The Contests, Clubs and Big Promises of Trump’s Fund-Raising Emails

Since former President Donald J. Trump announced his 2024 candidacy, his campaign has promoted dozens of contests for supporters to win signed merchandise or “V.I.P.” trips to meet Mr. Trump. It has offered adherents myriad “exclusive” opportunities to join clubs to give counsel to Mr. Trump, and it has repeatedly claimed that Mr. Trump is personally reviewing lists of small donors.

But most of the contests seem to have no winners, and the campaign did not confirm or provide evidence that the club members have had any opportunity to advise the former president or that Mr. Trump is paying any attention to small donor rosters.

The New York Times looked at some 7,400 emails sent by the Trump campaign since Mr. Trump entered the presidential race. About one-third of the messages dangled an incentive to entice recipients to make a small donation.

The Times also reviewed campaign emails from the Democratic candidate and former candidate: Vice President Kamala Harris and President Biden. Combined, they have sent just over 1,600 emails since Mr. Biden declared his candidacy in April 2023.

Ms. Harris, and before her Mr. Biden, have far outpaced Mr. Trump in fund-raising this cycle, including from small-dollar donors. About $454 million in donations under $200 has come into the Biden and Harris campaigns, more than double what the Trump campaign has made.

While one-quarter of the Biden-Harris messages offered donation incentives, there were far fewer options: nine contests, two memberships, chances to be listed on a wall of donors at Mr. Biden’s former campaign’s headquarters in Delaware, and about three dozen unique pieces of merchandise from the official campaign store.

Whether they are written by Mr. Trump himself or by members of his staff, as is likely the case, the tone of the emails is generally consistent with Mr. Trump’s manner in public appearances and on social media: both chummy and alarmist.

To be sure, emails using sensationalistic language, and even manipulative tactics, are not unique to the Trump campaign. A study published in the journal Big Data & Society of thousands of political emails sent during the 2020 election cycle found that — in order to nudge recipients to open emails — campaigns frequently use subject lines that include clickbait or give the impression that a message is a continuation of an ongoing conversation. The Trump campaign has used these techniques, sending emails about joining its “Deadline Donor List” with subject lines like “Alert: (1) New Message – Action Required” and “Confirm Payment Information.”

Mr. Trump’s campaign team may not be alone in some elements of its email strategy. But both in sheer number (about 75 emails per week, on average, throughout this campaign cycle) and in syntax, the former president’s campaign emails stand out. They swing wildly between doomsday tirades and deeply affectionate language — then, often, dangle a sweetener to donate.

A missive sent in May, for instance, ticked through a short list of Mr. Trump’s current grievances: “the ILLEGAL RAID on my beautiful Mar-a-Lago,” “the RIGGED BIDEN TRIALS forcing me off the campaign trail,” and “the RUTHLESS ATTEMPTS TO SILENCE MAGA & DESTROY AMERICA.”

But that was not all that was on Mr. Trump’s mind. “You are the reason I wake up every morning. I love you to the moon and back, and I really mean that,” he wrote. “So before the day is over, I want to see your name as a member of the first ever TRUMP DIAMOND CLUB.”

Enter to Win (Maybe)!

Sweepstakes are a near-constant fixture of Mr. Trump’s campaign email corpus. In the 673 days of Mr. Trump’s current candidacy covered by The Times’s analysis, his campaign ran at least one active contest — and sometimes several simultaneously — for 446 of them.

Most of the Trump campaign’s contests have promised once-in-a-lifetime experiences: V.I.P. trips to Mr. Trump’s private resorts, campaign rallies and fund-raising receptions. Contest prizes have included round-trip airfare, hotel accommodations, and a photo with Mr. Trump for the winner and a guest, with approximate retail values running up to $24,000.

A smaller handful of sweepstakes have offered memorabilia like signed MAGA hats, autographed footballs and even the American flag displayed on stage during Mr. Trump’s speech at the 2024 Conservative Political Action Conference.

In all, the combined approximate retail value of the contest prizes offered by the Trump campaign since Mr. Trump announced his candidacy totals more than $180,000.

The Times could not verify that a vast majority of that value has made its way to Mr. Trump’s supporters. Similar questions have arisen about contests Mr. Trump’s campaign and political action committee have run in years past.

The Times sent the campaign a detailed list of every contest it had promoted in fund-raising emails from Nov. 15, 2022, to Sept. 16, 2024, and asked the campaign to confirm that each contest had a winner and to provide the names of the winners. The Times also asked the campaign to provide photos of the winners with Mr. Trump in cases in which a photo was part of the prize, and a link to a “personalized” Christmas message from Mr. Trump offered as a prize in December 2022.

The campaign did not confirm that each contest had a winner. It also did not provide winners’ names, photos or a link to the Christmas video.

In several emails to subscribers since late August, the campaign has included two photos it said were of contest winners: a man named William McGuffin and his son, as well as another pair whose names the campaign did not provide. A Times review of local news and social media sources did not find winners for any of the other 39 contests.

The campaign provided two statements: one by Mr. McGuffin and one by a campaign adviser. Mr. McGuffin said that he and his son went to their “first and only political rally” on May 1, and then received a call on May 3 saying he had won a trip to Formula One’s Miami Grand Prix for a “private meet and greet” with Mr. Trump. Mr. McGuffin confirmed in a phone call with The Times that he and his son had met Mr. Trump.

In addition to asking the campaign about contest winners, The Times reviewed local news and social media posts for evidence of winners beyond Mr. McGuffin and did not find any additional winners. It remains possible that each of these more than 40 contests had a winner. But if they did not, the Trump campaign may have crossed a legal line.

Contests like the ones both campaigns have run are legally considered sweepstakes, which are a regulated category. Federal Election Commission regulations allow political committees to run sweepstakes, but do not specify the rules under which they are run. In the absence of such rules, sweepstakes regulations from federal and state regulators should apply, according to campaign legal experts.

“Sweepstakes rules should be crystal clear about whether a sponsor will award all prizes or whether a sponsor will choose alternate winners if the original potential winners are disqualified,” Kyle-Beth Hilfer, an advertising and marketing law attorney in New York, said in an email. “Any ambiguity could lead to a legal challenge from an entrant or even a regulator.”

The Harris campaign provided The Times with the names of winners for six of its nine contests. The remaining three are still ongoing or the campaign is working out timing with the winners, it said.

Exclusive Promises of Access

Supporters who sign up for Trump campaign emails can feel like they are just a click away from being in Mr. Trump’s inner circle.

An email sent soon after Mr. Trump announced his candidacy, and signed “Trump Fundraising Director,” dialed up the urgency — and the personal appeal, suggesting Mr. Trump had repeatedly asked about the email’s recipient. “We are all counting on you,” it said. “We expect to hear from him any minute, so you MUST HURRY. We know he is going to ask about you. AGAIN.”

“I am honored to invite you to become an Official Trump Campaign Cabinet Member,” the former president wrote in dozens of emails from Dec. 9, 2022, to Jan. 24, 2023. “I am only inviting a very small and select group of Patriots to join me.”

The so-called Cabinet would provide Trump and his team with “valuable insight and advice as we make some of the most important decisions leading up to the 2024 Presidential Election and BEYOND,” he added.

“Do you need a job?” Mr. Trump asked in the subject line of an offer to join his “Official Advisory Board.”

“I’m opening up a few spots on my team, and one of them is reserved just for you,” Mr. Trump said.

The Times counted at least 19 different memberships, as well as dozens of promises that Mr. Trump would review names on donor lists — promises meant to encourage email recipients to donate.

The campaign did not respond to questions about the mechanisms by which any members of these groups provide advice to Mr. Trump, whether the members have ever met in person or virtually (with or without Mr. Trump), how Mr. Trump “personally” selects the people invited to join and how many people have joined. It also did not confirm or provide evidence that Mr. Trump is personally reviewing lists of small donors.

The campaign has also promised to make at least one donor list tangible in a way that must surely be a first in presidential campaign history: Emails sent from June 12 to July 11 offered donors the chance to have their names engraved onto the tail of “Trump Force Two,” the private plane Mr. Trump reserved for his running mate’s use. Dozens had been added by late July.

Platinum Cards and Christmas Sweaters

Emails from Mr. Trump have also offered more than 100 physical items as donation incentives. The campaign has furnished the hats, shirts and mugs that have long been campaign-finance mainstays — but with an unmistakable Trumpian twist. (The MAGA hat alone has proved a canvas for abundant variation; at least 30 different colors and styles have been offered.)

The campaign has also ventured into new corners of the branded-merch universe.

The American Express Black Card, for instance, is famously available by invitation only — but the Trump Black Card can grace the wallet of any donor willing to part with $75 per month to join the “Trump Elite Membership Program.” The Black Card is among at least five physical membership cards the campaign has offered; others include platinum and gold varieties, plus “Campaign Membership” and “Trump Freedom” options.

Mr. Trump’s emails have also offered a “Personalized Trump 2024 Doormat,” an “Official Trump MAGA Cooler,” “Exclusive Trump Christmas Stockings,” “Official Trump Golf Balls” and more.

The campaign quickly churns out new items of merchandise after Mr. Trump makes news. An “I Stand with President Trump” T-shirt was available within a day of Mr. Trump being indicted by a grand jury for falsifying business records related to the reimbursement of hush money paid to cover up a sex scandal.

Email offers for T-shirts and mugs with Mr. Trump’s mug shot and the words “NEVER SURRENDER!” appeared shortly after Mr. Trump was booked on charges that he attempted to overturn the 2020 presidential election.

By December 2023, supporters could receive “Limited-Edition Mugshot Christmas Sweaters for FREE!” (with a campaign contribution of $50 or more).

More recently, Mr. Biden’s decision to drop out of the race and Ms. Harris’s ascension to the Democratic nomination has rendered moot some of Mr. Trump’s merchandise offerings. A number of items had been produced earlier in the race specifically to poke fun at Mr. Biden, including “Evict Biden” and “Crooked Joe” T-shirts and “Let’s Go Brandon” gift-wrapping paper, a reference to a meme involving an expletive and the president’s name.

Although the Trump campaign’s emails have frequently referred in negative, even pejorative, terms to Ms. Harris since she became the nominee, they have not yet offered any merchandise specifically poking fun at her.

From Sentimental to Surreptitious

In response to questions from The Times about the offers the Trump campaign includes in its emails, the campaign responded with a statement from a senior adviser, Brian Hughes. “President Trump and our campaign have a strong and effective fund-raising operation that includes digital platforms,” he wrote. “President Trump’s movement to save our nation inspires hardworking men and women from all over America to play a financial role in our campaign and MAGA movement.”

To encourage those donations, Mr. Trump’s email strategy alternates between scaremongering and statements of devotion to the reader that are sometimes startlingly personal, including frequent declarations of love.

At times, it has even appeared to include reverse psychology. Mr. Trump’s emails depend so heavily on a perception of intimacy that he sometimes asks his supporters not to spread the word — a highly unusual move for a political candidate.

“Please do NOT share this email,” Mr. Trump warned in an offer to accept an “EXTREMELY RARE” invitation for “PRIORITY ACCESS TO BECOME A 2023 ULTRA MAGA MEMBER” before it supposedly expired at midnight.

The campaign sent the same offer at least nine more times over the following two weeks.