“Luxury Homes, a Billionaire Boyfriend, and Stunning Outfits: Why Trump-Favorite Sydney Sweeney Shakes Off Critics” – Alison Boshoff

“Luxury Homes, a Billionaire Boyfriend, and Stunning Outfits: Why Trump-Favorite Sydney Sweeney Shakes Off Critics” – Alison Boshoff

Fifteen years ago, Sydney Sweeney, aged 13, and her family moved to Hollywood to allow her to follow her dream of making it as an actress. Money was tight – so tight that for eight and a half months she, her younger brother Trent and parents Steven and Lisa all lived in a single room in the Holiday Inn motel in Burbank, north-west Los Angeles. They simply couldn’t afford to rent anywhere else.

Bankruptcy beckoned, followed soon after by the breakdown of her parents’ marriage, due in part to those financial pressures.

Of their motel existence, she later said that that room ‘felt like my entire life… We were sharing a one-bedroom hotel room, no kitchen, no balcony’.

Success came slowly. Seven years after they moved, in 2017, she won a role in The Handmaid’s Tale. This was followed by her breakout performance in the teen drama Euphoria, which was broadcast two years later.

Then came The White Lotus and the romcom Anyone But You, which saw her chemistry with co-star Glen Powell become a global talking point. Extraordinarily, she said even at this point in her career she still didn’t have enough money to make ends meet.

Now aged 28, she’s said to be worth £37.7 million, travels by private jet, and has endless lucrative endorsements and film roles – and even, just possibly, an awards nomination in the offing for her truly powerful performance in the boxing drama Christy.

Indeed, she is closing the year as a young woman with such wealth that she has no fewer than three multi-million dollar homes in her property portfolio, including the £10 million oceanside mansion in the Florida Keys where she’s celebrating Thanksgiving.

And she’s even considering treating herself to a fourth.

Sydney Sweeney, now said to be worth £37.7million, experienced financial hardship during her childhood as her family gave everything to support her Hollywood dream

Sydney Sweeney, now said to be worth £37.7million, experienced financial hardship during her childhood as her family gave everything to support her Hollywood dream

Sweeney, one of the most desirable women in Hollywood, has, I¿m told, also struck the romantic jackpot with her new boyfriend, the music mogul Scooter Braun, writes Alison Boshoff

Sweeney, one of the most desirable women in Hollywood, has, I’m told, also struck the romantic jackpot with her new boyfriend, the music mogul Scooter Braun, writes Alison Boshoff

Could things get any sweeter for Sweeney who, against all the odds, has turned her life into such an extraordinary triumph?

Evidence of that triumph is all over her palatial home in glorious Summerland Key.

It has six bedrooms, a gargantuan kitchen with a custom walnut bar, cream marble flooring and a wine room with space for 520 bottles. One decorative touch is a 330 gallon aquarium, while the floor space comprises 8,000 square feet.

The outdoor space is a far cry from her balcony-less spell in the Holiday Inn, too, with an enormous curving pool on two levels looking out to the ocean, an outdoor kitchen, a boat ramp and more.

Her happiness extends not merely to her professional life, however. Sweeney, one of the most desirable women in Hollywood, has, I’m told, also struck the romantic jackpot with her new boyfriend, the music mogul Scooter Braun.

He is currently holidaying with her – along with her friends and her mother, from whom Sweeney has inherited her curvaceous figure – and they’ve been pictured messing around on jet skis, cuddling in the pool and sunbathing.

Sydney posted a video of herself waterskiing on Instagram on Thursday, showing off enviable confidence and skill.

Her home in the Keys was purchased a little over a year ago, and locals are getting used to seeing the actress around.

The palatial home of Summerland Key has six bedrooms, a kitchen with a custom walnut bar, cream marble flooring and a wine room with space for 520 bottles

The palatial home of Summerland Key has six bedrooms, a kitchen with a custom walnut bar, cream marble flooring and a wine room with space for 520 bottles

Sydney was pictured jet-skiing with Scooter this week near her home in Florida

Sydney was pictured jet-skiing with Scooter this week near her home in Florida

One resident of Summerland Key says: ‘She spends a lot of time in Big Pine Key. I know she’s been to the Winn-Dixie [supermarket] there to do her shopping quite a lot.’ A server at the nearby No Name Pub says that she may have been in ‘but we see a lot of famous faces and like to give them their privacy’.

Privacy is something that is in fairly short supply in Sweeney’s world – she’s been photographed everywhere from exiting the gym to kissing Braun passionately in New York’s Central Park.

Braun, who has managed Ariana Grande and Justin Bieber, can of course give his girlfriend pointers on how to cope with her fame. This professional success is rumoured to have awarded him a fortune of around $1 billion.

Now 44, Braun is said to be offering his girlfriend of five months professional advice if and when she wants it. Indeed, as a hardened showbiz veteran, he has more than walked through the fire.

For example, he and Bieber went their separate ways after 15 years as manager and client in 2023 – and this year it was reported the singer had agreed to pay him £24 million for cancelled shows and commission.

He’s also had issues with superstar Taylor Swift, when he bought the rights to her old songs after acquiring her former record label in 2019 for £226 million.

Swift claimed to be blindsided by this and accused Braun of ‘incessant, manipulative bullying’, before buying her songs back in May this year in a deal reportedly worth £271 million.

He is, it’s fair to say, loathed by ‘Swifties’ everywhere.

Sydney has come under criticism in Hollywood for being a registered Republican voter

Sydney has come under criticism in Hollywood for being a registered Republican voter

Braun met Sweeney in June at the luxurious and highly public Venice wedding of Jeff Bezos and Lauren Sanchez.

I’m told that, unlike bachelors such as actor Orlando Bloom and American footballer Tom Brady, Braun didn’t ‘hit on’ Sweeney.

However, they did chat and exchange numbers. A date followed when both were back in Los Angeles – which was ‘a nice surprise’ for Sweeney.

As soon as early October, I was being told by sources that this was a serious romance rather than a passing fling.

Braun treats her and her family with the utmost respect, and she finds his kindness and stability appealing. One source said: ‘Sydney’s friends and family are incredibly happy that she is with someone stable who treats her with complete respect.

‘With so many users in her life, her inner circle is relieved Scooter doesn’t need anything from her, not money or fame which has been a big issue for her previous relationships.

‘They can already see how much he takes care of her.’

Indeed, he has a vast £49 million mansion in Brentwood, Los Angeles, and his ex wife Yael is based in Montecito with their three children.

His girlfriend, however, is perhaps starting to catch him up in the property stakes.

Her charming Tudor-style house in Westwood, Los Angeles, was her first property purchase in 2021.

That hillside house cost £3.2 million and is accessed by a steep staircase or a tiny funicular railway which runs from the garage at street level.

Two years later, as her fame grew, she snapped up a £4.6 million house in Bel Air at auction along with her then fiance, the businessman Jonathan Davino. They were in the process of gutting and completely redoing it when they split up this April, and she has never spent a night there. It’s thought once building work is complete, it will be sold.

In October she toured a further property in Los Angeles – a ‘magical’ Bel Air estate, which is on the market for the first time in 80 years.

The asking price is £11.2 million and gossips say she ‘swooned’ over the house, which was built in 1936.

‘She likes old houses – buying and restoring them,’ a source said. It’s an expensive hobby.

The nine-bedroom house overlooks the Bel Air Country Club golf course, and, according to the estate agent, over the years guests have included Joan Collins, Joan Crawford and French singer Edith Piaf. There is a guest house for staff or security and a pool – of course – as well as a championship quality tennis court and a long private gated driveway.

This one, then, might just count as a forever home for Sweeney, who was raised in ordinary circumstances in Spokane in Washington State.

A sporty girl, she adored hiking, swimming and playing golf, as well as skiing, dirt biking and football. Her interests also extended to the academic, too – she was in her high school robotics team and maths club. She now reflects that she was trying to compensate for – or distract from – her remarkable physique.

‘I had boobs before other girls and I felt ostracised for it,’ she has said. ‘I was embarrassed and I never wanted to change in the locker room. I think I put on this weird persona because of my body.

‘So I did play every sport and I studied really hard and I did everything that people wouldn’t think I would do, to show them that my body doesn’t define who I am.’ After getting bitten by the acting bug aged 11, she presented her parents with a five-year career plan in the form of a spreadsheet which showed how she intended to make it in Hollywood. For years, they would devotedly drive her to auditions.

Aged 13, they took the plunge and moved to LA so she could try to make a go of it. Clearly, as the motel stay proved, this was a difficult period for the family.

She recalled: ‘I hated going home and friends or family members being like, “When are you going to come home and get a real job?” There were a lot of really condescending statements that would make me disappointed in myself and guilty that my parents had given up so much to allow me to follow my dreams.’

She added: ‘I always thought that when I turned 18, I’d have all this money and I’d buy back my parents’ house and put them all back together again. And I never was able to, and I never did.’ This was an impossibility because, by that point, her parents had separated.

Her mother, a former attorney, has moved back to Spokane, and Sweeney recently said she had paid off the mortgage on her home, a lakeside property in the family for five generations.

Her father, who works in hospitality, lives ‘off grid’ in Mexico.

‘My parents sacrificed so much to support my dream, and they lost so much during it. I just felt a responsibility to show them that it was worth it,’ she says.

Undoubtedly, her global fame has grown exponentially in 2025 – and she ends the year as someone who is both a sex symbol and a talisman in the culture wars.

Even in the Kardashian era of undressed dressing, she has pulled off one jaw-dropping look after another, with arguably the most impactful being the silver crystal mesh Christian Cowan dress she wore to the Variety Power of Women event last month.

The steel boned corset gave her a tiny waist and fixed all attention on her ample, all-natural bosom. (You can see why her grandmother reacted – according to Sweeney – to watching her love scenes in Euphoria by crowing: ‘Best t*ts in Hollywood!’)

Meanwhile her ‘great genes’ campaign for American Eagle denim this summer saw her simultaneously vilified by many – and praised by none other than Donald Trump.

Actress Aimee Lou Wood and actor Dan Stevens are among those who have lined up to denounce what they feel is the use of the language of white supremacy in the advert.

Sweeney has just shrugged that she likes to wear jeans and has ‘nothing’ to say on the subject. ‘You just know who you are,’ she has said.

‘And the people who matter and are your friends and your family, they know who I am.’

Another subject on which she has also remained silent is her status as a registered Republican voter – something that makes her an outlier in liberal Hollywood. Her Euphoria co-star Zendaya is apparently shunning her on the set of season three because of it – claims that the Dune star has yet to comment on.

Sweeney has, though, always seemed to have a thick skin, especially in the service of her dream.

And as she watches another glorious sunset over the water, from the deck of her mansion, with her billionaire boyfriend and loving family, she must reflect that her dream has come true in ways which even she did not dare to imagine.

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