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.
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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.
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