Kai Trump, the eldest daughter of Donald Trump Jr. and Vanessa Haydon – and the oldest grandchild of former President Trump – was just 14 when she made her Instagram debut.
Her very first post? A photo with her grandfather and Tiger Woods, taken on a sunny day at one of Trump’s golf courses and shared on February 23, 2021.
‘Wishing Tiger luck and a speedy recovery. Also wishing his family all the best in these incredibly trying times. Get well soon! #goat #tigerwoods,’ she captioned the shot, referencing Woods’ serious car crash in early 2021.
Now four years later, people have been noticing the significance of the post after Kai’s mother started dating the golfing legend.
Vanessa and Trump Jr divorced in 2018 after 12 years of marriage and since Thanksgiving 2024 Vanessa has been dating Woods.
Sharp-eyed fans have been commenting on Kai’s first post with one writing: ‘Ironic this is her first post when he’s now dating her mom.’
Now 18, Kai has made a name for herself in golf. A senior at The Benjamin School in North Palm Beach, Florida, she committed to the University of Miami last year and is poised to become a star in one of the country’s top golf programs.
She’s also one of the most-followed student-athletes online, with a growing fanbase thanks to her YouTube channel and golf content.
Last fall, she played against popular golf creator Garrett Clark and regularly shares behind-the-scenes vlogs.
Her popularity has paid off. She recently landed a major NIL deal with Accelerator Active Energy, joining stars like Livvy Dunne and Travis Kelce.
Her announcement video – complete with a mock presidential speech – showcased her signature humor: ‘My fellow Americans and content creators. After months of reflection, I made a decision. I’ll be running – no, stepping – into a new role.
‘One with great responsibilities and 100 per cent natural caffeine. I’ve partnered with Accelerator!’
Speaking to Fox, Kai said the ‘organic’ partnership was a natural fit: ‘I love energy drinks… I don’t eat a lot of sugar, because I get a little jittery and I crash and with accelerator there is no sugar and I don’t crash at all.’
She reportedly holds a $1.2 million NIL valuation and is now part of a brand lineup that includes Dunne – who launched her own cotton candy flavor in April – and Super Bowl champ Kelce.
Kai is the eldest of Don Jr. and Vanessa’s five children. Her younger siblings include Donny, 16, Tristan, 13, Spencer, 12, and Chloe, the youngest.
Kai has previously spoken about how her grandfather has pushed her to be a better golfer.
‘He taught me to just keep on working at it, and, honestly, I’ve gotten a lot better in past years with golf, but, he really just [taught me to keep] trying to keep on fighting and keep on practicing and whatnot,’ she told ‘Fox & Friends’ last month.
‘And I love playing golf… it’s something that we share, a special bond together.’
The high school student also spoke about the difficulties in having such famous relatives.
‘I mean, it’s a lot to handle sometimes with the public eye and also being a high school student and just like a normal kid,’ she said.
‘But honestly I wouldn’t trade it for anything. I’m very lucky and grateful for the opportunity I have to meet all these people and meet world leaders.
‘I’m very thankful and just lucky to have this opportunity.’
