Donald Trump and Justin McConney, then Trump's social media manager, at Facebook's New York headquarters in May 2015, just a month before Trump announced his presidential campaign. | Courtesy of Justin McConney White House 'Oh, no': The day Trump learned to tweet Trump's first social media adviser reveals the full inside story of how he guided his ex-boss from Luddite to Twitter addict.

The content of the tweet @RealDonaldTrump posted on the night of Feb. 5, 2013, was bland: a simple thank you to the actress Sherri Shepherd for flattering comments she’d made about Trump on television.

Thanks @SherriEShepherd 4 your nice comments today on The View. U were terrific! — Donald J. Trump (@realDonaldTrump) February 6, 2013

But its implications were historic.


When Trump’s young social media manager saw the tweet, he was perplexed. He typically typed and sent Trump’s tweets for the boss, but in this case he hadn’t. He did recall that Trump had been spending a lot of time in his office lately playing around with a new Android smartphone.

The next morning, the handful of staffers with access to the boss’ account told the social media manager, Justin McConney, that they had not sent it either.

That’s when it dawned on him: Donald Trump had tweeted on his own for the first time.

"The moment I found out Trump could tweet himself was comparable to the moment in 'Jurassic Park' when Dr. Grant realized that velociraptors could open doors," recalled McConney, who was the Trump Organization’s director of social media from 2011 to 2017. "I was like, 'Oh no.'"

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At the time, no one — not even McConney himself — could grasp what was to come. Now, in rare on-the-record interviews with POLITICO, McConney, who left the Trump Organization last year, has laid out the story of Trump’s journey from an old-school Luddite to a social media maven.

While the president's Twitter use has been covered extensively, this is the first time the inside story of how Trump conquered social media has been told in full. McConney’s account sheds new light on how Trump built his approach to the medium that won him the presidency with firsthand insight that predates that of any of Trump’s current White House or campaign aides.

He also has a warning for the president and his social team: Up your game if you want to stay competitive in 2020.

"He needs to return to engaging directly with his fans again," advised McConney, now a social media consultant, who said Trump should look beyond Twitter and pay more attention to other platforms. The president’s Instagram account has become particularly bland and impersonal, he warned, and he wondered why Trump had not been using the platform’s popular "Stories" function, which other politicians — including Trump’s potential 2020 Democratic rival Beto O’Rourke — have used to great effect.

"He should be live streaming from the Oval Office," McConney said.

Donald Trump, Justin McConney and Christian Bale together in Trump Tower in October 2011, when Bale was filming "The Dark Knight Rises." | Courtesy of Justin McConney

That was not a possibility anyone envisioned in January 2011, when a couple of Trump Organization executives asked McConney, then a 24-year-old film school graduate and the son of the company’s controller, whether he could pull together a video to be shown at a weekend meeting of Trump’s golf course managers at Mar-a-Lago.

McConney jumped at the chance. But as he began editing, he was surprised to learn the Trumps did not have a YouTube channel. Instead, he had to trudge to a closet in Trump Tower full of DVDs and old VHS tapes featuring the family and their properties. The video McConney stitched together featured rock music over a montage of clips focused on Trump the man, rather than on the company’s scenic properties.

It was not what the executives had been expecting. But Trump himself liked this approach. A lot.

The following Monday, McConney’s phone rang. It was a Trump Organization executive: The boss wanted the Golf Channel to air his video on the upcoming season of “Donald J. Trump's Fabulous World of Golf.” He also wanted to see McConney in his office immediately.

McConney, who initially protested that he was not wearing a suit, headed over to Trump Tower in jeans.

McConney had met his father’s boss in passing a handful of times over the course of his childhood, but to be called to a private meeting with him was a thrill. In Trump’s office on the 26th floor, the mogul was staring at his laptop, watching an unaired intro for the upcoming season of “The Apprentice.” Trump asked McConney what he thought of the clip.

McConney quickly pivoted the conversation from television to the potential of social media. Trump seemed vaguely interested. His company had dabbled in the area, but Trump had little understanding of it.

"I’ve heard of that," McConney recalled Trump saying. “Isn’t that what [then-President Barack] Obama used?"

Jimmy Fallon, McConney and Trump at "The Tonight Show" in September 2015. | Courtesy of Justin McConney

The @RealDonaldTrump Twitter account had existed since 2009 but had been broadcasting bland, promotional fare, like "Wishing everyone a very Happy Holiday Season." At first, the tweets had been authored mainly by marketing specialist Peter Costanzo, who set up the account to help Trump promote his 2009 book, "Think Like a Champion," and oversaw it for its first several months of existence. Then Trump Organization staff took over. In all of 2010, it had tweeted only 142 times.

McConney suggested that Trump get on YouTube and retool his Twitter presence.

"He seemed to be familiar with the names but not what you could do with them," McConney recalled of the platforms. By the time he walked out of Trump’s office, he had a job.

Working out of the Trump Organization’s lunchroom — the company did not know where else to put him — McConney began extolling the Internet’s virtues to Trump and his family. And he argued that Trump should transfer his freewheeling approach to the world’s most unregulated public arena.

"I wanted the Donald Trump who is on Howard Stern, commenting on anything and everything," he said.

At the outset, this was accomplished with videos of Trump speaking straight to camera from his desk at Trump Tower, which were then posted to YouTube and linked to in tweets.

Trump, a creature of television and the tabloids, remained skeptical of social media exposure for its own sake. But his thinking began to change when McConney showed him how social media could translate into the kind of traditional media coverage the mogul had spent decades cultivating.

A turning point came in the spring of 2011, when Sarah Palin, then considering her own run for president, joined Trump for a pizza lunch in Manhattan. Media coverage of the outing fixated on Trump’s fork-and-knife pizza-eating technique. McConney convinced Trump to record a video blog explaining his decision.

To the mogul’s delight, his explanation — “This way you can take the top of the pizza off so you’re not just eating the crust. I like to not eat the crust so we can keep the weight down” — generated a bonus round of coverage from the likes of Time and Gawker.

“That's when he was sold on the concept of social media," McConney recalled.

Trump, used to haggling with reporters and TV producers, loved the instant gratification — and the control over his own image.

He also loved the way it allowed him to throw verbal punches. He demanded that the young rapper Mac Miller, who had recently released a hit song titled “Donald Trump,” send him royalties (a point he would harp on for the next two years.) He picked fights with Rosie O’Donnell and Lawrence O’Donnell.

And, as he flirted with a 2012 presidential run, he got more political. In mid-2011, he tweeted about Anthony Weiner’s obscene-photo scandal and began offering thoughts on the budget, like “The Debt Limit cannot be raised until Obama spending is contained.” Such digs at Obama became increasingly common.

McConney stands back as Trump films his response to the Ice Bucket Challenge in August 2014. | Courtesy of Justin McConney

By the end of the year, Trump had sent 744 tweets in 12 months — five times his 2010 total. He was only just getting started.

He began acting like the director of his own mini-media empire, huddling with McConney first thing each morning to talk about ideas and plan output for the day. “They were kind of like editorial meetings," McConney said.

Even as the mogul embraced digital media, he did so in the most analog way possible. He had McConney print out his Twitter mentions, and he would use Sharpie pens to scribble responses, which McConney would then type up and tweet out. After appearing at events, Trump, who remained distrustful of anything he saw only on a screen, had McConney print out 8x10 glossy photos of him for his signoff before they were posted online.

“He was very old school back then,” McConney said. “He was not someone who really used computers or went on the internet very much.”

While Trump did not know much about new technology, he “knew PR and he knew news cycles very well.” If some major news broke throughout the day, Trump would call in McConney to plot out a way to comment on it quickly, even if it meant interrupting his meetings. “It was like new meets old,” McConney said of the collaboration.

The embrace did not happen all at once. Even after he recognized the potential use social media had to earn traditional media, he balked at using his appearances on traditional media to build his online following.

Trump resisted McConney’s suggestion that he do so, grumbling that touting his Twitter handle in television appearances would look dumb. By early 2012, he had an assistant call television networks to make sure they plugged the handle on the screen whenever he appeared. By that spring, @RealDonaldTrump was being displayed on-screen during “The Apprentice.”

Trump was now tweeting at a pace of 10 times a day. He began phoning in tweets to McConney at all hours, dictating the precise placement of dashes and exclamation points. At first, the calls would come from Melania, who saved McConney’s number before her husband did, and would hand her husband the phone after saying hello.

The calls sometimes came after midnight, other times at dawn. Trump once called at 2 a.m. on a weeknight and demanded to know what McConney was doing up at that hour. McConney said he could ask Trump the same thing. Trump ignored that response and told McConney he’d see him in his office first thing in the morning.

One call came on the Sunday before Memorial Day when McConney was at a Wegman’s in New Jersey.

“George Will just hit me on TV. I have to hit back,” Trump roared after the conservative commentator had appeared on ABC’s “This Week.” “Write this down and tweet it out immediately,” he instructed.

Trump would call McConney on a Saturday to order up a tweet — then linger on the line for 20 minutes as others popped into his head, with Melania offering thoughts in the background. "'Dude,’ I’m thinking in my head, ‘It's the weekend,’" McConney recalled.

After Obama name-checked Trump in his first debate with Mitt Romney that fall, McConney suggested that Trump live-tweet the second presidential debate, which he did, by phoning in his occasional musing to McConney. “Because Obama was so pathetic in the first debate, tonight's audience will be humongous--people want to see if he is for real,” he opined.

As the pace of Trump’s tweeting continued to accelerate, he enlisted other tech-savvy staffers, like his assistant Meredith McIver, to publish his tweets whenever McConney was not on hand. Even so, McConney could barely keep up.

Then in November, on a flight to a Trump resort in Miami, Trump asked McConney whether he preferred iPhones or Androids. When McConney indicated the former, Trump responded, “But the screens are much bigger on the Android.” Trump soon had one of his own, and the following February, he began tweeting for himself.

The shackles were now totally off. In 2013, he tweeted more than 8,000 times. From time to time, McConney would advise against individual tweets Trump proposed sending. Often, he would walk away from a conversation believing Trump had been dissuaded, only to see the tweet appear online 10 minutes later.

That month, Trump live-tweeted the Oscars from his phone, offering thoughts like, “Django Unchained is the most racist movie I have ever seen, it sucked!"

Trump and McConney continued to experiment with other social media, including Instagram. But Trump was hooked on tweeting.

When he entered the Republican primary field in 2015, the strategy the pair honed together became an invaluable political weapon. Drawing from the lessons of the past four years, Trump used outrageous tweets to earn traditional media coverage — as his better-qualified opponents struggled, mostly in vain, to grab their fair share of attention.

In the campaign’s early days, McConney continued to lend a hand. He cut 15-second Instagram attack ads, many of them needling Jeb Bush, earning plaudits for the novel format. But McConney was still a film school grad at heart and had little interest in politics. He also found himself marginalized by Trump’s first campaign manager, Corey Lewandowski, who favored Dan Scavino, now White House director of social media, according to two sources familiar with the situation.

McConney, now 32 and working as a freelance consultant, stayed on at the Trump Organization until late 2017. Now that he has stopped working there, he said, he felt free to answer queries from a reporter and share the full story of his collaboration with Trump, as well as to air his critiques of the president’s social presence.

McConney said some of Trump’s social media edge has faded since he assumed the presidency. He argued that Trump’s social media accounts rely too heavily on footage of rally crowds and the president boarding planes. He said Trump’s feeds should include more exclusive content that generates positive media coverage.

He also advised that Trump — whose Twitter feed is now dominated by angry rants about the “fake news” media and special counsel Robert Mueller’s “WITCH HUNT!” — lighten up.

Trump, he said, "should go back to having more of a sense of humor about himself.”

CORRECTION: This story has been updated to correct the spelling of Meredith McIver's name.