The party boy CEO, his 'cougar' - and wild corporate whispers behind Winnings: Insiders reveal the eccentric playboy behind the ritzy showrooms - and his plans for when he gets his golden parachute

By LUCY MANLY, SENIOR NEWS REPORTER, AUSTRALIA Published: 15:20, 3 May 2026 | Updated: 15:20, 3 May 2026 Sydney businessman John Winning Jr, better known to his high-society friends as 'Herman', is poised for an even larger fortune following investment giant Ellerston Capital's $100million investment in the family business he inherited, Winning Group. It's a deal that further cements the Winnings' place among Australia's great dynasties. This week, the blue-chip investor officially closed its nine-figure investment, delivering a substantial windfall to the Winning family. The transaction comes as Ellerston positions the whitegoods empire for a potential ASX listing later this year. It's not bad for a family built on fridges and dishwashers. The AFR Rich List estimates the Winning clan's fortune at an impressive $770million. But while the balance sheet is looking healthier than ever, all has not been entirely gleaming behind the fancy showroom doors. Sources close to the board say the company has spent the past year grappling with cultural issues, executive turnover and what some privately describe as erratic leadership. At least a dozen senior executives have departed in the past six months, including sales chief James Moore, chief operating officer Trent Allan, marketing head Fraser Gardner, New Zealand general manager Troy Tindill, design boss Kate McGlone and client services manager Carey Tisdell. Sydney businessman John Winning Jr with his on-again, off-again 'nude artist' girlfriend Dina Broadhurst. His colourful personal life was well-known within the family firm, with this Instagram photo in particular raising eyebrows John 'Herman' Winning with his father John Winning Sr (right) Last year, he reportedly insisted that Broadhurst's artwork be displayed in Winning's flagship showroom. Broadhurst's work is renowned for incorporating her own naked form Within the business, some staff have quietly questioned whether Herman's attention has drifted beyond the boardroom, with DJ gigs in New York, wingsuiting and skydiving among the keen sailor's many extracurricular pursuits. Last year, he reportedly insisted that the artwork of then-girlfriend Dina Broadhurst be prominently displayed in Winning's flagship showroom. Broadhurst's work is renowned for incorporating her own naked form into intricately layered collages, earning her the nickname 'the nude artist'. Their high-profile romance is also said to have caused some headaches among top brass, particularly when Herman's social media persona seemed to project more Ibiza party boy than boardroom leader. Notably, he brought Broadhurst, with whom he is no longer in a relationship, along to a company retreat to New Zealand. Her posts from the trip, captioned 'NZ vibes' and featuring a Winning Group lanyard visible in one photo, did not go unnoticed. Broadhurst is now dating younger German entrepreneur Danny Tchalaby. Of course, Herman has long cut a colourful figure. The eastern suburbs playboy resides in a famously eccentric Surry Hills warehouse, complete with a private nightclub, gold bar, glass smoking room, swimming pool overlooking the dance floor and a UFO-shaped sleeping pod adorned with mirrors. Staff quietly questioned whether Herman's attention drifted beyond the boardroom, with DJ gigs in NYC, wingsuiting and skydiving among the keen sailor's extracurricular pursuits He reportedly also insisted on bringing Broadhurst, with whom he is no longer in a relationship, along to a company retreat to New Zealand Broadhurst captioned this Instagram gallery from October 2025 'NZ vibes'... Zoom in on the frame and a Winning Group lanyard is clearly visible, revealing it was a business trip rather than a couple's holiday Not long ago, he was photographed partying on Sydney Harbour with Broadhurst and British rocker Yungblud. It was hardly the typical look for a company CEO. Since then, his split from Broadhurst, followed by a romance with Big Brother star Holly Young, has generated headlines unlikely to impress Winning's top brass. In a telling recent move, Herman appears to have deleted his Instagram account. Herman has already agreed to step aside as chief executive once a replacement is appointed, a move that should reassure Ellerston as it prepares the business for its next phase. With roots managing Packer family money, Ellerston has built a formidable reputation backing successful growth companies including Firmus, Yo-Chi, HiPages and HUB24. Investor sources suggest a significant portion of the fresh capital will ultimately be distributed to Herman, giving him even greater freedom to pursue his many interests. And among those, sailing remains paramount. Broadhurst is now understood to be dating younger German entrepreneur Danny Tchalaby After splitting from Broadhurst, Herman reportedly romanced Big Brother star Holly Young  Herman learned the ropes at the Vaucluse Amateur 12 Foot Sailing Club, became a 29er world champion at just 18, and later raced 18-foot skiffs sponsored by Appliances Online. Some suspect this latest windfall may see him devote even more time to yachting and racing - pursuits perfectly suited to a man whose home already includes what can only be described as a mirrored spaceship. Which leaves the obvious question: will Herman remain central to Winning's ASX ambitions, or will he, as many quietly suspect, sail off into the sunset? Another whisper doing the rounds in the eastern suburbs: with his payday on the horizon, will Broadhurst drop her latest toyboy and run back to her old flame - just as she has before? No comments have so far been submitted. Why not be the first to send us your thoughts, or debate this issue live on our message boards. By posting your comment you agree to our house rules. Do you want to automatically post your MailOnline comments to your Facebook Timeline? Your comment will be posted to MailOnline as usual. Do you want to automatically post your MailOnline comments to your Facebook Timeline? 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