Trump campaign 'may have crossed a legal line' by not naming winner in dozens of sweepstakes

For the bulk of former President Donald Trump's 2024 campaign, he's had multiple ongoing contests and sweepstakes to entice donors. But none of them have a publicly named winner, save for one.
The New York Times reported Thursday that the ex-president has hosted more than 40 such giveaways of merch and travel opportunities with a combined retail value of more than $180,000 dating back to early 2023, when Trump announced his 2024 candidacy. According to the paper, there has been at least one sweepstakes — and often several happening at once — for 446 of the 673 days he's been campaigning.
Currently, the only Trump supporter identified as a contest winner is William McGuffin, who won a trip for both himself and his son to meet Trump at the Miami Grand Prix. The Times was unable to verify with the campaign that there were any other winners of the 41 sweepstakes Trump's campaign has held to date after sending a request for names of winners and their contact information.
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The Times' report noted that most of the contests include paid airfare for a supporter and a guest to meet Trump and/or Sen. JD Vance (R-Ohio) in different locations, including his Mar-a-Lago estate, his Bedminster, New Jersey golf resort and various cities across the country. Other sweepstakes prizes offered signed merch like hats, footballs, a flag Trump hugged while he was at the Conservative Political Action Conference and podium signs, among others.
Because the Federal Election Commission regulates campaign sweepstakes, the Times' Karen Yourish and Lazaro Gamio reported that the former president "may have crossed a legal line" by not publicly naming winners of trips and signed items. They also wrote that Trump could be opening himself up to lawsuits from supporters or state and federal regulators for not abiding by sweepstakes rules.
“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,” advertising and marketing attorney Kyle-Beth Hilfer told the Times. “Any ambiguity could lead to a legal challenge from an entrant or even a regulator."
Vice President Kamala Harris' campaign, on the other hand, has abided by sweepstakes rules. Yourish and Gamio wrote that Harris' campaign identified six winners of nine sweepstakes, with the other three contests still ongoing. Participants in those events were offered a chance to meet President Joe Biden and former President Barack Obama, a trip to a star-studded fundraiser in Hollywood and various merch.
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Trump's third bid for the White House has been marked by a unique lack of transparency. Earlier this year, Juleanna Glover — a veteran lobbyist and former George W. Bush administration senior staffer — wrote an op-ed for the Times remarking on how little disclosure Trump has provided on how donor money was spent. She accused the former president of dumping donors' contributions "into a legal and financial black hole" that made it difficult to trace how billions of dollars Trump supporters donated to his multiple campaigns was spent.
"Anyone who has spent time reviewing Donald Trump's campaign spending reports would quickly conclude they're a governance nightmare," Glover wrote. "There is so little disclosure about what happened to the billions raised in 2020 and 2024 that donors, and maybe even the former president himself, can't possibly know how it was spent."
Click here to read the Times' report in full (subscription required).
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