Dina Broadhurst and John Winning Jr Split Again

He's the company boss who likes to work hard and play hard.

But that not everyone at appliances company Winning Group was thrilled by CEO John 'Herman' Winning Jr's flashy lifestyle and 'rock star' Instagram posts, we fear we may have set the cat among the pigeons.

You see, John seems to have now deleted his Instagram account.

While there are many reasons why he might have done this, we noted in January that one particular shot of John and girlfriend Dina Broadhurst irked company insiders.

He was captured in a snap taken inside his walk-in wardrobe, dressed in drop-crotch pants, a leopard-print shirt and sunglasses that would make 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.

But his absence from Instagram isn't the only thing we've noticed. 

John hasn't appeared on socialite Dina's curated Instagram feed lately. It could simply be her respecting his privacy - or it could possibly be another break-up.

Dina, 50, and John, in his early 40s, have been dating on and off for about two years, but last August, Dina  that they had 'reconnected with a much deeper bond' and were 'happier than ever'.

Whether they remain so is now being questioned in the gossipy eastern suburbs.

If they have broken up, Dina hasn't exactly been living like a wallflower. 

On Monday evening, she uploaded an Instagram Story of a mystery man sitting opposite her as they dined at a restaurant. It disappeared after 24 hours, as all Stories do, but screenshots were soon being shared widely in elite Sydney group chats.

The Daily Mail has contacted Dina and John for comment and clarification on the state of their relationship.

'Herman', as he is widely known, is the son of appliances mogul John Winning Sr, whose family is worth an estimated $700 million.

In August 2025, Dina announced the couple were back on again (pictured around this time)