How Ron DeSantis Lost the Internet

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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.

Pudding Fingers

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.

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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.

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