Insiders spill on Winning Appliances CEO’s rock-star lifestyle – and not everyone’s happy… Plus, exes’ court battle casts shadow over Bondi Boost wedding: THE GROUP CHAT

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Join Lucy Manly in The Group Chat for the latest Australian celebrity and society news – you’ll hear the buzz before anyone else!

Winning at life 

Don’t you miss the days when CEOs lived like rock stars?

John Winning Jr., the CEO of appliance company Winning Group, shows that philosophical thinking still matters in 2026.

Honestly, I’ve been keeping an eye on him, and it seems he’s really embraced a fun, vibrant lifestyle lately! Since January, he’s been spotted out and about partying with the amazing Yungblud, and his Instagram is full of super chic photos with his girlfriend, Dina Broadhurst – they just always look so effortlessly cool together. It’s a total vibe!

But there’s a problem.

Herman is a capable CEO, but some family members feel his social media isn’t quite professional enough for someone in his position.

One of Dina’s latest shots of the duo has particularly irked company insiders.

This week, a photo surfaced of Herman inside his closet, sporting a rather bold outfit: drop-crotch pants, a leopard-print shirt, and sunglasses flashy enough to rival Elton John’s.

The event felt more like a fashion show than a presentation by the heir to an appliance company, and it wasn’t the refined, presidential image some people on the campaign team were hoping for.

Insiders reveal that Winning’s leaders wanted Herman to appear more dignified and presidential, suitable for leading a well-known company. However, he comes across as someone who simply works and plays intensely.

Things are now stable in Herman’s love life. He and Dina are officially back together after a rocky period that began around April 2024.

Dina definitely enjoyed some perks from her on-again, off-again relationship. When things were temporarily over last year, she started dating a model in his twenties. Good for her!

Snow much fun 

The billionaire ski playground of Aspen took on a distinct Australian twang this season.

Barbara Coombes, a prominent figure in Sydney society, and her husband Michael, a property developer who people often compare to actor Jason Statham, were at the forefront of the effort.

The couple was seen having fun with Orlando Bloom, who welcomed them warmly. They started the evening with dinner at the popular Sant Ambroeus restaurant, and then the group – including Charlie and Wallis Graham – continued the party at Silver City, a famous and lively bar in Aspen known for attracting celebrities.

It wasn’t long before Babs’ niece was singing “Total Eclipse of the Heart” with Bloom in a karaoke duet.

The actor was spotted out with friends just a few days after turning 49. Sources say his birthday party included him leading a lively conga line of prominent LGBTQ+ individuals.

Babs and Michael’s trip to Aspen was also a family vacation. They were joined by Babs’s father, Terry Tzaneros, who owns a freight and transport company, as well as her brother Arthur and his wife, Maude. Michael’s sister, Angelique Andrews, a well-known socialite, also came along.

Dexies drama 

Kelly Smythe, a well-known fashion stylist and socialite from the early 2000s, appeared in court this week. She pleaded guilty to obtaining drugs from a pharmacy in Paddington using a forged letter and two fake prescriptions.

The 48-year-old woman, a resident of Point Piper’s most expensive street, had her charges dismissed in court due to mental health concerns. However, this followed a guilty plea for improperly using prescription medications, and she was required to begin a treatment program.

Okay, so I’ve been digging, and it turns out those prescriptions everyone was talking about? They were for Adderall and Vyvan – seriously! The documents say they came from Paddington Compounding Pharmacy last year. I knew something was off, and now we have proof! It’s just… unbelievable. I’ve been following this so closely, and this is huge!

Dextroamphetamine, commonly called ‘dexies,’ is usually prescribed for conditions like ADHD and narcolepsy. Lisdexamfetamine treats adults with moderate to severe binge eating disorder. Smythe, however, wasn’t authorized to prescribe either of these medications to themself.

When Smythe tried to pick up her prescription at the pharmacy for the last time, police were there to arrest her. The arrest occurred on May 15, 2025.

Stephen Alexander, a leading Sydney barrister, told the court that Smythe’s actions were a result of his depression.

‘It was self-medication,’ he reportedly said, insisting she was only harming herself.

He also mentioned Smythe might have ADHD and was receiving medical treatment. The court heard that she felt she needed more medication to help her recover.

Police prosecutor Sergeant Will Bargwanna didn’t accept the explanation, noting this wasn’t a single incident, but a pattern of behavior lasting eight months.

Despite everything, Smythe persuaded Magistrate Jennifer Atkinson, who acknowledged her mental health struggles and required her to begin a structured treatment program. However, the magistrate first made it clear she wasn’t qualified to give medical advice.

Bad neighbours

A scheduled court hearing last month was missed, though it likely should have been remembered. The case involved a particularly notable divorce in one of the city’s eastern suburbs.

Michael Burn, who used to work as a male escort and is engaged to Alexandra Jakob (the founder of BondiBoost), appeared in court on December 12th to address legal issues involving Alexandra’s former husband, Gabriel Jakob.

Alexandra and Gabriel were a couple for twelve years and built a successful childcare business together. They separated in May 2023.

Most couples who split up move away from each other, but John and Alexandra Jakob continued to live next door as neighbours, each in a large house on Wolseley Road in Point Piper. However, that’s changed now, as Alexandra has recently moved to the other side of the harbour.

Following her divorce, Alexandra began a relationship with Mr. Burn, and they eventually got engaged. They were planning to get married in September at the historic Grantley Hill estate in the Yorkshire Dales, England.

Things haven’t been easy between the ex-couple, the Jakobs, and the new partner, Mr. Burn, who notably has a tattoo of Alexandra’s name on his chest. They haven’t formed a peaceful or happy relationship.

I was so relieved to hear that the court granted a domestic violence order to protect Gabriel. After the hearing on December 12th, it means Gabriel is safe from Mr. Burn for the next five months, and that’s a huge weight off my mind.

The court order prevents Mr. Burn from contacting or approaching Gabriel – who prefers to stay out of the public eye, even declining to have his face shown in a recent positive article – except through his legal representatives. It also forbids him from any form of violence, harassment, or intimidation. This order simply sets standard conditions, and there’s no indication from available information that Mr. Burn has actually done any of these things.

Two stalking charges against Mr. Burn, involving Gabriel, were dropped after he denied them in court. He admitted to a third charge, but the judge chose not to convict him.

Sadly, that’s not the end of the saga.

Mr. Burn has another court date scheduled for February 17th. This time, he’s the one requesting an Apprehended Violence Order (AVO) against someone who is not Gabriel Jakob.

And March 23 sees Alexandra listed in separate proceedings.

Also, a legal case involving the former Sydney couple is still in progress. You can find details about it here.

 

New to DailyMail+? Here are our most-read stories from the last week

As a lifestyle expert, I’ve been following this story with a lot of interest. It’s fascinating – and frankly, a little disheartening – to see how a group of Sydney’s established socialites have turned on a mum-of-three who’s built a following online. What started as seemingly harmless social interactions has devolved into some pretty nasty behavior, playing out in private group chats. I’m diving into the details – including the specific clip that apparently sparked all the drama – and, most importantly, giving the influencer at the center of it all a chance to share her side of the story. It’s a real look at the pressures of social circles and how quickly things can turn toxic.

It’s sadly predictable to see privileged women cruelly mocking a young mother. A recent exchange in their private messages revealed a common, yet dishonest, belief held by many Australian women, as highlighted by Amanda Goff.

What a surprise! The story surrounding Lachie Neale has taken another turn, with Tess Crosley spotted visiting his home. Meanwhile, Jules’ new manager is addressing gossip about reality TV.

Disturbing photos from the Idaho murder case have been leaked, showing the victims shortly before their deaths. The images offer a glimpse into the final moments of their lives and are connected to suspect Bryan Kohberger.

A woman who was harmed by Tom Silvagni has spoken out strongly after a disturbing claim was made about her private life. This comes as Silvagni’s son challenges his legal conviction.

Australia’s wealth gap is getting attention thanks to a newcomer challenging established social circles. Here’s a breakdown of who fits into ‘old money’ versus ‘new money’ categories.

Tennis star Nick Kyrgios appears to have a preference for a certain look, as his new girlfriend, spotted at the Australian Open, bears a striking resemblance to his former partner, Costeen Hatzi.

Sources reveal the tensions between the Beckhams and Nicola Peltz, detailing concerns about Brooklyn’s seemingly immature behavior towards his wife, a specific incident that upset the Peltz family, and the story behind a reportedly awkward dance between Brooklyn and Victoria Beckham. This article by Alison Boshoff explores the reasons behind the strained relationship.

Here’s the inside story on Luke Sayers’ legal battle and how it threatens the stability of the Australian Football League. Plus, the women involved in the Lachie Neale situation are discovering shared perspectives, according to Costello’s report from Melbourne.

Katie Hind reveals the inside story of Brooklyn and Nicola Peltz Beckham’s wedding, including details about a controversial dance, inconsistencies in the Vogue coverage, and a shocking bathroom incident that upset the Beckhams.

Chumpy Pullin’s father has spoken out about a rumor spread by supporters of Ellidy Pullin, Chumpy’s widow, concerning his relationship with a younger woman. He claims the rumor, which he called ‘ridiculous,’ arose after he publicly discussed a family dispute.

My world completely crumbled when I swapped alcohol for what I called my ‘mummy treat’ – a drug I thought would help me cope. It ultimately led to losing my children. Now, I’m sharing what I’ve learned, the subtle signs I wish I’d recognized in the parents around me at school. Victoria Vigors is helping me spread awareness, and I want to help others see the warning signs too.

Recent divisions in society are fueling conversations about a man known as ‘Mr Perfect’ in Bondi. We’re sharing the latest gossip. Plus, we investigate the past of a French model facing drug charges and explore the romance between a prominent club owner and someone much younger – all in today’s headlines.

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2026-01-29 15:53