In early May, as Gov. Ron DeSantis prepared to run for president, about a dozen conservative social media influencers gathered at his pollster’s home for cocktails and a poolside buffet.
The guests all had large followings or successful podcasts and were already fans of the governor. But DeSantis’ team wanted to turn them into a battalion of on-message surrogates who could tangle with Donald Trump and his supporters online.
For some the gathering had the opposite effect, according to three attendees who spoke on the condition of anonymity because they did not want to damage their relationships with the governor or other Republican leaders.
DeSantis’ advisers were defensive when asked about campaign strategy, they said, and struggled to come up with talking points beyond the vague notion of “freedom.” Some of the guests said they left doubtful that the DeSantis camp knew what it was in for.
Four months later, those worries seem more than justified. DeSantis’ hyper-online strategy, once viewed as a potential strength, quickly became a glaring weakness on the presidential trail, with a series of gaffes, unforced errors and blown opportunities, according to former staff members, influencers and commentators.
Even after a recent concerted effort to reboot, the campaign has had trouble shaking off a reputation for being thin-skinned and mean-spirited online, repeatedly insulting Trump supporters and alienating potential allies.
Some of its most visible efforts — including videos employing a Nazi symbol and homoerotic images — have turned off donors and drawn attention away from the candidate. And despite positioning itself as a social media-first campaign, it has been unable to halt the cascade of internet memes that belittle and ridicule DeSantis.
DeSantis is polling in a distant second or even third place. Like the rest of its rivals, his campaign has often failed to land meaningful blows on Trump, who somehow only gains more support when under fire.
But as surely as past presidential campaigns — such as Bernie Sanders’ and Trump’s — have become textbook cases on the power of online buzz, DeSantis’ bid now highlights a different lesson for future presidential contenders: Losing the virtual race can drag down an in-real-life campaign.
“The strategy was to be a newer, better version of the culture warrior,” said Rob Stutzman, a Republican strategist. “But they did it to the exclusion of a lot of the traditional campaign messaging.”
The DeSantis campaign disputed that it was hurt by its online strategy but said it would not “relitigate old stories.”
“Our campaign is firing on all cylinders and solely focused on what lies ahead: taking it to Donald Trump and Joe Biden,” said Andrew Romeo, a campaign spokesperson.
Pudding fingers
The trouble began when DeSantis rolled out his campaign in a live chat on Twitter, the servers crashed, booting hundreds of thousands of people off the feed and drawing widespread ridicule.
When his campaign manager at the time, Generra Peck, discussed the fiasco at a meeting the next morning, she claimed the launch was so popular that it broke the internet, according to three attendees, former aides who insisted on anonymity for fear of reprisal for discussing internal operations.
Each recalled being flabbergasted: Senior staff members seemed convinced that an embarrassing disaster had somehow been a victory.
Peck exercised little oversight of the campaign’s online operations anchored by a team known as the “war room,” according to the three former aides. The team consisted of high-energy, young staffers who spent their days scanning the internet for storylines, composing posts and dreaming up memes and videos they hoped would go viral.
At the helm was Christina Pushaw, DeSantis’ rapid response director. Pushaw has become well known for her extreme online approach to communications, including a scorched-earth strategy when it comes to critics and the press. As the governor’s press secretary, she frequently posted screenshots of queries from mainstream news outlets on the web rather than responding to them and once told followers to “drag” — parlance for a prolonged public shaming — an Associated Press reporter, which got her temporarily banned from Twitter.
Long before the presidential run was official, Pushaw and some others on the internet team — often posting under the handle @DeSantisWarRoom — aggressively went after critics, attacking the “legacy media” while promoting the governor’s agenda in Florida.
At first, they conspicuously avoided so much as mentioning Trump and appeared completely caught off guard when, in March, pro-Trump influencers peppered the internet with posts that amplified a rumor that DeSantis had once eaten chocolate pudding with his fingers.
The governor’s campaign dismissed it as “liberal” gossip, even as supporters of Trump began chanting “pudding fingers” at campaign stops, and a pro-Trump super political action committee ran a television ad that used images of a hand scooping up chocolate pudding.
The episode looks like little more than childish bullying, but such moments can affect how a candidate is perceived, said Joan Donovan, a researcher at Boston University who studies disinformation and wrote a book on the role of memes in politics.
The best way to counter that kind of thing is to lean into it with humor, Donovan said. “This is called meme magic: The irony is, the more you try to stomp it out, the more it becomes a problem,” she said.
The DeSantis campaign’s muted response signaled open season: Since then, the campaign has failed to snuff out memes mocking the governor for supposedly wiping snot on constituents, having an off-putting laugh and wearing lifts in his cowboy boots.
Pink lightning bolts
Attempts to go on the offensive proved even further off the mark. In June, the war room began creating highly stylized videos stuffed with internet jokes and offensive images that seemed crafted for a far-right audience.
One video included fake images of Trump hugging and kissing Anthony Fauci — a dig at the former president’s pandemic response. Some conservatives were offended, calling the post dishonest and underhanded.
“I was 55/45 for Trump/DeSantis,” Tim Pool, whose podcast has 3 million subscribers across multiple YouTube channels, wrote in response to the video. “Now I’m 0% for DeSantis.”
Another video cast Trump as too supportive of LGBTQ rights and mashed up images of transgender people, pictures of DeSantis with pink lightning bolts shooting out of his eyes and clips from the film “American Psycho.”
That was followed by a video that included a symbol associated with Nazis called a Sonnenrad, with DeSantis’ face superimposed over it.
Although many of the videos were first posted on third-party Twitter accounts, they were made in the war room, according to two former aides and text messages reviewed by The New York Times.
As public outrage grew over the Sonnenrad video, the anonymous account that posted it — called “Ron DeSantis Fancams” — was deleted. The campaign took steps to rein in the war room, according to two former aides. And although the video was made collaboratively, a campaign aide who had retweeted it was fired.
The online controversy roiled the rest of the campaign. In early August, aerospace tycoon Robert Bigelow, who had been by far the largest contributor to Never Back Down, the pro-DeSantis super PAC, said he would halt donations, saying, “Extremism isn’t going to get you elected.”
Money from many other key supporters of DeSantis has also dried up, including from billionaire hedge fund manager Kenneth Griffin.
Terry Sullivan, a Republican political consultant who was Sen. Marco Rubio’s presidential campaign manager in 2016, said the bizarre videos amounted to a warning sign for donors that DeSantis’ campaign was chaotic, undisciplined and chasing fringe voters.
“Most high-dollar donors are businesspeople,” Sullivan said. “Nobody wants to buy a burning house.”
Switching course
The campaign has lately tried to switch course. Under the direction of James Uthmeier, who replaced Peck as campaign manager in August, it has shifted to a more traditional online strategy.
“I should have been born in another generation,” said Uthmeier, 35, in an interview. “I don’t even really know what meme wars are.”
The campaign has more closely aligned its online messaging with the rhetoric DeSantis delivers on the stump. It has installed new oversight over its social media team and more closely reviews posts from the DeSantis War Room account, according to a person familiar with the campaign.
It also has dialed down the often combative tone set by many of its influencers and staff members and scaled back its production of edgy videos.
“For a while, they struck me as being more interested in winning the daily Twitter fight than in winning the overall political campaign,” said Erick Erickson, an influential conservative radio host.
But now, he said, DeSantis finally seemed to be running for “president of the United States and not the president of Twitter.”
