They helped Trump take back the White House. The rewards have come swiftly.

CNN
 — 

David Bailey, a longtime Bitcoin investor and evangelist, had tempered expectations in early 2024 when he first pitched Donald Trump’s campaign on the political upside of embracing cryptocurrency. Even after Trump pledged over the summer to make the US a Bitcoin haven and the industry spent tens of millions of dollars supporting his presidential bid, Bailey suspected Trump’s overture might be a fleeting appeal for crypto voters rather than a lasting commitment.

Yet since returning to office, Trump has upended the federal government’s wary stance toward cryptocurrency just as he said he would. Earlier this month, he signed an executive order directing the Federal Reserve to hold Bitcoin alongside gold—a move long sought by crypto advocates and once considered improbable.

“If a year ago you put me into hypnosis and said, ‘Describe to me your deepest dreams of what could happen,’ this would be straight-up fantasy,” said Bailey, who owns the Bitcoin conference where Trump first stepped out as a pro-crypto candidate. “I never would have believed it could happen.”

Trump’s return to power was achieved in part through an unorthodox coalition-building strategy. He courted groups who might’ve been overlooked by Republican candidates, like Bitcoin enthusiasts, making direct appeals with policy promises tailored to specific audiences.

For those who played along, the rewards have come swiftly.

The Lumbee Tribe in North Carolina, for instance, had reliably voted Democratic in presidential elections for decades. But an eight-year pursuit by Trump for the battleground state’s predominant native group – culminating with his promise last fall to grant the tribe much-coveted federal recognition – appeared to resonate at the ballot box. In Lumbee-rich Robeson County, where Barack Obama twice won handily, Trump secured a 28-point victory, his largest margin across three races.

Three days after taking office, Trump signed a memorandum declaring it US policy “to support the full federal recognition” of the Lumbee Tribe, the strongest statement to date from the Oval Office.

Transactional? Perhaps, but that’s politics, said Lumbee Tribe Chairman John Lowery, who told CNN, “It feels good to be courted.”

“Everyone is in their lane and they’re not going to get out of it. You’re either hardcore this or that,” Lowery said. “We are hardcore for those who are showing the effort and putting in the work to get our vote. And we have a tendency to reward that more than any ideological view. There’s something about good old retail politics. Trump has done that on this issue.”

Trump’s unconventional approach extended to union workers, a longtime Democratic stronghold. Amid the outreach, and with many of his members increasingly leaning toward Trump, Teamsters President Sean O’Brien stunned Democrats by delivering a primetime address at the Republican National Convention (getting a lukewarm response from the GOP audience). Later, the union withheld an endorsement in the presidential race for the first time in decades, a considerable blow to the Democratic ticket.

The strategy paid off for Trump: He won 45 percent of the vote from union households, according to a CNN exit poll, a striking watermark for a GOP candidate.

For O’Brien, the calculated risk proved worthwhile during a Nov. 21 visit to Mar-a-Lago, where he advocated for Lori Chavez-DeRemer, then a Republican lawmaker from Oregon, to lead the Department of Labor. After three hours of intense discussions, Trump agreed to nominate Chavez-DeRemer and, most critically, vowed not to relent in face of expected pushback from business groups who saw her as too sympathetic to unions, O’Brien told CNN. The next day, his transition team announced Chavez-DeRemer as his pick for Secretary of Labor and she was confirmed earlier this month.

The episode solidified the Teamsters as “one of the most influential unions in the country,” O’Brien said.

“We know we got criticized by our peers in organized labor, but we’ve watched our organization do the same thing every single campaign and expect a different result,” he said. “We didn’t want to take that approach.”

Trump’s early efforts to appease key constituencies comes as his political operation is already plotting how to motivate his unconventional coalition to show up for Republicans in next year’s midterm elections. While some in Trump’s movement have predicted a more permanent political realignment is in the offing, the White House remains concerned that the president’s appeal to certain groups may not translate to GOP congressional candidates.

It’s unclear, for example, whether Libertarian voters and supporters of ex-presidential candidate Robert F. Kennedy Jr. can be convinced Trump needs to keep Republican majorities in Congress, a White House official told CNN. Trump appealed to both groups during the campaign – a calculation his political team made early after watching the Libertarian candidate siphon votes from him in 2020.

Trump’s effort to court Libertarians last summer—including a speech at their national convention where he endured boos before promising to pardon Ross Ulbricht, the imprisoned founder of an illicit online market called Silk Road—seems to have worked. The Libertarian ticket garnered its smallest share of the vote since 2008. A day after taking office, Trump fulfilled his pledge to pardon Ulbricht.

Similarly, Trump named Kennedy Secretary of Health and Human Services shortly after the election after vowing the prominent vaccine skeptic would have a role overseeing health issues in his administration.

Angela McArdle, the Libertarian Party chair at the time, has publicly insisted giving Trump a platform at the convention has paid off for her members.

“Don’t expect perfection,” she posted on X this week. “Take the wins!”

But not everyone is pleased with the arrangement. Steven Nekhaila, the current party chairman, called Ulbricht’s clemency a “good transaction from the libertarian movement,” but added that Libertarians were naive if they thought Trump wanted “anything more than our vote.”

“It’s even more naive to think we won’t be discarded when we’re no longer convenient the same way Rep. Thomas Massie was cast aside when he was no longer in line,” Nekhaila said, referring to Trump’s threat to primary the conservative Kentucky congressman after he defied the president on a vote to fund the government.

Trump’s early actions on cryptocurrency have also drawn some criticism, including from supporters within the industry who have balked at his growing financial interests in digital assets. Once a vocal opponent of Bitcoin, Trump’s change in tune last year came as his family launched a crypto venture spearheaded by his sons. Days before his inauguration, Trump also announced a new meme coin capitalizing on his name, presenting new conflicts for a president who already has more than any modern predecessor.

When Trump unveiled his family’s new digital asset business, Nic Carter, a crypto investor who supported the Republican, said, “At best it’s an unnecessary distraction, at worst it’s a huge embarrassment and source of (additional) legal trouble.”

Bailey, speaking to CNN en route to a dinner at the White House for donors, dismissed the conflicts as examples of Trump’s “entrepreneurial spirit.” Regardless, Bailey believes the former president has forced the political class to take the cryptocurrency community seriously.

“Our voter bloc is big and growing quickly,” he said. “And it will be up to the parties to speak with us.”

While Trump’s early actions have earned plaudits from the groups his campaign targeted, their leaders also suggest there’s more to be done to fully satisfy his commitments to them. Trump has yet to say, for example, how much Bitcoin the Federal Reserve should stockpile. The Teamsters is closely watching how labor fares in early decisions under Trump by the National Labor Relations Board and whether his administration stands by union provisions in existing federal contracts.

The Lumbee Tribe still needs an act of Congress to access the federal benefits granted to other federally recognized American Natives. Lowery said he is “cautiously optimistic” Trump can champion a legislative push, but if Republicans with full control of government can’t get it to his desk, Lumbee voters may swing back toward Democrats.

“You’ve got to remember us,” Lowery said, “and you can’t take us for granted.”