OLLIE WINES remembers flying solo for the first time as vividly as he remembers his first flight to Adelaide as a new AFL draftee. They were a few years apart. But both equally significant. And both equally surreal. Surprisingly, at least for those of us who have never flown a plane, he insists on having felt more in control when he reached for the skies by himself. Not just when it came to the outcome but also about his nerves, and his emotions.
Wines had, of course, completed his mandatory 40 hours of flying under the supervision of his instructor by the time he got the licence to go at it alone. You still see the Port Adelaide superstar's face light up as he recalls that special moment when realised that one of his aviation goals was about to come true.
"To go up and fly a plane solo for the first time without your instructor was one of the most mental experiences I've ever had. You go do a few circuits, which is flying around landing with your instructor, and then they jump out on the tarmac and they say 'off you go' and you've got to be really confident in your skills and capabilities," Wines says.
You can also hear the glee in his voice, as the lifelong "aviation geek" raves about the freedom of flying around the clouds or going as high as he can on a cloudless day.
It's a more mellow tone though that comes through when I ask Wines about that other novel flight experience in December 2012. When as an 18-year-old, he was packed off to Adelaide, a city he'd never visited, as the No.7 draft pick for Port Adelaide, a team he'd never barracked for. And there's an unmistakable rawness in the promptness with which he responds to the query about his first few weeks in an alien city far from his close-knit family in his lovely hometown of Echuca.
"Yeah, I can recall very well. Luckily, I was drafted with one of my best mates, Tom Clurey, who's from Shepparton which is only an hour away. Two days after the draft, we were both put on a plane. And were put up in a hotel in Largs Bay. Danny Butcher used to pick us up and bring us to training each day that first week. I was living with the other drafted boys – Tom, Mason Shaw, Sam Colquhoun and Jake Neade."
Wines would spend nearly a month in Adelaide before Christmas and has a recollection of having packed like a country boy with nothing more than one pair of shoes, one pair of thongs and a pair of runners with a couple of T-shirts. What he still gets emotional talking about though is the homesickness that he battled with in those early days.
"I remember each day after training walking down the jetty on the phone to Mum, saying 'I can't do this, I can't do this'. I think just uprooting your life and moving away at 18, it really shocked me and it took a lot to get used to but I think the amount of phone calls I would have made to Mum and Dad, saying 'I can't do this', and them supporting me and persisting saying 'yes you can, yes you can', probably stands out in my mind."
And the Wines parents were right of course, as their third-born child took remarkably little time to settle into his new home in Port Adelaide. Ask anyone who saw the muscular midfielder in his early days in the Power guernsey, and they talk about how quickly he fitted into the fabric of a Port team that under new coach Ken Hinkley was beginning to redefine itself after a challenging few years. But Wines, who grew up a Carlton supporter, admits having never considered staying longer than the two years for which he was initially contracted.
But here we are, on a sunny autumn afternoon 14 years later, sat across a table from each other in Alberton, at a time when the now 31-year-old is an elder statesman of a young Port outfit which is once again at the beginning of a fresh chapter under a new coach. It's in some ways a full circle moment for Wines, and one he's beginning to acknowledge after having appeared in 280 AFL games for his club.
"They look like a blur to me. There are obviously moments throughout that sort of pin the years but the more I think about it, 14 years, it's a lot of years when you count on your hands," he says.
"That first year, we were a bit of a random bunch of players. We had guys traded in, we had a few drafted, we had some guys that had played for a while so I think just the mix and players we had created a really unique bond and probably from that season I never looked back."
We're three days out from the Power's home game against Carlton at the Adelaide Oval before their mid-season bye. Wines is done with his training session for the day while a number of his teammates are still finishing up either downstairs in the gym or they're milling around in the kitchen not too far from us.
It's not been a great start to the season, at least in terms of results, under Josh Carr for Port Adelaide. But the morale around Alberton is still upbeat after a number of spirited performances in the last few weeks. It's one of the reasons why Wines is feeling more energised than ever before.
"I think I look at myself now at 31 and I'm definitely trying to get different things out of the game as opposed to when I was probably in my early to mid-20s," he says.
"I get so much nourishment these days out of seeing the younger boys like Butters, 'Hornet' (Jason Horne-Francis) and 'Drewy' (Willem Drew) taking those next steps in either their football, their leadership or their development and feeling like I've had a little part to play in that.
"I'm old in footy terms. But the demographic of our group is pretty young, so the energy and creativity they bring has really helped me to stay in tune with that side of the game."
Wines does address the one considerable change that both the club and he personally have had to contend with in the last few months. It's not often a player in the AFL has spent more than a dozen years of his career under his first coach before having to get used to a successor. And while Wines does acknowledge the father-figure role Hinkley played in his life for a majority of his young life, he also credits Carr for the smooth transition that's taken place within the club since the end of the 2025 season.
"I do speak to Ken occasionally and he's got a really good eye for the game, obviously, and gives me any feedback that he thinks I need to hear. But I think 'Carry' has always had great relationships with his players and he's building on that as a senior coach. I've loved everything he's done," he says.
Wines cites two major recent developments that have altered his perspective and, if anything, re-energised his approach towards his footy. He believes the change at the top with Carr taking over is definitely a part of it.
"I only ever had one senior coach, Kenny. Obviously, Josh coming in and having a complete fresh outlook on things, is more change than I've had throughout my career, and I've really enjoyed that," he says.
You can probably get used to the same monotonous schedule and when there's no big change, everything is similar in a way. And I think just having fresh ideas and fresh people in charge has really freshened my outlook up on football."
Wines won't be the first elite athlete in a team environment to appreciate change in this context, even if it's only a case of hearing or learning about the game from a different voice.
"Yeah, it can be as simple as that. I think most 18 AFL clubs are trying to play a similar way," he says.
"The style is a little bit determined by what the AFL is doing with the rules at the time. So, different phrasing, different words, different language around the club is something that can just change up your thinking and challenge you a little bit more and I've enjoyed it."
The other big development in Wines' life is closer to home. He insists that becoming a father has ensured that football is no longer the be- all and end-all in his life.
"Nothing makes me happier than seeing the smile on my son Leo's face. He recognises me as Dad, and he gives me a big smile, and it's imprinted in my mind. It makes me smile," Wines says.
"Leo's enlightened me on when to switch off and know to relax a little bit away from football. He's given me an outlet to not think about it for 24 hours every day."
What hasn't changed one bit is Wines' commitment to his footy and to Port Adelaide. He's still as professional as ever and has maintained his reputation as being a player who sets the highest standards for himself and those around him. And he hasn't yet given up on the ultimate goal of scripting that one major chapter which has remained elusive in his impressive career – that of playing in and winning an AFL Grand Final.
Whatever else he achieves in the rest of his AFL career, Wines will always be celebrated for being the only Port Adelaide player so far to have achieved the ultimate individual accolade in his sport, being one of only 91 players to have won the Brownlow in the span of 102 years. What he refers to has the highlight of his career, but one that he has had to battle with ever since.
"I've probably struggled with a bit of impostor syndrome and perhaps not thinking I'm up to that accolade," he says.
"I still struggle to comprehend it a little bit, seeing the names I'm up against, and my name's on the honour board with them.
"It's been bit more difficult the last couple of years where my body hasn't been at 100 per cent and I haven't been able to physically feel like I can play at that level again, which has been a difficult mental challenge for me to get through, but the Brownlow will be something that I will always reflect back on and think back to that year and one day show Leo."
Wines has seen a number of his peers hang up their boots in recent years, including Charlie Dixon and Travis Boak. He still catches up regularly with some of them, what he refers to as the coffee crew, but hasn't reached that point yet where he starts having discussions with them around his own retirement.
What stands out, though, is the clarity with which he speaks about his post-footy life.
"I think the speed of the game and each year we seem to be adding more game time. I think it's an incredibly physically taxing game and certainly for me, I've had some battles with a knee that are not going to get any worse," he says.
"At the moment, I'm sort of taking it year by year. I'm excited for life after footy. I'm just about to finish a construction management degree and my family business is construction in Melbourne so there's probably going to be a stint there with my brother, Harry, who runs the show there."
The one quality – a virtue, even – that jumps at you when you spend any amount of time talking to Wines about life, is his loyalty.
Loyalty to his roots and his hometown of Echuca, loyalty to his family and the family business, and loyalty to Port Adelaide for what the club has done for him. It's no surprise that he's stuck with the Power for 14 years. And also, no surprise when he insists that this is where he wants to finish his AFL career.
"I don't think it'd be right to finish anywhere else. The club's sacrificed a lot for me. I've sacrificed a lot for the club and it's sort of a two-way street. I really value loyalty, and it was ingrained in me from a young age. I really value the loyalty of our fans and what they do for the football club and what they mean to us," he says.
"Obviously, it sounds biased in me saying (it) but I don't think we've any more passionate fans in the league than ours and what they do for us week in and week out."
When he's not playing footy or tending to his family, Wines is busy indulging in his other sporting passions, whether it's turning up for Old Scotch cricket team to take five-fors with his medium pace or travelling to India to watch Australia in the 50-over World Cup like he did in 2023.
He's also obsessed with American sport and religiously listens to Colin Cowherd's three-hour breakfast show The Herd on Fox Sports. He is fascinated by the business of sport and pays close attention to the legal side of the CBA (Collective Bargaining Agreement) negotiations. In fact, he even spends 15 minutes post our interview inquiring about the possibility of private investment in the Big Bash League (BBL).
It's very endearing to hear Wines talk about Echuca and his family back there. About his mum's amazing cooking, the way he talks about her reiterating that "nothing will change at home. It'll all be the same, as much as you think you're missing out on something", or his indelible love for where he grew up. Even if it's unlikely that he'll ever move back to Echuca, considering the close family connections his partner Olivia has in Adelaide.
Wines still does harbour hopes of fulfilling his childhood dream though of winning the flag in the Goulburn Valley league for Echuca alongside his brother Harry, who's three years younger than him. So much so that he literally jumps out of his seat when I bring it up.
"Did you actually know that (was my dream)? That desire still burns bright and if my body will let me, I really want to play for Echuca with my brother who I've never been able to play footy with and win the flag," he says.
Wines shares his love for aviation, meanwhile, with teammate Mitch Georgiades and has even flown Darcy Byrne-Jones around – though he jokes about not being able to convince DBJ to take on the controls while they were mid-air.
"It was fuelled by my uncle who is a Qantas pilot. Flying is very regimented, and it suits my analytical mind. I like objective results. I like numbers," he says.
"In the air as much as we want to decrease the risk, there's always a little bit of risk so that's probably always suited my lifestyle, and I've always accepted risk and understand you get some really cool experiences on the side. (It's) a lot like playing footy. The instructor's a little bit like your coach taking the training wheels off and knowing that you're safe to go do that."
And going back to flying to finally complete his course, which was interrupted during COVID, and obtain a private licence remains very high on Wines' agenda once his AFL career is over. So that he can tick that other box in his wish list, of piloting a plane back to Echuca. That would in many ways sum up the OIlie Wines story.
The boy from a country town who dreamt of flying high and landed on his feet in a city and a club that's given him everything. But also, a boy from a country town who still dreams of literally flying himself back to where he came from one day.