Annette Sharp: John Singleton relaxes in Hawaii with Venessa Merrin and Michelle Leslie

Sydney businessman John Singleton has escaped lockdown to his Hawaiian summer house and is kicking back with two of his favourite lady friends, writes Annette Sharp.

Two years after splurging on a Hawaiian summer house two doors up from Barack Obama’s former retreat, Sydney businessman John Singleton is finally ensconced in his remodelled retirement pad, where he’s said to be enjoying the company of two attentive lady friends.

The legendary ad boss-turned-media investor, who banked around $81 million after selling out of radio network Macquarie Media in September 2019, flew to Oahu two weeks ago to escape Sydney lockdown and inject some old-school Aussie flair into his presidential new neighbourhood.

John Singleton and Venessa Merrin.

Interior decorator Michelle Leslie.

Sources close to the six-times-married “Singo” have told this column the multi-millionaire is well-attended at his new $9.3 million home, with his on/off girlfriend Venessa Merrin in residence along with the interior decorator Singleton has patronised almost exclusively for the past 12 years, ex-model Michelle Leslie.

Leslie’s relationship with Singleton has intrigued close friends — and family — for years.

Singleton last year admitted he “loves” the one-time Miss World Australia 2000 pageant runner-up and former partner of Silverchair frontman Daniel Johns.

He assured us, though, that his relationship with Leslie, who is 40 years his junior, is purely platonic.

Leslie has been spending time in Hawaii …

… posting pictures on her Instagram account.

“We have some of the best times ever … but serious it is not,” he said of the former Bali party-girl he has helped professionally rehabilitate.

It’s a friendship that has worried some of Singleton’s children, with Leslie spending months at a time living between their father’s luxury homes in Hawaii and Mt White, the horse stud north of Sydney he also paid her to redecorate.

Concern peaked last year when Singleton revealed he would name his Hawaiian property “Shells”, although he assured this writer he was doing so not because it was Leslie’s nickname but because “I have always loved seashells …” — a response that had a few of
his manlier mates chortling into their beer.

Leslie has been a virtual artist in residence at “Shells” since Singleton bought the 1935 shingled bungalow plus cottages on a 1300sqm oceanfront block on Lanikai Beach.

Merrin and Singleton have been on-again off-again since they met in 2015. Picture: Luke Marsden

This year she has repeatedly posted images from Hawaii to social media. In one, uploaded in April, she is seen walking solo on a beach in signature Panama hat and bikini.

With Singleton not returning calls last week there is no word on whether his beloved dogs, a pair of Rhodesian ridgebacks, have also accompanied their owner to Hawaii for this trip.

Part of the island’s appeal is said to have been softer quarantine legislation concerning dogs being transported from Australia.

Merrin, who works in New York at a media group but was schooled in Melbourne, has enjoyed a romantic renaissance with Singleton during the past year.

After reuniting in Australia with the infamous six-times-married ladies’ man last November, the blonde, who has been linked to Singleton since 2015, was on his arm at the March wedding of 2GB radio presenter Ray Hadley to Sophie Baird.

Singleton has told friends he’s planning a three-month stay in Hawaii, returning after he turns
80 in November, a milestone many hope he will celebrate with a house-warming party in the
Aloha State.

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