As Trump Ponders V.P. Contenders, He Asks: Can They Help Me Raise Cash?

As former President Donald J. Trump sifts through potential running mates, he has peppered some advisers and associates with a direct question: Which Republican could best help him raise money for the rest of the presidential campaign?

That inquiry reflects the evolving calculations of Mr. Trump’s vice-presidential search — and how his scramble to keep up with President Biden’s colossal fund-raising totals may be weighing on his mind as he considers his options.

Mr. Trump’s selection process, which is still in its early stages, has largely revolved around conventional questions like who could step in as president if needed, political calculations including contenders’ position on abortion rights, and more Trumpian curiosities like whether a politician physically resembles his idea of a vice president.

But Mr. Trump has asked several people about the fund-raising prowess of possible running mates, according to three people with direct knowledge of the conversations, signaling a fresh angle in his search for a running mate.

The initial feedback has pointed him toward a handful of members of Congress with strong donor connections and at least one deep-pocketed governor. One long-shot possibility with a proven record of raising piles of cash — former Gov. Nikki Haley of South Carolina — was only recently a bitter presidential rival, and her name can spark outrage from Mr. Trump.

“Trump is going to want a team player, and this is going to be about adding value to the ticket,” said former Speaker Kevin McCarthy, who remains close with Mr. Trump and set records for Republican fund-raising. “It’s also going to be about someone who understands the job — who understands the Senate and the House — because he’s not going to want to waste one minute in office.”

This article is based on interviews with nearly a dozen Republican operatives and politicians who are familiar with Mr. Trump’s deliberations, some of whom have ties to the possible contenders and all of whom insisted on anonymity to discuss the private conversations.

In some cases, Mr. Trump is still getting to know potential contenders.

After a recent meeting at Mar-a-Lago with former Representative Tulsi Gabbard of Hawaii, a Democrat-turned-independent who has become popular among conservatives, he made clear to advisers that she should be on his list of options.

In other cases, Mr. Trump has fixated on the whimsical over the practical. He has asked several people about running with Robert F. Kennedy Jr., saying he is intrigued by the branding potential of a “Trump-Kennedy” ticket despite his recent attacks on Mr. Kennedy and the unlikelihood of such a scenario. Mr. Trump’s campaign team remains adamantly opposed to the idea, and Mr. Kennedy, who is already running for president as an independent, has said he would not consider such an offer.

It is also unclear among Mr. Trump’s advisers whether he ultimately intends to give considerable weight to a contender’s fund-raising ability, or whether his recent focus is a consequence of his overall concerns about cash. That fixation has permeated both his presidential bid and his costly legal defense in his four criminal cases — and further blurred the line between the two.

The former president relied on one of his political fund-raising vehicles, the Save America PAC, to pay for roughly $50 million in legal expenses last year. He has started replenishing that fund with help from the Republican National Committee, where recently installed Trump loyalists now control the purse strings.

Mr. Trump’s campaign team, meanwhile, has acknowledged that it expects to be outspent by Mr. Biden and the Democratic Party. Mr. Trump has responded with a furious pace of fund-raising, despite his typical prickliness at the idea of having to ask wealthy donors for cash.

“There is no shortage of immensely qualified people President Trump can choose from,” said Steven Cheung, a Trump campaign spokesman. “He’ll make his decision when he is ready and at the appropriate time.”

If fund-raising concerns further influence his vice-presidential search, that path could lead toward a pair of former Republican presidential primary opponents, Gov. Doug Burgum of North Dakota and Ms. Haley, and a coterie of members of Congress, including Representative Elise Stefanik of New York and Senators Marco Rubio of Florida, Tim Scott of South Carolina and J.D. Vance of Ohio.

Mr. Trump has signaled interest in all of them as potential running mates, except for Ms. Haley. To some people, he is said to have shown indifference when asked about Ms. Haley’s joining his ticket. To others, he has savaged her with brutal and personal criticisms.

Still, one of the truisms of Trump World is that no one is ever completely cast out unless they want to be left out. For her part, Ms. Haley said during the campaign that she would not serve as anybody’s No. 2.

But when it comes to supplementing Mr. Trump’s own fund-raising ability, Ms. Haley could prove a compelling choice. Ms. Haley’s presidential campaign and allied groups collected more than $146 million, according to Open Secrets, which tracks campaign fund-raising.

Of that total, $14.3 million came in small contributions collected mostly online — an impressive sum considering that her team needed to find email addresses and phone numbers for donors not already supporting Mr. Trump.

Mr. Burgum, for his part, did not raise much for his presidential campaign, but he is worth hundreds of millions of dollars due largely to the sale of his computer program business to Microsoft in 2001.

Mr. Trump also has a history of populating his inner circle with wealthy businessmen. Mr. Burgum attended a fund-raiser at Mar-a-Lago this month and, at Mr. Trump’s request, addressed the crowd of about 100 donors, as did Mr. Scott and Vivek Ramaswamy, a businessman who ran for president this year, The Wall Street Journal reported.

Mr. Rubio built a formidable fund-raising operation for his own presidential bid in 2016. And while many of those donors, such as Isaac Perlmutter, the former chairman of Marvel Entertainment, are already supportive of Mr. Trump, others are not.

Norman Braman, a billionaire South Florida auto dealer, and Paul Singer, the founder of the Elliott Management hedge fund, two key financial backers of Mr. Rubio in 2016, both put money behind presidential primary opponents of Mr. Trump this year. Mr. Braman supported Gov. Ron DeSantis of Florida, and Mr. Singer donated to Ms. Haley.

One complication for Mr. Rubio’s vice-presidential prospects is that he and Mr. Trump are both residents of the same state, which could run afoul of a constitutional rule.

While Mr. Trump maintains additional homes in New Jersey and New York, and switched his residency as president, he has told people Mr. Rubio would have to legally move to another state to join the ticket.

Mr. Trump has told these people that it would probably be difficult for Mr. Rubio to move his family but that Florida voters would be too upset to lose the former president as a resident.

Mr. Scott, the only Black Republican in the Senate, has already started helping Mr. Trump raise money.

Ahead of a Trump fund-raiser at Mar-a-Lago this month, he called several donors to urge them to pitch in. He was also one of the hosts of a fund-raiser in Greenville, S.C., held days before the state’s presidential primary, that netted a reported $6 million for the former president.

As Mr. Scott ran for president last year, donors plowed $45.9 million into his campaign and allied groups, about two-thirds of which came from large donations, according to Open Secrets.

Larry Ellison, a co-founder of Oracle and a longtime Scott supporter, has lobbied Mr. Trump to add the South Carolina senator to his ticket. Mr. Ellison’s involvement was first reported by Puck, which has also described Mr. Trump’s interest in contenders who are strong fund-raisers.

Ms. Stefanik’s network of donors comes from across the conservative spectrum.

A former aide in President George W. Bush’s White House, Ms. Stefanik has received support since her first House victory a decade ago from several wealthy establishment donors, including Cliff Asness, a billionaire founder of AQR Capital Management, who backed Ms. Haley’s presidential bid, and Mr. Singer. She met with recently with Mr. Singer and laid out why she thought Mr. Trump would win in November, and Mr. Asness hosted a small group meeting for her at his office where she did the same.

Since vigorously defending Mr. Trump against his first impeachment in 2019, Ms. Stefanik has also developed relationships with donors affiliated more closely with his conservative movement. Mr. Perlmutter has hosted fund-raisers for her along with Steve Wynn, the casino mogul, who has privately urged Mr. Trump to consider Ms. Stefanik.

Ms. Stefanik, who replaced former Representative Liz Cheney as the chairwoman of the House Republican Conference, has also drawn interest more recently from donors compelled by her push to investigate antisemitism on college campuses. In the first three months of the year, she collected $7.1 million for her own re-election and other Republican causes, her campaign announced this month.

Mr. Vance is close with Donald Trump Jr., the former president’s eldest son and a key political adviser, and the pair helped raise money to pay for a Trump rally in Ohio to benefit Bernie Moreno, the Republican nominee for Senate in the state.

Mr. Vance also has ties to Silicon Valley from his time working as a venture capitalist in San Francisco for Peter Thiel, the billionaire founder of PayPal. Mr. Thiel was one of Mr. Trump’s biggest donors in 2016 and spent roughly $35 million on Republicans in 2022 but has said he does not plan to be involved in the presidential contest this year.

One of Mr. Thiel’s close associates, David Sacks, gave more than $1 million to political causes in 2022. He was involved with the announcement of Mr. DeSantis’s primary challenge against Mr. Trump but was also spotted at a fund-raiser Mr. Vance held his year for Mr. Moreno, where Mr. Sacks spent time chatting with the younger Mr. Trump.

Mr. Vance and Blake Masters, an Arizona House candidate and fellow Thiel acolyte, are exploring a Silicon Valley fund-raiser for the elder Mr. Trump, although a person familiar with the matter said the event was still in the planning stages.