Elon Musk began privately gathering support for Donald Trump’s second presidency long before he tweeted his public endorsement on July 13.

At least five months earlier, Musk made a pitch for Trump at the Palm Beach, Fla., oceanfront mansion of Wendy’s chairman Nelson Peltz, where some of the billionaires and top political strategists who had gathered to discuss 2024 campaign strategy were surprised to see him.

The Feb. 16 event included a number of Trump skeptics: Karl Rove, a former adviser to George W. Bush and a current adviser to hotelier Steve Wynn, argued that the assembled crew should give money to down-ballot candidates and state parties. Another donor urged the crowd to keep helping GOP contender Nikki Haley, according to attendees who spoke on the condition of anonymity to share private conversations.

But Musk, sitting by Peltz at the center of the table, offered an explicitly pro-Trump view, the attendees said. He started by saying he was not a big fan of Trump, but then segued into a lengthy discussion of illegal immigration. While President Biden would allow millions of additional undocumented immigrants to cross America’s southern border - to the detriment of the U.S. economy and American land, Musk asserted - Trump would stop the crossings, he said. He added that a surge of immigrants would fuel a demographic shift that could doom the Republican Party in future elections.

Musk asked people in the room to tell their friends to vote for Trump, saying he had learned from his experience selling Teslas that word-of-mouth promotion was critical. Some people in the crowd shook their heads and winced.

Despite his support, Musk was concerned - along with other potential donors - that Trump might use their money to pay his rising legal bills, the attendees said. Others, he acknowledged, might not want to appear on campaign disclosure forms.

So he suggested giving to an outside group instead. In May, Musk helped launch America PAC, which in a little over a month reported raising $8.5 million, much of it from Silicon Valley. Musk has signaled that he will donate, too, but he denied a report in the Wall Street Journal that he would give the group $45 million a month.

Musk’s presence at the Palm Beach event marked the culmination of a political transformation for the world’s richest person, who has said he favored Biden in 2020. But in the four years since, Musk’s relationship with the Biden administration steadily soured.

Under Biden, the Justice Department and the Securities and Exchange Commission have advanced investigations into Tesla’s marketing of its driver-assistance technologies. The National Highway Traffic Safety Administration announced a recall of almost every Tesla over concerns about driver inattention. The SEC is pursuing a separate investigation into X, formerly Twitter, which Musk purchased in 2022. And Biden has personally ridiculed Musk’s business acumen, once quipping that the best way for NPR to disappear would be for him to buy it, while the White House snubbed Tesla at a high-profile electric vehicle summit in 2021.

A second Trump administration promises a very different environment for Musk, analysts and investors said. Trump could ease Tesla’s regulatory path to delivering a fully autonomous personal vehicle - a goal key to the company’s $700 billion valuation - they said, and dial back federal scrutiny of Tesla and X, as well as a National Labor Relations Board investigation into allegations of harassment at SpaceX.

Meanwhile, SpaceX and Starlink, Musk’s satellite business, stand to gain fresh federal contracts. Clare Hopper, chief of Space Systems Command’s Commercial Satellite Communications Office, said her office already is seeking an additional $12 billion over the next decade for “low-Earth orbit satellites” in anticipation of soaring military demand. That spending could increase further under the Republican platform, which calls for boosting satellite investment and accelerating space exploration onward to Mars.

“In the Biden administration, Musk has been an afterthought at best,” said Dan Ives, an analyst with Wedbush Securities. “In the Trump administration, if he won a second term, Musk would be front and center.”

Trump, for his part, has expressed enthusiasm about his growing alliance with the billionaire. At a recent campaign rally in Grand Rapids, Mich., Trump said of Musk: “We have to make life good for our smart people and he’s as smart as you get.”

The Trump campaign declined to answer questions about Trump’s intentions regarding Musk. Musk did not respond to requests for comment.

The road to Trump

One person who has known Musk for years said he sees Trump as a change agent even as he sometimes disagrees with his approaches and policies. Musk also likes Trump’s pick for vice president, Ohio Sen. JD Vance, a former venture capitalist who moved in the same Silicon Valley circles as Musk, who lobbied for Vance to join the ticket. The person spoke on the condition of anonymity to share private conversations.

In conversations with donors and Trump advisers after the February event, Musk repeatedly raised the border and his fears that the 2024 election will not be secure. “The border and election integrity seem to be the two things he cares about,” said one person who has spoken to him.

Neither Trump nor any of his advisers were present at the event, which was convened by the billionaires.

Musk’s money is expected to build a campaign apparatus in a number of swing states amid widespread Republican concerns that Trump’s team does not have a sufficient program to get out the vote, people familiar with the plans said.

It’s a stark shift from 2016, when Musk told CNBC days before the election that he felt Trump was “not the right guy” because he “doesn’t seem to have the sort of character that reflects well on the United States.”

After winning the White House, Trump tried to woo Musk and other CEOs, meeting with them at Trump Tower in New York City in December 2016 and again shortly after his inauguration. Trump praised Musk throughout his presidency as a “friend,” “somebody I have great respect for,” and “one of our great brains.”

In 2020, Trump showed up to celebrate as SpaceX became the first private company to launch humans into space. And he supported Musk’s decision to defiantly reopen Tesla’s Fremont, Calif., plant after county officials ordered it shut down during the covid-19 lockdowns.

But Musk found Trump’s first term disappointing, according to two people familiar with his thinking. In 2017, Musk stepped down from two of Trump’s presidential advisory councils to protest Trump’s decision to pull out of the Paris climate agreement. “Climate change is real,” he tweeted. “Leaving Paris is not good for America or the world.”

During the 2020 election, Musk favored Biden.

A few months later, the White House invited every major American automaker except Tesla to a splashy event on the South Lawn. The electric vehicle summit included Ford, Stellantis and General Motors, along with the United Auto Workers. Tesla, the only nonunion American auto giant, petitioned to be included, but the Biden administration left the company out - a decision Musk later described as “the White House giving Tesla the cold shoulder.”

A former Biden administration official, speaking on the condition of anonymity to discuss internal conversations, said the White House kept the gathering small because covid-prevention measures were still in place. But the official said it’s also true that Biden, with the UAW in attendance, wanted to burnish his pro-labor reputation.

Musk took it as “the Biden administration was mean to me,” said the official, who attended the event. “Is this just because you guys don’t like Elon?” the official recalls a Tesla executive asking.

The snub was a miscalculation that later overtures to Tesla failed to overcome, the official said. In a Christmas Eve post on X, Musk listed the event and Biden’s comments crediting GM’s leadership with the EV revolution as among his complaints with the Biden administration.

Since the event, Biden has occasionally criticized Musk directly. He said Musk’s relationships abroad were “worthy of being looked at” after a reporter asked if Musk’s ownership of Twitter was a threat to national security.

And when Musk expressed pessimism about the economy, Biden shot back: “Lots of luck on his trip to the moon” - an apparent non sequitur. “Thanks, Mr. President!” Musk responded on X, reposting the press release that SpaceX was under contract with NASA to build a spacecraft to bring American astronauts back to the moon.

Last November, the Biden White House condemned Musk for what it called the “abhorrent promotion of antisemitic and racist hate” in his social media feed, contributing to an exodus of advertisers from X. Musk apologized.

Political differences

If Musk was disappointed by Trump’s White House, he soon grew frustrated by Biden’s, according to a person who has known Musk for years. Musk has been infuriated by Democrats on social issues, said the person, who spoke on the condition of anonymity to share private conversations, but was especially frustrated by the Biden administration’s approach to innovation and regulation.

During the covid-19 lockdowns, Musk frequently lashed out against prevention measures and expert opinions. He also found himself weighing in increasingly on social issues, embracing politics in a way he hadn’t during much of the Trump administration.

One executive who worked with Musk, speaking on the condition of anonymity to discuss his former boss, said Musk’s forays into the culture wars appeared to be driven by ideological conviction: “The battle wasn’t motivated by trying to make money.” Musk reinstated Trump’s Twitter account in 2022 - soon after he purchased the company - reversing a decision by previous management that Trump had glorified violence after the Jan. 6, 2021 attack on the U.S. Capitol.

This month, Musk announced that SpaceX would relocate its headquarters to Texas from California to protest a new California law that bars school districts from requiring that parents be notified if their child changes their gender identification.

Musk has a transgender daughter, Vivian Jenna Wilson, who disavowed her father in 2022. In an interview last week with conservative psychologist Jordan Peterson, Musk said Wilson had been “killed” by what he called the “woke mind virus.” (Wilson soon took to Threads to decry Musk’s descriptions of her childhood as “entirely fake.”)

During the interview, Musk also praised Trump, saying he had shown “instinctual courage” when he jumped up after being grazed by a bullet in an assassination attempt during a July 13 campaign rally in Butler, Pa.

“Now you have to admire that Trump, after getting shot, with blood streaming down his face … nonetheless was fist-bumping,” Musk said, and telling the crowd to “fight, fight.”

Musk tweeted his endorsement of Trump less than an hour after the shooting, touching off a wave of other Silicon Valley endorsements.

Brian Hughes, a senior adviser to the Trump campaign, said Musk’s endorsement is a sign of something bigger. “Many of the nation’s most important leaders in technology and innovation are concerned with the damage done to their industry by the Biden-Harris Administration’s failure to handle our economy and moves to overburden innovators with government bureaucracy and unrelenting regulation,” Hughes said in an email.

Last week, Vice President Harris’s campaign signaled that it would not bend over backward to try to win Musk back. “Arrogant billionaires only out for themselves are not what America wants or what America needs,” Harris campaign spokesman James Singer told The Washington Post when asked about Musk’s endorsement of Trump, echoing earlier comments.

So far, Musk has been dismissive of Harris. On Friday, he praised a video on X that was manipulated to make Harris appear to say she was a “deep-state puppet” who didn’t know anything about running the country. “This is amazing,” Musk commented.

After the election

While analysts and investors predicted a second Trump administration would be good for Musk, there are no guarantees with the former president.

In a move to court traditional manufacturers, Trump vowed at the Republican National Convention to “end the electric vehicle mandate on day one,” which he said would save the U.S. auto industry “from complete obliteration” and save consumers thousands of dollars.

Trump also has promised a fresh trade war with China, which would bring supply chain uncertainty for almost all major manufacturers, Tesla included.

And Trump has not always praised Musk: In a post on Truth Social in 2022, Trump bragged that Musk had sought his help on “subsidized projects,” including “driverless cars that crash, or rocket ships to nowhere,” adding that he could have required Musk to “drop to your knees and beg” and Musk would have done it.

Gene Munster, managing partner at Deepwater Asset Management, said Musk’s alliance with Trump is also likely to alienate many Tesla buyers. On Tesla’s earnings call last week, Musk seemed to acknowledge the risks of Trump 2.0, saying the potential loss of the Inflation Reduction Act “would hurt Tesla slightly.”

But Musk’s support for Trump is a “trade-off,” Munster said, that involves accepting short-term negatives for a bonanza of potential positives in the long term.

“Near-term, it’s going to be some form of a headwind. Trump can be polarizing,” Munster said. But “I think that Musk knows this. And ultimately he doesn’t care.”

Trisha Thadani, Cat Zakrzewski and Christian Davenport contributed to this report.