The bad boy of hospitality is nearing retirement age, yet his capacity for bitter feuds remains undiminished. Duncan Greive meets Leo Molloy, the Viaduct’s best host and worst enemy.

“I know Bernie Monk,” said Leo Molloy. “He was a year ahead of me at school.” I had barely sat down at Headquarters, Molloy’s Viaduct restaurant before he, unprompted, brought up the longtime spokesperson for the Pike River families, whose son Michael died in the 2011 tragedy. “[Monk] has this craven desire to be in the media,” he says. “I feel sorry for him obviously. But he’s milked it in the extreme.”

There are few individuals who, on meeting you, would launch into a tirade against one of the most sympathetic figures in the country. Within minutes he’d done the same to Andrew Little (“lunatic”), Jesse Mulligan (“all sizzle no sausage”) and the Herald (“toxic”). Making statements on a spectrum running from eye-opening to appalling is just everyday life in what Molloy calls “Leoland”. He’s a youthful 63, wears ripped jeans and open shirts and looks you dead in the eye as he speaks, as if wanting to analyse your reaction to his statements in real time.

Even by his standards he’s been saying a lot lately. He lit into The Project over their coverage of a customer complaint, saying “I will do whatever it takes to hurt people until I really hurt you badly… I will seek to extract maximum revenge in every way possible.”

A week later he was at it again, responding to his nomination for a hospitality award with a diatribe against other nominees in the ‘outstanding establishment’ category.

“Soul, that place where the old white people hang out with girls with flappy lips, sugar daddies, and car salesmen, some sugar daddies who are car salesmen,” he wrote, “where they still serve salt and pepper squid with curry sauce, then there’s Prego, that’s that nursery for young mums in active wear with screaming babies in Ponsonby.”

Last week it was the Sugar Club and Sky City, “god awful… parasitic consortium”. Last year it was league fans, “low league following scum… you dogs, you vandals and you abusers.” The year before, Hamilton’s Good George: “a second-rate shithole operation”. He’s come for racing officials and MasterChef contestants, astrologers and journalists, on and on, stretching back for decades, vicious invective sprayed at anyone who crosses him.

Molloy is not some crank on the fringes of the industry. His restaurant and bar, Headquarters, is “by far the biggest” such establishment in New Zealand, according to Molloy. “We’re seven times bigger than the next biggest champagne retailer,” he says, and while his supplier would not confirm that statistic, they did acknowledge Headquarters as “one of our top-selling accounts”.

It sits on what is probably the best hospitality site in the country, alone in a sun-drenched corner of Auckland’s Viaduct. It’s a honeytrap for prominent New Zealanders having a good old time, from politicians to sportspeople to the business elite, and Molloy is always at its centre, sending across food, stopping by their table, ensuring they all feel loved.

Headquarters is hardly his first success, either – iconic or infamous venues with names like Cowboys, Euro and Danny Doolans have functioned as the fulcrum of various boozy Auckland scenes over the years. By any measure he’s one of the most successful hospitality entrepreneurs New Zealand has ever seen.

I wanted to know how he could be so enormously successful, so beloved by so many important people, while so often being such a gaping arsehole. After he sent some strange emails to The Spinoff, I asked the famously anti-media Molloy if he was prepared to be interviewed. Somewhat to my surprise, he readily agreed.

There was only one condition: that I read the story of Headquarters, printed on its menu, before we speak. On a sunny afternoon in mid-May, I headed down to the Viaduct to do some reading. It detailed the brighter spots in Molloy’s hospitality backstory, before setting out a manifesto. What the kitchen puts out is “brutally honest… no silly bloody flowers on your food, the molecular foam or the sparrow sized servings”, and nods at ambience with “our music is loud… don’t be afraid to boogie”.

Much of it takes on Leo’s pet hates, at the time The Project and the Labour Party (“Ponsonby politicians [who] want to ban cigarettes but make weed legal”). It’s a deliberately obnoxious piece of writing, especially as it’s the first thing diners see on being handed a menu. Where its pricey neighbours often strain to reflect class and sophistication, Leo Molloy’s operation, much like the man himself, seems grimly determined to do the opposite.

Molloy was hesitant about recounting his life story. “It’s actually really fucking boring,” he said. But it’s not, and eventually he agreed to tell it. He was born and raised on the West Coast of the South Island, the second eldest of seven children. “Mum worked in the mines, Dad was a soldier,” he says, the latter working as a mechanic after the war. “They married when Mum was only 19, as Irish Catholics do on the West Coast.”

The family lived in Moana, a tiny town at the northern tip of Lake Brunner. When Molloy was seven, his father Kevin had a stroke, and he was thrust into the role of carer. “Dad always called me his ‘right-hand man’,” says Molloy, who had to wash and dress him in the aftermath.

After the stroke, the Molloys moved to Moonlight, a small town alongside Pike River, where Kevin worked on the boilers at Stillwater. His mother Maureen worked in the Roa mine, near Blackball, the birthplace of the Labour Party and spiritual home of the labour movement. He says the family home was “very loving, very Irish”. This background is crucial to his sense of self – “we’re fourth generation [immigrants], but still pure-bred” – and Molloy describes the Irish as never happier than when living with tragedy.

The Molloys got theirs when Kevin died at 47, of a brain haemorrhage. Molloy was 11. “By the time I was 12, I’d found a proxy father, and an industry I was interested in,” he says. “It was the horse-racing industry. And the reason I found it so compelling was that all the grownups ever talked about was sex, alcohol, or smoking cigarettes. Those were three of my lofty goals at that stage. So I embraced that with a huge appetite.”

Molloy left school at 15, and became an apprentice jockey. After four years he “got fat”, and, unable to ride horses, took a couple of years travelling to regroup. While in the UK he applied for vet college back home at Massey, but was rejected due to insufficient academics. He returned home to the West Coast and enrolled at Greymouth High School. “I managed to shag a couple of teachers, one teacher’s wife and about 10 students,” he says. “It was a great time.” It was 1980, and Molloy was 25.

He stayed two years, then went to vet school and eventually graduated and worked at his own small practice. Around the same time, New Zealand was slowly waking up to the implications of the Sale of Liquor Act of 1989, which massively expanded the number and scope of licensed premises. Molloy and his first wife (he married in 1991) took over a student bar named the Fat Ladies Arms in Palmerston North in 1991, changing the music and interior. It was a huge success, eventually becoming a franchise which peaked at nine locations.

He had found his calling. “I can chat to anybody,” he says of the secret to his success. “I’ve got that Irish thing, I can talk shit.”

In 1998 he headed to Auckland. When asked why, he pauses for a long time – a rare occurrence. “This is brutally honest time,” he says. “I’d had an affair.” He and his wife moved north to try and escape the aftermath, but couldn’t get past it. Rather than being cowed by the end of the marriage, he “viewed it as a great opportunity”.

“I’m a diamond,” he says, over and over. “The more pressure you put on me, the more I sparkle. Every time I’ve had a significant setback in my life, I come up with a diamond in my mouth. I did Euro about six months after she left me.”

A restaurant on the water alongside the Hilton, Euro became an icon of the emerging Auckland restaurant scene, arriving just as the Viaduct and America’s Cup were poised to create a new, monied party crowd downtown. The restaurant made him both host to and a member of a new, rich, flashy crowd. “I was balls deep in that,” he says. “Everyone was shagging everyone else’s partners. Everyone had an amazing life. One year 40 of us went to the Melbourne Cup. Hired a couple of floors of the Melbourne casino. Playing golf every day.”

This very quickly became Molloy’s life, helicopters and champagne and celebrities, a culture of conspicuous consumption that now seems dated, but was then all the central city aspired to. Today its last great bastion is Headquarters, where the leading lights of the era still keep the flame alive.

At its peak, the scene was acidly chronicled by gossip columnist Bridget Saunders in the Sunday Star-Times, and celebrated by the NBR’s rich list. Euro was its stage, its beating heart.

“I don’t know how I got it so right with Euro,” he says. “But I got it awfully right.”

On a damp Friday night early in June, a queue formed outside Headquarters at around 11pm. The place was pumping, just the right side of uncomfortably full, though Molloy told me the following day that it did only 35% of its peak turnover – “relatively quiet”. It’s a hospitality Frankenstein, open from 11am until very late, fine dining at one end, a whisky bar in the middle, a sports bar that becomes a dancefloor at the other.

The tension creates a customer experience that can seem almost comically bad – speakers drowning out conversation while dinner is served, and an epic battle through the dancefloor to the bathroom for diners. Yet the staff are attentive and accommodating, which helps smooth its edges. Besides, for Molloy, the only proof of a destination’s worth is its popularity, and by that measure it’s inarguably a success.

At midnight the dancefloor is packed, filled with people in their thirties and forties dancing and drinking with an abandon many of the new Viaduct venues seem designed to discourage. Over on the dining side, a large U-shaped couch is filled with a set of TVNZ employees who’ve been there since early evening. It’s hard to find anyone who isn’t having a good time.

The Viaduct is going through one of its periodic softenings, perhaps as a result of a large influx of new venues like Saint Alice and Dr Rudi’s, and very few have much of a queue. At Headquarters, the queue is out the door. I lined up behind Devin Patuawa, a young, sharply dressed visual merchandiser, and told him I was writing a story about Molloy.

“I hear he’s a real cunt,” he said, his eyes shining. This word hangs around Molloy. “I’m an absolute cunt with a capital C,” he said on a call with The Project’s producer Jon Bridges. Kirsty Kilgour has worked for Molloy for over a decade, describes him as a “mad genius” and seems to genuinely love his rough edges. “I wanted to get staff t-shirts for winter that read ‘my boss is a cunt’,” she says. He regularly refers to himself that way, and more regularly to others perceiving him as one.

The reputation has been hard-earned over decades. In 2002 he was fined $7000 by the employment tribunal for unjustified dismissal after physically restraining waitress Melanie Cheung from transcribing what he was saying to her. There was an incident involving astrologist Don Murray, who has published bizarre insinuations about Molloy over a period of years, and pro boxer Sean Sullivan, which made Rachel Glucina’s ‘best tiffs and tantrums of 2009’. And in 2014 a long-running defamation proceeding against Molloy, brought by racing executive Greg Purcell, was settled for a six-figure sum and an apology from Molloy. “My claims were baseless,” his statement read.

Throughout all this, his businesses careened onwards. As Euro swelled, so did Molloy’s myth. “It was so intoxicating. Suddenly going from being nothing, a nobody who never got invited to a party, to being on everybody’s dance card. Everybody’s. I mean everybody’s. Even [billionaire Oracle CEO] Larry Ellison had me out on his boat.”

At the same time, his love life picked up again. “I met another amazing woman. Got married, had five kids,” he says. “She’s gone too now.”

Euro was the stage for a frenetic decade for Molloy. Buoyed by its success, he set up Danny Doolans, “named after my grandfather”, an Irish pub that became another hit.

“I had such a good run, I thought I could just do anything.” He poured himself into one of the most ambitious ventures New Zealand had seen to that point: a huge, two-level club called Cardiac. Even by the standards of the time, it was extreme. There was a secret “naughty bar” through the toilets, which were unisex. “We put facilities in, so if you wanted to shag, you could do it.”

Cardiac was a significant departure from what he knew, away from his Viaduct stomping ground, in a beautiful heritage building on the corner of High and Shortland Sts, at the bottom of the towers full of lawyers further up the hill. “I thought there’d be a whole lot of suits come after work to drink, I’d give them a modest little feed. They’d go home and I’d make a lot of money. Didn’t happen.”

He hired pricey DJs like Roger Perry, at the peak of Auckland’s house scene, and hosted hundreds of people, yet “at the end of the night, the tills were empty”. Cardiac coincided with ecstasy and cocaine flowing into the city and quickening the pulse of its nightlife. “They mostly came to snort and drink water, and I just didn’t know what to do.” It’s not hard to imagine that his current opposition to drug liberalisation comes from the bitter experience of hosting full rooms of people high on someone else’s supply.

In November of 2003, he was declared bankrupt, owing over $1m, in part due the Cardiac fitout, which he described at the time as “fairly adjacent” to $2.5m. It was a huge setback for Molloy, one which saw him lose the social capital he’d gained, and from which he took years to recover.

In April of this year, Headquarters hosted an afternoon event, one only Molloy could have dreamed up or staged. A fundraising auction, featuring a who’s who of New Zealand political, sporting and media elites: Graham Henry, Paula Bennett, Stephen Fleming, Lance O’Sullivan, Shane Jones, Don Brash, Duncan Garner and more. Tickets were $150 a pop, which bought you “lamb and piglet banquet”, pavlova for dessert and “beer and bubbles as required”: a fantasy of 90s New Zealand excess.

Attendees bid on the chance to have lunch with the various celebrity groups, mostly clustered by background: cricketers, Crowd Goes Wild hosts, league players, Dancing with the Stars judges, Brian and Hannah Tamaki. (Molloy has lately become acquainted with the Destiny Church founders and attended a recent service.)

The final item on the agenda was also the most bizarre: a meal with Hone Harawira and Don Brash. When first asked, Harawira’s response was as you’d expect. “Fuck off, I’m not doing that.”

Then Molloy reminded him of the cause. The fundraiser came about after Harawira met Molloy while dining at Headquarters a few months earlier. The former Mana party leader told his host about TaiTokerau rugby league, a breakaway competition he’d helped set up in the far north. Run on passion, completely lacking in funds. “If I do a raffle up here, I’ll make $35,” Harawira told Molloy.

That night, Te Tai Tokerau rugby league ended up $75,000 richer. A transformative sum. “I couldn’t dream of that kind of money,” says Harawira.

Despite the ideological gulf between the pair – Molloy describes himself as a “Darwinist, basically”, Harawira’s Mana Party advocated for nationalisation of monopolies and duopolies – they get on well. “He’s a go-getter, kind of like me,” says Harawira. “He’s not a person to sit around on his arse.” Harawira met Owen Glenn at the auction, who offered his boat for the lunch date with Brash. So it came to be that a firebrand of the left headed out on a superyacht, after an event organised by a committed Tory, for the benefit of some of New Zealand’s most impoverished children. 

The lunch is not Molloy’s only charitable endeavour: currently 50% of the proceeds of Headquarters’ Sunday dinners are donated to organisations such as the City Mission. Former National Party president Michelle Boag is a neighbour and friend of Molloy’s and helped organise the auction. She says he’s “incredibly generous”, but a “flawed character”.

“He’s a constant doer, therefore he makes mistakes. But people who don’t make mistakes don’t do anything,” she says. “Leo has lived about five lives.”

After the crushing failure of Cardiac, Molloy licked his wounds for a spell, doing some design consulting, before a chance encounter hauled him back to hospitality. One afternoon he bumped into Mark Wyborn, part of Viaduct Harbour Holdings, the hugely wealthy collective which owns the Viaduct. “You need Auckland and Auckland needs you,” he told Molloy, and shortly after lent him the money to start his next venture.

Cowboys, like most things with Molloy, wasn’t a hugely sophisticated concept. Staff wore stetsons and customers were encouraged to do the same. Yet sophistication can be the enemy of fun, and Cowboys was another success, the more so when a second location opened in Queenstown. Molloy says he and his then-wife saw the future of the area on a trip down, and immediately set about plans for opening a branch there. The bars powered his recovery from Cardiac, helping finance less successful ventures like Harry’s Place in Parnell. But when his second marriage fell apart, Cowboys was lost, too, and by 2016 Molloy was adrift again.

Wyborn’s group came to the rescue once more, offering Molloy a site on the western corner of the Viaduct that had never before been available. The rent was incredible: free – the only catch being that he had to have it open in time for the Lions tour.

Molloy had Headquarters open six months later, just in time, the pace helped by his giving the tradespeople involved minority stakes (since bought out). After two years it was given a second lease, out to May 2021, this time paying market rent. It now employs 70 people over summer and 50 in winter, and Molloy is often found at the restaurant on the waterside, at a table he likens to a mafia don’s favourite, because it has his back to the wall and a view of the whole operation.

When I first meet him he’s at the next setting over, running a tasting with his GM Kimmi Curtane and two friends he jokingly describes as “hired muscle”. After raging against Bernie Monk, he’s interrupted by yelling from the pavement outside. A man with long hair and an e-bike is remonstrating with him. “They’re throwing me out, mate,” he says. Molloy heads around to the entrance, where the man attempts to gain re-entry. “You don’t know who you’re dealing with,” the man tells Headquarters staff. “I don’t want to stuff up your business.” The scene is half menace, half farce, with tension in the air as the man refuses to leave the entrance. “I couldn’t care less,” Molloy tells the customer. “Now get on your bike and fuck off.”

When I talk to longtime staff about Molloy, the common sentiment is that his willingness to confront situations like that himself is part of what makes them enjoy working for him. “It’s so refreshing to have a business person who does what they say they’re going to do,” says Kilgour. “I’ve worked for a lot of douchebag bosses,” says duty manager Ruben O’Connell. “He’s one of the only ones who really has your back.”

Those close to Molloy frequently see him deploying his will and his temper to causes which require it. Yet the incident with The Project exemplified his dark side. It began innocuously enough, with a patron emailing the restaurant complaining after wind blew confetti from a neighbouring table into the water. The reply dripped with sarcasm. “Clearly it’s something Stevie Wonder would’ve seen but not our bloody brain dead staff”, it read in part, and the tone practically ensured it would become news. It was signed Kimmi Delicious, but clearly authored by Molloy.

Still, it wouldn’t have been a hugely controversial piece – “a boring beat-up of an environmental story”, is how The Project’s Kanoa Lloyd laughingly describes it – were it not for the fury it aroused in him.

Molloy was in Bali at the time, and Project executive producer Jon Bridges says he was initially chatty. “He was charming: ‘hey fella, how are you doing?’,” as Bridges recalls. Then the tone abruptly changed. “People who mess with me, there’s always tears and they’re never mine,” Molloy said, according to Bridges. “Don’t you know who I am? Who my sister is?” Molloy’s sister is TV producer Dame Julie Christie, until recently a board member at MediaWorks, the parent company of Three, The Project’s broadcaster. (Molloy denies mentioning his sister, flatly calling Bridges’ claim “bullshit”.)

His tone in the phone call, parts of which were aired on the show, felt deadly serious, though Molloy claims it was taken out of context and from a conversation he asked to be off the record. The incident didn’t end with the broadcast. Lloyd says she and the segment’s producer received days of abusive text messages from Molloy. “If you get one allegation wrong and damage HQ [Headquarters]… I will pursue all options at my disposal,” he wrote. “And I mean all options.” Another darkly suggested the pair were under surveillance.

He cut short his holiday, and wrote a long social media post under the Headquarters account saying he wished “the parents of Kanoa Lloyd… had used rubber prophylactics”.

She replied to his texts saying, “it’s wild how mad you are about this. Go for a swim, man,” before eventually blocking his number. Lloyd says she was largely unfazed due to strong support around her, but worries for those who might become targets without such networks.

Bridges calls the incident “a bizarre brush with a bizarre character”.

Molloy now says he’s over the episode, but days ago, and more than six weeks after the incident, he sent a text to myself, Lloyd and Bridges, claiming to be “fucking outraged that MediaWorks used a plastic confetti glitter bomb” at the Dancing with the Stars wrap party. “How many fucking turtles died because of this outrage?”

Molloy is a strange figure. “I’m not a typical Kiwi,” he says, accurately, “in the sense that I’m not that shy and I’m not that modest.” He’s manifestly a gifted hospitality operator, capable of taking the raw materials of food and drink and a location and spinning them up into something which draws people in by their thousands.

Yet there’s a lot more to him than that. “He’s a better friend than an enemy,” says Boag ruefully. The flipside of the garrulous host is a man who holds immense, obsessive grudges, even against those who barely know him, like restaurant critic and co-host of The Project Jesse Mulligan, who cannot recall ever meeting him or reviewing his work, and Pasture’s Ed Verner, whose only crime seems to be a business model Molloy thinks foolish.

Molloy’s torrent of opinions, his endless provocations, his seething threats and fury are mostly funny to those who love him. Even if he goes too far at times, they see his lashing out as an acceptable price to pay for all the generous, loyal, driven qualities that are packed into his diminutive frame.

When he wants you to like him, he’s very hard to resist. His mind is sharp, his tolerance low, his vulgarity often charming, his stories extraordinary. In the right light he can seem like a heroic throwback to a New Zealander fast fading: rugged, take-no-prisoners, brawl-and-resolve-it-over-a-beer, able to break bread with everyone from PMs to paupers, more than willing to dish it out and take it.

Yet many of those who have felt his wrath see him in another light. A front runner, combative only on his own terms, willing to do almost anything to win, and unable to see that regardless of his origins and struggles he is now an immensely successful and connected man in his 60s who should know far better. To them he represents another, far less beloved New Zealand archetype: a stunted adolescent and a cruel, pitiless bully.