Trump’s Campaign of Humiliation Against Ron DeSantis

Donald J. Trump plumbed new depths of degradation in his savage takedown of Gov. Ron DeSantis of Florida, a yearlong campaign of emasculation and humiliation that helped force one of the party’s rising stars out of the presidential race after just one contest and left him to pick up the pieces of his political future.

In front of enormous rally audiences, Mr. Trump painted Mr. DeSantis as a submissive sniveler, insisting that he had cried and begged “on his knees” for an endorsement in the 2018 Florida governor’s race.

In a series of sexually charged attacks, Mr. Trump suggested — without a shred of proof — that Mr. DeSantis wore high heels, that he might be gay and that perhaps he was a pedophile.

He promised that intense national scrutiny would leave Mr. DeSantis whining for “mommy.”

Mr. DeSantis shied from fighting back, which only inflicted more pain on his campaign. The governor had portrayed himself as one of the Republican Party’s fiercest political brawlers, but he pulled his punches in the most important race of his life.

Now he is both defeated and debased. His departure from the race on Sunday was a far fall from grace after opening his campaign as the heir apparent in a Trumpified Republican Party. Rehabilitating that reputation as he considers his next political move will require plenty of repair work with donors and Republican voters, thanks to Mr. Trump’s ruthless parade of insults over 242 days on the campaign trail.

“I don’t care if he’s a Republican,” Mr. Trump said of his belittlement of Mr. DeSantis at a November gathering of the Republican Party of Florida — the governor’s home turf. “We hit him hard, and now he’s like a wounded falling bird from the skies.”

But even more crushing was Mr. DeSantis’s response, or lack thereof.

After releasing a campaign video in 2022 that made him out to be a political fighter sent from the heavens, he appeared either unwilling or unable to swing back at Mr. Trump or go on the attack. Even Mr. Trump’s aides were surprised that the DeSantis campaign did not go harder at the former president on issues where he might be vulnerable with conservatives, like abortion.

And the prickly nature of Mr. DeSantis’s personality, which could manifest itself in an awkward mix of detachment, moodiness and facial tics, amounted to an irresistible target for Mr. Trump, who seemed to relish bullying Mr. DeSantis as if he were stuffing a freshman in a high school locker.

Still, Mr. DeSantis remains popular in his home state, and beyond Florida he’s viewed relatively favorably. As a presidential candidate, he needed to succeed where every Republican before him had failed: prying loyal Trump supporters away from the former president without alienating them.

Mr. Trump has long trampled over the boundaries of generally accepted political behavior, relentlessly pushing the racist “birther” lie about President Barack Obama and urging supporters to lock up Hillary Clinton. But his campaign hit new levels of cruelty against a fellow Republican.

The missives were often led by Mr. Trump’s chief spokesman, Steven Cheung, who leaned into his background as a public relations operative for the Ultimate Fighting Championship to deliver brutal slams with the force of the sport’s suffocating guillotine chokehold.

In November, Mr. Cheung told The Wall Street Journal that in Iowa, Mr. DeSantis would face “unimaginable pain that he’s never felt before in his life.”

In a news release, he cast doubt on Mr. DeSantis’s masculinity, saying that he walked like “a 10-year-old girl who had just raided her mom’s closet and discovered heels for the first time.”

Mr. Cheung also referred to the Florida governor as a “desperate eunuch,” questioned why Mr. DeSantis would “cuck himself” in front of the entire country — sexual slang that implies weakness in a man — and accused him of searching for “new sugar daddies” to fund his campaign. He called Mr. DeSantis a “disloyal dog.”

Mr. DeSantis fought back with a more traditional approach.

His campaign rolled out a “Trump Accident Tracker” in a daily email to the news media that highlighted Mr. Trump’s missteps on the trail. He criticized Mr. Trump’s “juvenile insults,” saying voters did not like them. (The eruption of laughter inside Trump rallies suggested otherwise.)

Mr. DeSantis eventually tried to up his game.

Responding to accusations that he wore lifts in his cowboy boots to appear taller, Mr. DeSantis questioned Mr. Trump’s manhood.

“If Donald Trump can summon the balls to show up to the debate, I’ll wear a boot on my head,” Mr. DeSantis said.

The line did not seem to land. Mr. DeSantis himself has admitted that, unlike Mr. Trump, he is “not an entertainer.”

At the same time, pro-Trump online influencers formed a troll army pumping out content like videos showing a man with Mr. DeSantis’s face being kicked in the groin. In comparison, Mr. DeSantis’s online operation proved haplessly inept.

The differing approaches stemmed, in part, from a fixation on Mr. DeSantis inside Trump headquarters, where animosity for the governor ran high.

Not only was Mr. Trump incensed by what he viewed as a striking lack of loyalty from Mr. DeSantis, but the Trump campaign also includes former DeSantis campaign aides who had been fired or felt otherwise mistreated by the Florida governor, including Susie Wiles, one of the former president’s closest confidantes. Many still had axes to grind.

“Bye, bye,” Ms. Wiles posted on Sunday on social media about her erstwhile boss, who had tried to blackball her from Republican politics.

The quick endorsement from Mr. DeSantis on Sunday may help salve some of those wounds. Hours later, Mr. Trump vowed that he would retire the “DeSanctimonious” nickname, and his allies began posting messages welcoming Mr. DeSantis back into the Trump fold.

But aides said that Mr. Trump and Mr. DeSantis had still not talked.

Asked about whether the two men could repair their relationship, Mr. Cheung held his fire.

“We’re focused on New Hampshire,” he said.

Ken Bensinger contributed reporting from Los Angeles.