He used to be a street kid. Now he has an apartment with a harbour view
Despite such a varied reputation, the softly spoken, well-dressed gentleman of 71 is baffled why anyone would want to interview him, let alone pay for his lunch. 'Surely, there are more interesting people?'
As we settle into the window seat of the Macleay Street Bistro, he makes a few jokes about whether we have the right 'John Howard', implying the Herald must have intended to sit down with the former prime minister who shares his name.
But this is no mistaken identity. As we both opt for sparkling water, I tell Howard that I first heard of him 20 years ago, when I was writing for the Herald's Domain, from a local real estate agent who talked about the guy who makes money buying car spaces and renting them out.
Howard's initial discomfort about having his photo taken is parlayed into ordering. We both want the garlic prawns, Howard has them for an entree with the pan-fried salmon for a main, and I order the French onion soup followed by the prawns as a main.
Food out of the way, Howard's demeanour lights up as he describes running away from his dysfunctional childhood in Baulkham Hills in Sydney's north-west to the bright lights and chaos of Kings Cross. The Yellow House artists cooperative was at its zenith, and the streets were full of hippies, prostitutes and soldiers on leave from the Vietnam War. 'It was fun, and mad, and I didn't want to be anywhere else.'
Among his first jobs was being a kitchen hand at Whisky A Go Go, and a bus boy at Chequers and the Bourbon and Beefsteak – all local landmarks.
'I was living the high life, in a low-life sort of way,' he said. 'To my mind I was racing around, having fun, trying to survive, and dreaming of buying the latest sports car and meeting the perfect girl.'
But in reality he was failing at everything, he said. 'I wasn't a gangster. I was a nuisance.'
Either way, the authorities began to take a keen interest.
In the early 1970s, Howard fell foul of a local pimp-cum-psychopath, so he decided to skip town by stealing a car and heading for Queensland's Morton Island. The plan being to single-handedly set up a hippie commune.
He made it as far as Wingham, west of Taree, before he was pulled over for throwing an empty carton of chocolate milk out the car window. A registration check upgraded the littering offence to car theft, and Howard was thrown in the local police cells.
He wasn't in the cells long. Howard's slight frame meant he was able to squeeze through the food opening gap to the police courtyard where he jacked the steel wire mesh out of the brickwork and escaped.
It was a successful getaway, for all of a week, before he was picked up by police, this time in Woolloomooloo stealing petrol from a car. 'Over the years I have made some poor choices,' Howard deadpans.
'I was living the high life, in a low-life sort of way.'
John Howard
Mental health and addiction issues didn't help, and they only worsened as he got older, even if he was oblivious to it. By 39 Howard was homeless, living in a laneway behind Central Railway Station. 'At the time I thought my problem was that I didn't have a job, but in hindsight I was drinking too much.'
One pivotal day, fate intervened in the form of a taxi driver who had taken a shortcut down Howard's laneway, and saw him lying in the gutter. Presciently, he knew just what Howard needed.
'He later told me he thought I was dead, but when he realised I wasn't, he took me to a bottle shop to get a flask, and dropped me at hospital,' he said. 'That kindness of a stranger saved my life.'
A series of hospital admissions followed before Howard was sent to the brain-damage unit at the now defunct Callan Park Hospital, where he remained for a year.
'It was a safe place where I didn't have to worry about feeding myself or that kind of stuff, and it took the pressure off the need to survive. I felt at home.'
More crucially, Howard met like-minded people who visited patients, and who he felt understood him and what felt like to be hopeless and self-destructive.
That support network remains a mainstay of Howard's life.
When he left Callan Park, he was handed second-hand clothes, given a 10-year disability pension and sent to live in a half-way house in Five Dock. Things were looking up.
'When I was offered a flat in a high-rise block in Redfern, I knew if I lived there I would fall back into my old ways, so I said no and approached a private housing co-op instead.' The co-op found him a pad back in Kings Cross.
It wasn't just Howard's circumstances that started to improve in the 1990s. Kings Cross's seedy strip joints, and budget hotels were fast coming to the attention of high-end developers.
The Harry Seidler-designed Horizon tower in Darlinghurst was the most notable of the early landmark developments, launched in 1998 and followed by Altair from now defunct architectural firm Engelen Moore in 2001, and Mirvac's IKON in 2005.
And Howard went to work, channelling what was once a fervour for partying into a work ethic that bordered on the compulsive.
There was the gift stall at Rozelle Markets, telemarketing for the Guide Dogs, and a long-time gig as the night manager at the budget hotel Springfield Lodge.
In 2000, a friend offered him one of the puppies from her poodle's litter. 'Now this was responsibility.'
In the months before Howard was due to pick up his puppy, Sunny, he took to learning everything about owning a dog: how to feed them, what they eat, how to train them, where they sleep.
'In the brain damage unit, I was given a pen and paper and told to write everything down because I couldn't remember stuff,' he said. 'So if I had to catch a bus, I wrote down the number, and from that I learnt to pre-plan everything.'
But amid all the dog research he missed the bit about cleaning up after it, as he discovered when Sunny did a poo in front of a big crowd at the El Alamein Fountain. 'In those days, all that was available were shopping bags or plastic pooper-scooper things.' So Howard started researching alternatives: smaller plastic bags of a certain thickness and colour.
'I tried sourcing it from Australian producers, but they weren't financially viable, so I approached three suppliers in China.'
A lucrative business was born, and peaked a few years later at $15,000 worth of sales a month.
According to Pet Barn, the 36-pack Poohy Bags product distributed by Howard was one of their most popular sellers from 2010 to 2014, before the market became crowded with more suppliers.
Sunny also brought bad news. The co-op flat didn't allow dogs so, served with an eviction notice, he decided to buy his first home.
Aided by what was then the $7000 first home buyer's grant and a mortgage, Howard purchased a studio in the Ganray building in 2001 for $110,000. 'I threw everything at that mortgage.'
The following year he purchased a car space in the Picadilly Gardens for $35,000, and another space a year later for $40,000.
By the time Howard purchased another studio in 2007 he no longer needed a mortgage, and hasn't required financial assistance since.
Over the years he has bought and sold eight car spaces, a couple of storage cages and two studios, sometimes for modest capital gains and sometimes for more. The first car space he bought in 2002 sold in 2021 for $105,000. His first home, the studio, almost doubled in value, to sell for $192,000 in 2009.
Today he retains five of those car spaces, one storage cage and his north-facing apartment atop the Clairmont building in Potts Point with harbour views. 'This isn't about becoming rich. It's just about being fully self-supporting.'
It also seems to bring a certain joy from doing business.
Not that the dreams of a young Howard have been neglected. When he leaves his neighbourhood he usually does so either his red 1948 MG TC or his blue E-type Jaguar.
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As we scoff dessert – chocolate truffles for me and vanilla ice-cream for him – Howard returns to his question about why I want to interview him. After all, for all his car spaces he is yet to make the pages of Title Deeds.
An articulate answer escaped me, but in retrospect it's because Howard's story is less about the good luck and bulging bank balances that are the calling cards of many of Sydney's property moguls, and more about the grace and redemption that has played out over his colourful life.

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