Jack O ’Grady — Calculated Lunacy / Let’s Talk About Jack

Jack O’Grady, a young man as well-mannered as he is well-travelled. Delivering hard on the promise of his part in Pass~Port’s 2019 video, Kitsch, Jack’s knack for mountainous 50-50s, sprawling downhill lines and a world tour of rugged (and almost comically oversized) flat banks positions his skateboarding as a uniquely rollercoaster affair. Having made an impact in London during the filming of Kitsch, Jack has maintained a connection with the city and travelled further than he ever expected. After turning pro for Pass~Port in 2021, he spent 2022 between his hometown of Sydney, and exploring Europe, whilst beginning to settle into a newfound home of Los Angeles. Catching him, fittingly, on the tail-end of a trip for Geoff Campbell’s ‘Internet Birthday’ series, I spoke to Jack about life so far, his travels, and asked his close friends for some background on the fella they call ‘Squish’.        -Farran Golding

Kickflip in, London. Ph. James Griffiths.

Interview by Farran Golding

How’d you get the nickname, ‘Squish’?
Everyone in my family had chubby cheeks when they were young so, when I was younger, I had a really big face. When I started skating at my local park in Waterloo, I was about 11 or 12 and everyone squeezed my cheeks and earlobes and would say, ‘Gimme some of that squish.’ Then people started calling me ‘Squish Dog’ – that first bit stuck – and now people just call me ‘Squish’. I like it.

I spoke to Matlok [Bennett-Jones], Geoff Campbell and Trent Evans [filmer and Pass~Port owner, respectively] as we were setting this interview up and they spoke about how supportive your parents are. Can you talk about your relationship with them in regards to you and skateboarding?
Right before I [properly] started skating, I was seven and I had played Rugby League since I was five. I had to train on Tuesday and Thursday nights then play on a Saturday. My cousin took me to this indoor skatepark but then I couldn’t go because I had rugby training. One day, when my dad was driving me home from a game, I told him I didn’t want to play anymore because it meant I couldn’t skate. I was only a couple of weeks into skating and I’d played rugby for two years. He took me out [of rugby] straight away and would take me to skateparks.
They’re so supportive of what I do. It’s nice to have that always there. When I was younger, I thought that was normal but growing up I’d speak to friends and realise how lucky I am. Not everyone’s parents are like that. My dad’s always coming to the skatepark or hanging out with the lads. They love it.
Even when I wasn’t doing anything in skating, my parents were backing it. I’d go to comps when I was younger and they’d drive me a couple of hours there, just giving me the option to do what I want to do. Getting older, filming for certain videos and getting on board with Nike at such a young age, it opened my eyes but opened their eyes to see, like, ‘Oh, he can do something here
if he wants to.’ Having footage in Cumberland County [the 2017 Australian Nike SB video], was a big thing for me but for them as well.
The premiere was at Martin Place in Sydney, which was crazy. That was their first premiere, it was my first too, and a lot of people from Sydney and Melbourne were there. They were happy to see the support from everyone. That was the night I got on Pass~Port. We went to this pub after the premiere and they surprised me. Australians riding for international companies is amazing but it was special that Pass~Port, and all they do, is in Australia and especially Sydney. It was nice for my parents to be face-to-face with Trent and for Pass~Port to have a physical presence. That was really special to me as well.

Backside 50-50, Malmö. Ph: Nils Svensson.

You went to Athens with Pass~Port shortly thereafter [Greeced Up, 2018] and Trent said that even then, on your first international trip, you seemed to be in a good place with skating away from home. Why do you think that works for you?
I’m sure a lot of people can agree but it’s that classic thing of having never been there before, and you’ve never seen those spots before, so everything is new and exciting. Skating at home, if there’s a certain spot, you can think about coming back whenever but if you see something when you’re away, you have to do it then or you don’t do it at all. For me, that’s motivating. The majority of trips I go on too are with my good friends and that’s what gets me excited to skate.

The Pass~Port video, Kitsch, felt like a breakout moment for you. Did you see it as that kind of opportunity or were you trying to just do right by those guys?
I was very appreciative to be a part of it. Any chance I got, I was keen to skate and go in. They did a lot of different trips for that and being younger, watching videos – like Alien Workshop’s Mind Field – there are sections where you can tell the team took trips abroad.
It was cool to see that a sponsor takes them to different places to film a part. When Trent said they’re going to do a proper video, taking us here and there, that was like a dream come true.

Frontside heelflip, Maidstone. Ph: James Griffiths.

Some of your standout footage in Kitsch was filmed in London. How far into the video did you come over whilst filming for it?
It was when Carhartt and Pass~Port did this collaboration and video of a trip we took to the Northern Territories [Kiss Me In The NT, 2019]. We came to Europe to premiere that so we went to London, Paris, Brussels and Copenhagen. That was a four-week trip and my first time travelling around Europe. I wanted to stay somewhere longer so I thought I’d pick one [of those cities] and go there.
We went to London first and I met so many people in that week, so I decided to go there again after [the premiere tour]. I stayed at Matlok’s for two weeks, I had a flight home and I cancelled it, booked another for two weeks later, cancelled that, booked another one for three weeks’ time and I might have changed that again.
I think I stayed for a month and a half; at Matlok’s for three or four weeks and then I went to Will Miles’ and Kyron Davis’ house. All of that footage was filmed in that time, going out with Will.

You really went in on a few historic London spots during that trip. Whilst on the other side of the world, Geoff said it was exciting seeing that footage come through. As you’ve been travelling for about as long as you’ve been properly sponsored, do you feel more responsible to produce when you aren’t at home?
Definitely. If someone pays for me to go somewhere and I do fuck all, I feel like a dickhead [laughs]. If someone has organised something, I feel obliged to do my job.

Matlok agreed with me on this but, being English, I’ve always found Australians really easy to get along with. What’s your take on that?
That was one of the main reasons why, having come to London for a week, I wanted to come back and why I stayed for so long. Even today, London is like a second home.
It’s funny, I’ve tried to explain it as well, being Australian and meeting an English person, immediately there’s something in common. Going to other parts of the world sometimes it’s hard to make those connections straight away but with Australian and English people, it’s not like you’re going overboard trying to connect, it’s just a natural thing. So many people I’ve met [in London] are now long-time friends.
I love London, I want to live there at some point for a little bit. Although, I don’t know about the winter. I went recently, when Matlok turned pro, with Trent for a week and a half. We got there three days before the premiere but Matlok didn’t know so Trent and I had to hide for three days. I’ve been around snow before but I’ve never been in a city when it snowed and that was maybe Trent’s second time experiencing it. It was so good. I went to this pub – me, Trent, Will and a few others – then when we came outside it was fully snowing, so powdery. Trent and I were losing our mind, making snow angels probably in this really dirty car park. It’s so cosy, so nice to sit inside whilst it’s snowing but I guess the novelty of it wore off. It was sick for, like, three days then I was like, ‘Ah, it’s actually pretty hard to do stuff here,’ [laughs].

Ollie in, London. Ph. James Griffiths.

As a friend, in his job as the Aussie Nike TM, and through working on videos for Pass~Port, Geoff Campbell has been involved in your life for a long time and in a few different ways. Could you speak more to that?
You’re so right, he’s played a lot of roles. There are a lot of people who have helped me so much, where
I wouldn’t be where I am today without them and Geoff’s one of those people. He’s pushed me a lot whether mentally or physically, he’s bent over backwards for a lot of other people. He’s always putting so much effort in, more effort than he needs to, which is amazing.
On the filming side, I’ve never had a better relationship with someone. I’m sure other people can agree that filming with Geoff is very professional. He’s so passionate about skating and he’s so passionate about filming skating so when you’re with him, he’s very switched on.
It’s funny, someone could do a pretty buck trick and he’ll ask if you can do it again. He’ll ask a skater to do a trick multiple times so he can make the clip as best he can, which I respect. He’s a perfectionist but you can see it when you watch his videos. To me, his filming is insane. When I watch sick fisheye clips, that’s way more exciting than long-lens. Especially coming into it with Geoff, the way he captures something fisheye, a spot could look like shit on a stick and he’d make it really pop. He always makes footage indulging and exciting.

You’ve been living in LA for about a year now. How are you finding it as a base compared to Sydney?
I went there in April of last year, stayed for a month and a half, then I went to Europe for a little over three months and came back to LA but I’d only been there three months before I came back to Australia for Christmas. The last three months was when I got a place so it only feels like I moved there three or four months ago. I can’t fully judge it because I feel like you need to be somewhere for a year before you know what’s going on.
There are good aspects. If you want to go skating every day, you can, which is crazy and why I wanted to move out of Sydney for a little bit. In America and LA, there are so many people whose jobs are in skating, compared to Sydney where a lot of people skate but work as well also. I’m not working a nine-to-five so it can be frustrating if you have to wait until every Saturday to skate with your friends or go filming.
But I miss my friends in Sydney a lot. There are cool people to meet and hang out with but home is where the heart is. Maybe some Australians move to America then that’s them for their whole skating career. I don’t see it like that. It’s just a stop-off. Yeah, but how long is a piece a string? I don’t know how long I’m going live there for but it isn’t going to be a long-long time. As I’ve gotten older, learning about things, skating with my friends is one of the main things that motivates me. I’m meeting and making a lot of cool friends on my travels but you can’t compare anyone to your day-ones, you know? Sydney, I see myself living the rest of my life there but I feel like it’s cool to go places, do your thing, then come back home.

Kickflip, London. Ph. Rafal Wojnowski.

Pass~Port had been gaining momentum for a few years before you were involved but now it’s a really prominent company. Trent does a great job of honing in Aussie, and I guess even local Sydney culture, for the imagery. Do you think Australia was due a company reaching that wider status within skateboarding?
Definitely, and there are other Australian brands, which are amazing, and I’m sure there’s going to be others that take off. You know when you meet someone and then that whole brand just makes sense? That’s what it’s like when you hang out with Trent or you’re talking to him. He’s so open, welcoming and wants to take everything that’s surrounding him and push it out to everyone. I’m lucky to be a part of it and it’s amazing what Trent has done, and what he’s doing, not even just for Pass~Port but for Australian skating.

I guess the likes of Chima [Ferguson] hit a point where he had to go to America to take things further. Whereas with you being younger, coming into a career a couple of generations down the line, skateboarding has a different landscape. The internet gave way for more attention to different locations and some of the companies who were once ‘small brands’ grew thanks to that. Palace, Polar and Pass~Port have been so successful from their home countries and even their home cities. As a result, people have been able to hold down a board sponsor, and often a decent shoe deal, on more of their own terms.
For sure, international skate brands are a big thing all over the world but back in the day you had to be on an American brand to go somewhere. I feel like that’s changed so much. Career-wise, maybe I didn’t have to move to America but I’m at an age where if I wanted to try this, I do it now or I don’t do it at all.It’s good that I got my visa because if I don’t like it, I can go there for a year and if I do like it, I can be there for three years. It’s a comfort. No-one asked me to move to America, there are just certain things I want to do and I think being there will help.
The other side of it, with videos and social media, especially for an Australian, is you don’t necessarily have to move to America. It’s more motivating to see when someone has been successful from their roots, or close to home, and they’ve taken that and shown everyone. Riding for a bigger company and turning pro, that’s amazing as well but it’s cool when people back who backed them from the start or push where they’re from, showing how proud they are of where they’re from.

Ph. James Griffiths.

Trent Evans on Jack O’Grady

Jack was always popping up around the Sydney scene, and I had taken notice, but George Kousoulis – a local videographer, was a big advocate of Jack getting involved with Pass~Port. We surprised him after a Nike video premiere. We made him a cake and a custom bathrobe, threw it on him, and asked if he’d be on the team. Around that time it was a case of getting the blessing from every head on the team, luckily everyone backed him to the nines even before he was even on.
I’m not much of a filmer, only with the 16mm and Super-8, but Geoff [Campbell] took on filming Kitsch and it was a joint venture to edit. When we started stacking up Jack’s footage, we saw it was turning into something special. We were lucky to take the video, and in turn Jack and his part, around the world to premiere it. People sort of lost it for his footage and we used a local band, Low Life. Everything made so much sense to us. It was a punchy edit. We couldn’t be happier with how it all came together and pushed Jack in the right direction as well.
It’s been a good mix at the moment, he’s been back in Sydney for a couple of months and I’ve been going every so often with him. It’s a completely different strategy, I guess, while he’s in Sydney. He’s got unfinished business and new spots pop up. Whereas overseas, I think he thrives even more. If he’s in a country that he may not be back in any time soon and he sees something, he can’t take his mind off that until it’s completed. He will keep going back until he’s landed it or pummelled himself to no return.
He’s very conscious and open minded from his friends to the whole world around him. Squish loves animals and all the innocent things. He was born into a very loving family and you can see that, day to day, always kind and open to anyone he meets. His family has a cupboard of trophies from when he was a kid, a couple of pro boards now as well.
When I’m on tour with him, you see this look in his eye when he’s skating a spot, almost destroying it just by staring at it. The session might go on for an hour or two, this physical trance of sorts, but there’s never any negativity. He’s not throwing his board, he’s inside his mind, battling, then as soon as he lands he’s back to the most stand-up and beautiful human.

Matlok Bennett-Jones on Jack O’Grady

It was my first time in Australia, when we did the Carhartt and Pass~Port trip to the Northern Territory, and I’d seen Greeced Up in Athens so I knew who Squish was. That was where I met him for the first time. Afterwards, I went back to Sydney and stayed at his parent’s house for a while. They looked after me really well and Squish and I spent a lot of time driving around Sydney in his car. We became good friends just from that.
He was amazing then. It was before he was, like, Squish but you could tell. I think people had seen
glimpses but some skaters have ‘the part’ and Kitsch was that for him. It’s nice, those videos where a kid who isn’t as known is who everyone talks about. I was buzzing for him.
When he came to London, filming for all that stuff in Kitsch, I was living in my old place with Jamie Platt and he stayed at ours for a bit. I was working at Slam City at the time and I would go to work, they would come in, and I’d hear about what Squish did that day. It was that situation when someone visits somewhere and there’s all this stuff waiting to be done. Will [Miles] would take him to spots he’d taken us to, which we were wussing out on, or he thought, ‘I’ll see if he’ll skate it’ as a joke, and he just did it all. It was so easy for him. It became a funny thing, taking him everywhere to see if he could fuck a spot up. At the time, I didn’t realise but it’s pretty legendary that he just came to London and did all that.
It’s quite infectious, his view of the world and how he’s a pretty positive person. He never complains about anything. When you’re around him, you want to crack on.

Ph. James Griffiths.

Geoff Campbell on Jack O’Grady

Jack always had big dreams. I feel like he wanted to be a pro skater but something switched, which turned him from being a teenager to being really serious about skating. That’s around the time when there was talk of him getting on Pass~Port. He found his niche and he’s been developing that ever since. Jack, and I’d say this about Nick Boserio as well, they can sell you any trick, you know? The rawness makes it. When he lands and he’s squatting down, clinging on, he could do that on a five-stair and it would look exciting.
As a filmer, you deal with this over time: ‘gnarly skaters’ will say they want to do certain things and you’re, like, ‘Uh, yeah… Are you sure?’ You’re almost worried. You don’t really want to watch it but you have to film it and it’s scary. Jack can switch that to where it seems safe. Everyone thinks he’s a lunatic – and yes he is – but it’s calculated lunacy.
Making Kitsch, Jack lived in Sydney and I’ve always lived in Melbourne. He’d come to stay and film but I often find it frustrating, making videos, when you don’t have access to the people. He went to Europe [in 2019] and I remember getting clips from Will Miles and just being, like, ‘Fuck yes!’ There’s this noseblunt above Southbank coming in, there’s the heelflip over the wall at Stockwell coming in, all of these things. When you’re trying to make a video and ‘sell someone‘ as the gnarly skater they are, you always want more and I was stoked. That trip was a really defining one for him. That stuff’s really valuable – as much as it sounds sort of kooky to say it – but if you go somewhere and do monumental tricks, then people suddenly know who you are.
I have my vision of what parts should look like and Squish is prone to getting a lot of single bangers, hammers or whatever you want to call ‘em. I’m always encouraging him, like, ‘Let’s see you skate a little bit,’ – especially when we talk about his pro part, the solo part [in 2021] – that was a conscious thing of me going to Sydney and being, like, ‘we’re getting lines’. I guess the relationship there is him having his own ideas, giving him my observations, and having mutual respect for each other’s opinions. When you’re editing a video but not filming it, you’re sort of directing it, and when I was waiting for footage to roll in from Orion [Stefandis] it was the same feeling as when he was on that stint in London. He has an awareness of himself, a clear goal. He’s not trying to cop out and get a trick for the sake of getting a trick, he’s going back to spots, aiming high, getting things that people notice. These days, one trick that stands out is almost worth more than a video part. Jack’s trying to do a video part full of those tricks.
He has a really good family and it’s probably part of why he is who he is. He’s a genuine guy with a good upbringing. I’ve always had goings-on with his dad from him being really young to now. Recently, which I thought was cool, his dad reached out to me and was like, ‘Hey, how are you? Jack’s living in the States now and we miss him a lot. How do you think he’s doing?’ His dad has some understanding of what it takes to be a pro skater and I was like, ‘He’s going good.’
Without getting too soppy, over the years, filming with people, being in close quarters and going on trips; inawayIwassoinvolvedinallof this with Jack up until now. He’s moved to the States, he’s left home and it sort of feels like a child leaving – not that I know what that feels like – but I’m proud to say that he’s playing a good role of being a pro skater. He shows maturity in the way he deals with others, which, again, makes me proud because he’s playing out his dream and learning along the way, learning how to do it better.
Back to earlier, when he was young, he’d have these goals like wanting to get the cover of The Skateboarder’s Journal, win Slam‘s Skater of the Year, or get the cover of Thrasher.
Sometimes, I used to think, like, ‘Man, those are pretty big dreams.’ I wouldn’t say I doubted him but I’ve watched him achieve everything he’s claimed, which is pretty cool, but he does it in a classy way. He’s hungry, which I think is a good quality, but he’s got a subtleness about it.

Frontside lipslide from the ledge, London. Ph: James Griffiths.