Welcome to The Group Chat with Lucy Manly, where Australia’s premier society insider dishes out the juiciest gossip before it hits the headlines.

Winning at life 

Remember when CEOs were the rock stars of the corporate world? Well, those days are far from over, at least if John ‘Herman’ Winning Jr has anything to say about it. As the CEO of the Winning Group, a leading appliances company, Herman is living proof that the rock-and-roll lifestyle is alive and well in 2026.

Since the beginning of the year, Herman has been spotted living it up with British rocker Yungblud and striking a pose in effortlessly cool selfies with his socialite girlfriend, Dina Broadhurst. The snapshots of his vibrant social life have made quite the splash.

However, not everyone in the family business shares Herman’s enthusiasm for his public persona. While no one questions his competence as a CEO, some within the company wish his social media presence would reflect a more traditional, corporate image.

But there’s a problem.

While Herman is, by all accounts, a perfectly competent CEO, there are some within the family firm who wish his social media presence would be a little more… CEO-like.

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

This week, Herman was captured in a snap taken inside his walk-in wardrobe (yes, really), dressed in drop-crotch pants, a leopard-print shirt and sunglasses that would make Elton John jealous.

It was certainly more Fashion Week than appliances heir, and not the sort of polished, presidential look some within Winning HQ would quietly prefer.

Sources say Winning top brass had long hoped Herman would cultivate a more statesmanlike presence befitting the helm of a household-name company. Instead, he projects an image of ‘work hard, play harder’.

Still, at least things have settled down in his romantic life. After being on and off since at least April 2024, Herman and Dina are now firmly back ‘on’.

Dina certainly reaped the benefits of their yo-yo love story, hooking up with a Belgian model aged in his 20s during one of their ‘off’ periods last year. You go, girl.

Snow much fun 

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

Leading the charge was Sydney socialite Barbara Coombes and her property developer husband, Michael – a man often mistaken for English actor Jason Statham.

The pair were spotted partying with Orlando Bloom, who happily embraced the Aussie invasion. Festivities kicked off with dinner at glitzy hotspot Sant Ambroeus, then the group – including corporate advisor Charlie Graham and his wife Wallis – later migrated to Silver City, Aspen’s storied mountain saloon and celebrity haunt.

Before long, Babs’ niece found herself sharing the microphone with Bloom for a karaoke rendition of Total Eclipse of the Heart.

The outing came mere days after the Hollywood star’s 49th birthday, which reportedly saw him leading a conga line of ‘power gays’.

The Aspen escape doubled as a family affair, with Babs and Michael hitting the millionaire ski fields flanked by her father, freight and transport boss Terry Tzaneros; her brother Arthur and his wife Maude; and her socialite sister-in-law Angelique Andrews – who, for good measure, is also sister to Michael Coombes.

Dexies drama 

Former stylist and 2000s ‘It’ girl Kelly Smythe faced court this week after admitting she used a false letter and two fraudulent prescriptions to score drugs from a Paddington chemist.

The 48-year-old, who calls Australia’s most expensive street in Point Piper home, appeared at Downing Centre where the charges were ultimately dismissed on mental health grounds – but only after she pleaded guilty to misusing multiple pharmaceutical scripts and was formally ordered into a treatment plan.

Court documents revealed the dodgy prescriptions were for dextroamphetamine and lisdexamfetamine, obtained from Paddington Compounding Pharmacy last year.

Dextroamphetamine – better known as ‘dexies’ – is typically prescribed for ADHD and narcolepsy, while lisdexamfetamine is used to treat moderate-to-severe binge eating disorder in adults – neither of which Smythe was authorised to self-prescribe.

The court heard that the final time Smythe attempted to collect medication from the chemist, police were waiting. She was arrested on May 15, 2025.

Represented by one of Sydney’s top barristers, Stephen Alexander, the court was told Smythe’s offending was driven by depression.

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

He also suggested Smythe may suffer from ADHD and had been under ongoing medical care, telling the court that, in her mind, she believed she needed additional medication to ‘rehabilitate’ herself.

Police prosecutor Sgt Will Bargwanna wasn’t buying it, pointing out the behaviour wasn’t a one-off slip, but one that stretched across an eight-month period.

Still, Smythe managed to convince Magistrate Jennifer Atkinson, who accepted her mental health issues and ordered her into a formal treatment plan – though not before issuing a stark reminder that she was not a doctor.

Bad neighbours

A court date slipped by last month without much notice. But it probably shouldn’t have, because it involved one of the eastern suburbs’ more compelling marital splits.

Michael Burn, a former male escort and the fiancé of BondiBoost entrepreneur Alexandra Jakob, appeared before a magistrate at Downing Centre on December 12 over several matters related to Alexandra’s ex-husband Gabriel Jakob.

To recap: Alexandra and Gabriel were together for 12 years and made a fortune from childcare centres before separating in March 2023.

While many former couples opt for a clean break, the Jakobs remained neighbours, occupying tri-level mansions on Wolseley Road in Point Piper. The arrangement no longer stands, with Alexandra moving across the harbour.

After the split, Alexandra found love with Mr Burn, and the pair later became engaged, with plans to marry at the 17th-century Grantley Hill in England’s Yorkshire Dales in September.

Unfortunately, the former Mr and Mrs Jakobs and her new partner Mr Burn – who has Alexandra’s name tattooed on his chest – have not made for a harmonious trio.

The upshot of the December 12 hearing was an apprehended domestic violence order made to protect Gabriel from Mr Burn for 12 months.

The order prohibits Mr Burn from contacting or approaching Gabriel – a man so media-shy he wouldn’t let the AFR show his face in a glowing 2024 profile – except through lawyers, and from engaging in any form of assault, harassment or intimidation. (The Group Chat does not suggest Mr Burn has done any of these things, only that they are the standard conditions of the AVO.)

Meanwhile, two charges of stalk/intimidate against Mr Burn related to Gabriel were withdrawn after he pleaded not guilty. He pleaded guilty to a third but the matter was dismissed with no conviction recorded.

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

Further court dates loom. Mr Burn is due back in court on February 17, this time as the party seeking protection in an AVO application against another person who, I should note, is not Gabriel Jakob.

And March 23 sees Alexandra listed in separate proceedings.

Oh, and a separate Federal Court matter between the former Sydney power couple is still ongoing. You can catch up on that mess here.

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