In early May, as Gov. Ron DeSantis of Florida prepared to run for president, about a dozen right-wing 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 Mr. DeSantis’s team wanted to turn them into a battalion of on-message surrogates who could tangle with Donald J. Trump and his supporters online.
For some, however, 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.
Mr. DeSantis’s 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 at the meeting, which has not previously been reported, left doubtful that the DeSantis camp knew what it was in for.
Four months later, those worries seem more than justified. Mr. DeSantis’s 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 with ties to the campaign and right-wing commentators.
Even after a recent concerted effort to reboot, the campaign has had trouble shaking off a reputation for being thin-skinned and meanspirited 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 much-needed 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 Mr. DeSantis.
These missteps are hardly the only source of trouble for Mr. DeSantis, who is polling in a distant second place. Like the rest of its rivals, the DeSantis campaign has often failed to land meaningful blows on Mr. Trump, who somehow only gains more support when under fire.
But as surely as past presidential campaigns — such as Bernie Sanders’s and Mr. Trump’s — have become textbook cases on the power of online buzz, Mr. DeSantis’s 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 “re-litigate 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 spokesman.
The trouble began immediately. When Mr. 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 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 at the apparent disconnect: Senior staff members seemed convinced that an embarrassing disaster had somehow been a victory.
Ms. Peck exercised little oversight of the campaign’s online operations, which were anchored by a team known internally as the “war room,” according to the three former aides. The team consisted of high-energy, young staffers — many just out of college — who spent their days scanning the internet for noteworthy story lines, composing posts and dreaming up memes and videos they hoped would go viral.
At the helm was Christina Pushaw, Mr. DeSantis’s rapid response director. Ms. Pushaw has become well known for her extremely 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, Ms. 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 Mr. Trump, and appeared completely caught off guard when, in March, pro-Trump influencers peppered the internet with posts that amplified a rumor that Mr. DeSantis had once eaten chocolate pudding with his fingers.
The governor’s campaign dismissed it as “liberal” gossip, even as supporters of Mr. Trump began chanting “pudding fingers” at campaign stops and a pro-Trump super PAC ran a television ad that used images of a hand scooping up chocolate pudding. Seven months later, #puddingfingers still circulates on social media.
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 — and perhaps only — way to counter that kind of thing is to lean into it with humor, Ms. 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 very young, very far-right audience.
One video included fake images of Mr. Trump hugging and kissing Anthony S. Fauci — a dig at the former president’s pandemic response. Many conservatives were offended, calling the post dishonest and underhanded.
“I was 55/45 for Trump/DeSantis,” Tim Pool, whose podcast has three million subscribers across multiple YouTube channels, wrote in response to the video. “Now I’m 0% for DeSantis.”
Another video cast Mr. Trump as too supportive of L.G.B.T.Q. rights and mashed up images of transgender people, pictures of Mr. 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 Mr. DeSantis’s 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 as well as text messages reviewed by The New York Times. Drafts of the videos were shared in a large group chat on the encrypted messaging service Signal, where other staff members could provide feedback and ideas about where and when to post them online.
As public outrage grew over the Sonnenrad video, the anonymous account that posted it — called “Ron DeSantis Fancams” — was deleted. The campaign, which was in the process of laying off more than three dozen employees for financial reasons, 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, the 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 Mr. DeSantis has also dried up, including from the billionaire hedge fund manager Kenneth Griffin.
Terry Sullivan, a Republican political consultant who was Senator Marco Rubio’s presidential campaign manager in 2016, said the bizarre videos amounted to a warning sign for donors that Mr. DeSantis’s campaign was chaotic, undisciplined and chasing fringe voters.
“Most high-dollar donors are businesspeople,” Mr. Sullivan said. “Nobody wants to buy a burning house.”
‘Counterproductive or Annoying or Both’
Videos haven’t been the only problem. The campaign has struggled to build a network of influencers and surrogates that could inject Mr. DeSantis’s message into online conversations and podcasts dominated by supporters of Mr. Trump.
Mr. DeSantis had won over many of those voices in his re-election campaign last year. But repeated attempts at courting additional influencers for his presidential campaign — including the poolside dinner in Tallahassee — fell flat.
Benny Johnson, a former journalist with nearly two million followers on X, Twitter’s new name, resisted overtures from the DeSantis team, remaining a vocal Trump supporter. Chaya Raichik, whose Libs of TikTok account has 2.6 million followers, was at the Tallahassee dinner, according to two attendees, but has remained neutral.
Neither Mr. Johnson nor Ms. Raichik responded to requests for comment. Other influencers said they were repelled by the combative, juvenile tenor of the campaign and unwilling to abandon Mr. Trump, who seemed to be only gaining momentum with each passing week.
“It feels like the campaign has been reduced to little more than bickering with the Trump camp,” said Mike Davis, a conservative lawyer with a large social media following. He said the campaign had reached out to him about being a surrogate, but he declined and has since been turned off by its aggressive tactics online.
“Its tactics are either counterproductive or annoying or both,” he said.
The existing network of DeSantis influencers has presented challenges for the campaign. Online surrogates for Mr. DeSantis have repeatedly parroted, word for word, the talking points emailed to them each day by the campaign, undermining the effort to project an image of widespread — and organic — support.
Last month, for example, three different accounts almost simultaneously posted about Mr. Trump getting booed at a college football game in Iowa. Bill Mitchell, a DeSantis supporter with a large following on X, said the identical posts were coincidental.
“I talk with all of the team members when necessary but other than the daily emails get no specific direction,” he said.
Ending the Meme Wars
The campaign has lately tried to switch course. Under the direction of James Uthmeier, who replaced Ms. Peck as campaign manager in August, the campaign has shifted to a more traditional online strategy.
“I should have been born in another generation,” said Mr. Uthmeier, 35, in an interview. “I don’t even really know what meme wars are.”
Recently, the campaign has more closely aligned its online messaging with the real-world rhetoric Mr. 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, dumping lightning-bolt eyes for more traditional fare.
A video released this week, for example, used clips of television interviews to suggest that Nikki Haley, who has been challenging Mr. DeSantis for second place in Republican polls, had reversed course on whether to allow Palestinian refugees into the United States.
“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, Mr. DeSantis finally seemed to be running for “president of the United States and not the president of Twitter.”
Rebecca Davis O’Brien contributed reporting.