Jack O'Grady takes out New Gen of the Year! The young gun from the Shire has his foot on the accelerator and he’s not slowing down. Squish smashed it in 2017 and over the past year he had footage in Cumberland County, landed a spot on Pass~Port and had two magazine covers!
Kick back and enjoy Jack’s New Gen Interview from issue 215.
Portrait: Sam Coady.
Slappy nosegrind. Photo by Jason Morey.
So you just scored a place on the Pass~Port team, how does it feel?
I still feel like I’m in a dream. I can’t believe it. I’m over the moon. I woke up on the Sunday morning after the premiere still in shock! I’m really excited for what the future holds.
Tell us about the surprise at the Cumberland County after party.
I had no idea it was happening. We were at The Cricketers Arms and my good friend Zoolz [George Kousoulis] kept wanting me to stay upstairs. I wanted to socialise downstairs, but then someone said that the Nike guys had to get a photo upstairs, so I went up there. I went to the bar and Wade Burkitt approached me and asked if I wanted to ride for Amnesia Skateboards. I didn’t really want to and didn’t know what to say.
Then Middsy [Chris Middlebrook] grabbed me and said, “Come in the other room for a photo.” I walked in and everyone was in there with all my family and friends screaming and shouting. There was a beautiful chocolate cake with my dumb head on it, plus my name and Pass~Port written with icing. Trent [Evans] was standing there with a Pass~Port robe that he placed on me [laughs]. Then he said, “Welcome to the team.” I actually couldn’t believe it. The first thing I said to Trent was, “Are you sure?” I was speechless and on cloud nine; it was so cool how they surprised me. I can’t thank them enough.
There’s some footage of you skating outside the Cricketers in your Pass~Port bathrobe the next day, then you went back into the bar. Was the party still going at that point?
[Laughs] Nah, I was actually skating a spot right near the Cricketers with Scoady [Sam Coady] and George. On the night of the prem I accidentally left the Pass~Port robe there and was spewing the next day because I wanted it so bad. I was 100 per cent sure someone would have taken it, but I asked behind the bar and there it was. So then we filmed that little video with George.
Cumberland County was full of bangers. Which trick did you work the hardest for?
I think it might have been the ollie down then tré flip at the two sets in a row, right next to Supply. I think it took me pretty close to two hours to get it. It was just hard to have my feet set up for the tré straight after the ollie, but somehow I rolled away from it. I landed one before the proper land but I ran into the telegraph pole at the bottom. I ate heaps of shit, but I really wanted to do it properly [laughs]. Ceelo-Steelo [Connal Lo] put $50 on that try and my good friend Clarkey [Michael Clarke] put $20 on it as well. I got lucky and my pockets were a little heavier when I left [laughs].
Ollie down to quick feet on a 360 flip. Photo by Sam Coady.
Cumberland County was also a tight edit, do you have footage that you’re saving for something else?
Everyone in Cumberland County absolutely smashed it, no doubt about that! They all worked so hard and you can obviously see that it paid off in the end. Nike is coming out with a new video at the end of next year and so is Pass~Port, so I’m gonna do my best and get as much stuff as I can for both. George and the rest of the Lodown crew are also working on a web clip, which is coming very soon, so I’m gonna try get some stuff for that as well.
You’re still 17 and yet you were able to get into the Cricketers for the after party – tell us about your fake ID.
My good friend Jack Paterson had one for a while before he was 18 and it worked everywhere, so I ordered this European driver’s licence from the same website he got his from. I put all my details, including a mug shot of myself and a 50-dollar-note, in an envelope and sent it off to the UK. A month later the little puppy rocked up at my doorstep in a blank envelope with nothing but my details and the ID.
Does it seriously say Dilly T on it?
[Laughs] Almost. It says Dylan Taylor, which is the name I chose. From that, people started calling me Dilly T and DT. I’m pretty sure Geoff Campbell was the one who started the nicknames.
And you’re still in high school, how’s that going?
Yeah, I’m in year 12 at the moment. It’s pretty fun going to school every day and seeing my friends. I miss a bit of school to skate, which is pretty good. I’m doing a non-ATAR path, so most of the time it’s not that hard, compared to other people doing ATAR.
Frontside Smith grind to ollie out over the bench. Photo by Sam Coady.
What are your plans when you finish?
I get asked a lot about what I want to do when I finish, but I’m still really unsure what I want to do. I know I really want to skate, but who knows what’s going to happen? I’m not too keen on getting a trade.
So you clean pools for a job. Is that a pretty sweet gig?
Yeah, I do that three days a week after school. It’s actually the best job I’ve ever had. I go to people’s houses and give their pools a service and a clean, often at really big houses because I work in the rich part of my area. My good friend Horps [Brad Harper] got me the job there, which I’m very appreciative of. I love dogs, and I get to see heaps of nice pooches every single day; as you can imagine, rich people have the best dogs.
Have you had any sexy mums scoping the pool boy?
If I’m lucky. I get to see some good looking housewives, mums and golddiggers, which is always good. One house that I work at has a really good mini and the guy lets us skate it when we work.
Apparently, you just got your P’s, congrats. Do you have a car?
Thank you, and yes I do, it’s a red and silver Subaru Outback 2001 model. The Outback never disappoints. I love driving; you never get bored, you always have something to do because you’re not stuck at home all the time.
Ollie over to body varial. Sequence: Sam Coady.
Did you really get your first lap dance at 14?
That is correct. I was on a trip to Canberra filming for Treat Yourself with all the Lodown Skateshop lads. One night we stayed at this place with cabins, which coincidentally was the same place I stayed at during my year 6 school camp to Canberra. Anyway, we were back at the room after a long day of skating. Everyone was pretty pissed and someone ordered a stripper. As she pulled up in her Holden Commodore, I hid in the corner with a hoodie on and then watched her do what she does best. At the end, she goes, “All right, last dance,” and everyone goes, “Yeah, Squish, get up there,” so I did. She was off it at first but then my good friend Pup [Tom Ackroyd] gave her an extra $50 and told her I was 16. She said, “Oh, I’ve done a few 16-year-olds in my time,” and then gave me a lap dance [laughs]. I was trying to keep it together after four beers or something [laughs]. So I got my first lap dance in the same cabin I stayed in for year 6 camp.
Who gave you the nickname ‘Squish’ and why?
It was Eddy Lovell, an old friend that I used to skate with back in the day. I was the chubbiest kid and had massive cheeks and earlobes. Everyone would come up to me at Waterloo and grab my cheeks and earlobes and say, “Give me some of that squish” [laughs]. So one day Eddy just started calling me Squish and I guess it stuck.
Is it true that a dog bit you on the face when you were three years old?
I think I was four or five and I remember it only vaguely. It was our pet dog – a German shepherd – whose name was Micky. She was a really good dog, but I was a dumb baby, so I grabbed the bone out of her mouth when she was chewing on it in the backyard. She bit me on the face really badly, right next to my eye. I didn’t have to get stitches or go to the hospital, but it was pretty bad. I did take her bone, though; if I was the dog I probably would have bitten me, too [laughs].
Have you always lived in The Shire?
Yeah, I am born and bred in God’s Country, also known as The Shire. It’s good living here in the ’burbs; it’s about a 40-minute drive from the city. All my friends live really close and it’s a nice scenic place. It’s even more scenic now with Cronulla skatepark just five minutes from my house. That puts the icing on the cake.
Ollieing out of a long 50-50. Photo by Jason Morey.
Your family was at the Cumberland County premiere and the after party and they seemed pretty proud. Have they generally been supportive of your skating?
Yeah, they were all there on the night of the premiere, which was so cool. My old man was definitely having a ball – he didn’t leave the bar with everyone until about 4am [laughs]. My whole family is really supportive of my skating, especially my parents. They’d do anything to help me with skating. They’re really interested in it, which I really appreciate.
George Kousoulis has looked after you a lot, was he your skate guardian when you were younger?
George has been mistaken numerous times for my uncle, brother and even my dad [laughs]. He used to drive me everywhere because he lives heaps close to me. He would pick me up and drop me home all the time. It feels good now that I’ve got my licence and I can return the favour. I looked up to George so much when I was younger and I still do to this day. He has influenced me in skating and in life. He has taught me a lot of things and I wouldn’t be where I am today if it wasn’t for him. I can’t wait to create some more classic memories with him in the future.
Is it sometimes hard being the youngest kid in the crew?
Nah, it’s pretty fun. You cop shit sometimes but it’s all fun and games. I’m the youngest of four in my family so I’m pretty used to it. On a trip to Tassie I copped it pretty hard, though; one night the guys put me inside my suitcase and zipped it up and I couldn’t move [laughs]. At the end of the trip I was contemplating whether these guys were still my friends or not [laughs], but nah, it’s all fun and games.
And what’s the grand plan for you, O’Grady?
Not too sure what the plan is yet, to be honest; I’ve got a few ideas, but I’m just gonna have fun with it and see where the wind takes me.