Trump National Westchester’s caddies are splitting a $25,000 bonus this week after partnering with President Donald Trump for the club’s annual caddies’ day, and Trump came away with the win. The victory lands just weeks after he claimed two division titles at his New Jersey course, keeping his golf record in the spotlight.

This tournament was a little different from the others he had played and won. This event brought the president together with the people who work for him on the course, pairing members with staff for 18 holes.

Page Six reported that Donald Trump won the event, but the actual scores remain undisclosed.

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Caddies’ day is the one event on the club calendar where staff play alongside members rather than working the bag, and the bonus turns Trump’s win into a payout for the people who carry his clubs the rest of the year, a detail that separates this title from his other club victories.

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Page Six reached out to the White House to confirm the win.

“Fact check: true. President Trump is a winner,” Olivia Wales, White House assistant press secretary, told Page Six about the win.

The 7,300-yard, par-72 course, designed by Jim Fazio, sits on land once home to Briarcliff Country Club and Briar Hall Country Club before Trump acquired the property in the 1990s and reopened it in 2002; its signature hole is a 101-foot waterfall at the par-3 13th.

Trump’s win follows his senior and super senior club championships at Trump National Golf Club Bedminster in New Jersey, where he posted a two-under 70 to take both divisions. According to Bedminster, he swept both in 2023, then took just the senior crown in 2024, before reclaiming both this year. He has yet to enter a Bedminster senior field and come away empty-handed since the championship returned to his calendar.

“I won with a score of 70, and am so honoured in that, unlike the rest of the field, I’m given very little time to practise, because I’m focused on many other things,” Trump wrote in a Truth Social post. “It’s called TALENT, and I have it, and they don’t!”

Trump owns numerous golf clubs and courses worldwide. A few days earlier, the Bedminster course where he won the two championships hosted LIV Golf New York, and he was attending.

Donald Trump meets Yasir Al-Rumayyan and golfers at LIV Golf New York

Trump was on site alongside PIF governor Yasir Al-Rumayyan and nine-time major winner Gary Player, whom he ranked among the top three golfers in history behind Tiger Woods and Jack Nicklaus. The same weekend, NORAD scrambled F-16 fighter jets after two aircraft breached restricted airspace over the property on August 9, escorting both out without injury or damage.

Two wins in three weeks, on two properties he owns, keep golf stitched into Trump’s public image, and with neither scorecard surfacing and major tour dates already booked across his portfolio, each new claim adds to a tally outsiders can track but never confirm.