s personal lawyer, I texted back and forth with Giuliani for the duration of my flight from New Hampshire to Washington. When I asked him whether he’d be surprised if Trump ended up throwing him under the bus, he texted back, “Stop,” with the stop-sign emoji (a deep cut on the emoji keyboard).

Then there are weirder events. “He sometimes sends text messages that are clearly not meant for you,” the first White House reporter said. “For example, he once sent me a picture of him smoking a cigar on a golf cart.” The second White House reporter added, “I’ve definitely woken up to a missed FaceTime call, which I can only hope was inadvertent.”

Recently, Giuliani created a group chat with me, Sinclair host Eric Bolling, CNN senior political analyst John Avlon, and two numbers I didn’t recognize to send an unsolicited statement from his attorney. Another time, I woke up in the middle of the night to a long and angry text from Giuliani, sent at 2:46 a.m., containing an Apple News link to a story I’d written about the former veep. “Joe Biden is a good man? Are you so blinded by your own biases. Everywhere he was named a Point Man by Obama his family made millions,” he wrote. I tried to respond, but my text went through to his email address instead of as an iMessage. Had he blocked me? I sent him an email asking if we could talk, and he responded in the middle of the night a few days later. He said I had “too many biases to overcome.” Others have had similar experiences. A fourth reporter recalled being blocked by Giuliani after his new communications director, Christianné Allen, answered his phone for the first time. “I’ve found that the best way to get Giuliani to respond is to push his buttons a bit,” this reporter said. “Though it’s been a lot harder for me to reach him lately.”

I asked the White House if anyone over there is concerned about someone so erratic having access to the president’s secrets. In response, White House press secretary Stephanie Grisham said, “Mr. Giuliani is a private citizen, and as such, we have no comment on this.”

It would be impossible to honestly discuss Giuliani’s communication habits without discussing his habits more generally. It’s well documented that he’s a night owl and a creature of cigar bars in Manhattan and Washington, and rumors have long swirled about his drinking. (“I’m not drinking for lunch,” Giuliani told Politico after MSNBC’s Joe Scarborough accused him of drinking too much. “I may have a drink for dinner. I like to drink with cigars.”)

As Giuliani has transformed before our eyes in the Trump era, longtime friends, associates, and observers have asked, with as much concern as contempt, What happened? The question and the theories it has given rise to — some kind of decline or dependence — seem as much about denial as anything else, like a refusal to accept that a person of sound mind would choose to behave this way, to defend this president in this manner, to throw away decades of goodwill after a life in public service, and for what? Proximity to power? All the wrong kind of attention?

“I think the reality is people perceive a decline because they’re witnessing him being extremely aggressive, persistent, and vocal about a political issue that has polarized the country,” former NYPD commissioner Bernard Kerik told me. “I think people just see his aggression as a decline. But I have to tell you, in sitting with him and going through these details, names, times, places, all the stuff that he has collected since last year, I can tell you he doesn’t miss a beat. There is no decline. It’s almost like he has reverted back to his prosecutorial mind-set.”

A second longtime Giuliani associate agreed with Kerik. “I’ve been around him a lot. I haven’t seen him ever drink more than two drinks,” this person said. The associate called questions about Giuliani’s state of mind unfair and insisted that he’s as “razor sharp” as ever. And besides, this person added, Giuliani “takes the attorney-client privilege very, very seriously” and doesn’t talk about his communications with the president over text or email. When reached for comment, Giuliani replied: “Garbage your publication cannot be counted on to report fairly on this salacious stupidity … I am a high functioning human being able to outwork people half my age. Compared to Biden and Pelosi, I’m a phenom.”

Still, some people who communicate with him believe Giuliani’s behavior can be almost predictable — if you know what you ought to try to predict. “I usually try getting him around eight, nine o’clock. After that, he’s often too deranged,” the third White House reporter said. “You want him to be loose but not completely kind of unmoored.”

This reporter said that the process began to feel fraught and unseemly — not in a Sam Nunberg, Should we be talking to this guy right now? kind of way, but because Giuliani is “the most unreliable narrator ever.”

“There’s almost no point in talking to him, but he’s objectively newsworthy and in a position of great power. So you’ve gotta talk to him, but most of the time, it’s like a Breitbart comments page. You’re just dealing with a troll. It’s funny, but after a while, it’s like, what’s the point?”

*This article appears in the November 25, 2019, issue of New York Magazine. Subscribe Now!