Acclaimed bestselling author and Good Weekend magazine writer Konrad Marshall, who has written the book(s) on Richmond's recent history, returns to richmondfc.com.au this week for a five-part series celebrating Jack Riewoldt's 300-game milestone.

This morning Konrad continues with Jack according to those who have been on this journey the longest; the Riewoldt family - mother Lesley, father Chris, wife Carly and cousin Nick...

Ask Lesley Riewoldt what her son Jack was like as a child, and her answer is blunt. Brutal even.

“He was annoying,” she says, deadpan at first - then giggling. “You always had to entertain Jack. He was that kid. ‘What are we doing now? Where are we going? When are we going? What’s next?’ Even on wet days we used to have to take him to the squash courts, or else he would drive you insane.”

Jack clearly wasn’t going to sit around on a Saturday with a Playstation for company, says his father, Chris. And so he found sport - anything that involved a ball or bat, running or throwing, and competition. With phys ed teachers for parents, the kid was swiftly furnished with the equipment required to enjoy games of all sorts. “I played golf with him once in a town called Swansea,” says Chris. “We played 9 holes, and he beat me, which is not that hard. But he was six. He was six - and had never played before. He got 54.”

Lesley does the list. Soccer. Cricket. Water polo. Basketball. Indoor cricket. Hockey. Skateboarding. He made up his own little triathlon once, around the block in Hobart. “He wanted to win, too, so he cheated,” Lesley says. “He didn’t put his helmet on, because he didn’t have any time to spare going into the bike leg. The police brought him home, or chased him home. He came racing in the front door and dove under his bed. I couldn’t get him to come out, but eventually he did, and the policeman gave him a stern talking to. Jack was 10.”

There was also an element of something more than competition, but rather self improvement. He became a boundary umpire as a teenager, because it would improve his fitness (and earn him some extra pocket money). He did shot put for a while, too, even placing third in the country at Little Athletics. “He loved it,” says Chris. “Not just because he was competing against other people but competing against himself, improving little by little. If Jack did anything, he did it to be as good as he possibly could.”

This character trait has not dimmed in him either. Riewoldt’s wife Carly sees the same embrace of extra-curricular activities even now, in a life filled enough (surely!) with the duties of professional football, an expanding media presence, and a growing family. She teases her husband, in fact, with the nickname “one hit wonder”, because of his expanding list of pastimes picked up and later dropped.

“You name it, he’s done it - and he doesn’t just try it for a week,” she says. “He buys every gadget and goes for it. Surfing, fishing, university, cycling, building, gardening.” Riewoldt recently got into historical fiction after reading The German Girl by Armando Lucas Correa. “Suddenly he was touting himself as a bookworm! And it’s like, ‘You’re not, but I love that you’re trying’.”

It’s part of what drew her to him in the first place. They’re high school sweethearts, you see, who’ve been together since year 11, when they shared the same health studies and English classes. (They had a deal where he would do her health homework, and she would do his English homework.) Even then he was curious about the world and thoroughly invested in it, whether his stint making screen-print T-shirts, or forming bands, or doing drama. “These hobbies train his brain to learn new skills,” says Carly. “These different states of flow don’t just serve as distractions from football, but add layers. And they’re key to his success. He finds these things and applies himself to them, and gets a different perspective.” 

She loved his dynamism, too.

“I am a person that really worries about what other people think of me, and how I come across, and being polite. But Jack is so unapologetically himself. It’s something I hope we can really pass on to our kids. He stands for what he believes in and is not sorry for that. He’s obviously very vivacious. He was always the loudest in the common room. If it was quiet, it was because Jack was sick and not at school.”

With that in mind, I assume his parents had no qualms about their gregarious boy joining the ranks of the AFL. Chris remembers the year Jack was drafted, and how the team he played for - Clarence - won the premiership. A day or so later, Jack said he wasn’t sure he wanted to leave if he got drafted by an AFL club. “He got a bit emotional,” says Chris, “But it blew over pretty quickly. He was more than ready to go. And excited.”

Once selected by Richmond he initially lived with Tigers tyro Nathan Brown, but quickly moved in with the family of former club board member Rob Dalton. “They really became his second family,” says Chris. “They have three boys just like we have three boys. It was like him being the bigger brother in another family. They took him on like one of theirs, and they’re still his family in Melbourne. It made our worries about him being homesick subside.”

He had family in Melbourne, of course, namely his famous footballing cousin, the St Kilda superstar Nick Riewoldt. “If Jack came to St Kilda, I would have been in a position to provide a lot of help or assistance or support, but once you get into your own club, they’re the ones that really wrap their arms around you,” says Nick. “You’re in the same world, but basically in your own bubbles. There was also a level of ‘Don’t interfere, I’ll find my own way’.”

Nick was confident that Jack could - would - do exactly that. Although they didn’t spend much time together as teenagers (given Nick grew up in Queensland), he implicitly knew that his talented little cuz would be suited to the elite level of the game.

“I knew he would give himself every opportunity, because every single time I ever saw him, he had a footy in his hand,” he says. “The one thing I wondered was ‘Will he be quick enough?’ I probably didn’t have a full appreciation for how agile and powerful he was, when operating in a small area on the field.”

He also had a secret weapon, or rather, a couple of secret weapons. Superstitions, in fact. Footy players are often creatures of habit. Watching the pre-game rituals of players in the rooms below the MCG and you see their habits on full display. Trent Cotchin stands alone, juggling and bouncing and twirling the footy through his legs and around his back, like it has an elastic string. Dylan Grimes does a frenetic footwork drill. On the day before a night game, Kamdyn McIntosh watches cartoons, while Dustin Martin sleeps.

“Jack used to do this thing where he would eat a bag of strawberry and cream lollies before every game,” says Carly. “And he used to wear short socks. I mean he used to actually shorten them, taking them to a seamstress to get them docked. He hated long ones pushed down, or rolled down, or folded down. He got the logo moved and everything. He would spend an insane amount of time and money doing this. But I have a feeling he was always doing these things because he felt like he was supposed to have a quirk.”

He got over that. He realised it doesn’t affect how he plays. “You can have an amazing or atrocious week, and wonder if you ate too many strawberries and creams or too few, or you can figure out things that are meaningful and real,” Carly says. “Now he goes to the Brighton Baths for recovery, because that helps. And the morning before every game, he goes to get a coffee and cupcake with Poppy, because it relaxes him. Those are the worthwhile traditions.”

Naturally, his career hasn’t all been easy. Hub life last year, during the pandemic-affected 2020 season, was much tougher on Riewoldt than he let on - even through his searingly honest public commentary on the disruption. The roughest time, however, was his omission from the club leadership group in 2016. He felt that slight personally, and let it drag him down.

“Jack took that as ‘People don’t like me’, and he felt he wasn’t valued,” Carly says. “And he knew he could bring so much to the table, because leadership is not one straight narrow road. But when he realised it wasn’t personal, and was about trying different perspectives, he totally let that go and realised it’s not about him, it’s about the club and what the group needs as a whole.”

This was, of course, a far more mature Riewoldt than perhaps the public realised. His cousin Maddie had passed away only a year earlier, and with that kind of loss comes an abrupt shift in perspective. “Jack donated a lot of his plasma to Maddie, because he’s a match,” says Carly, softly. “When you’re doing that sort of stuff in the lead up to a game, there’s nothing that compares to that for making you realise how fragile life is. It makes you understand your place in the world,” says Carly. “They’re playing for our entertainment, these guys, and we adore them for it. But they’re not saving lives.” 

Maddie was the same age as Jack, Carly points out - stifling tears - and they were so similar. Her death sheeted home to him how we only have one chance. “I’ll never forget sitting at a game with her - Saints versus Tigers - and if someone at the ground said something about Jack, she was on them, ferociously defending him. And to see her just disintegrate, to say goodbye to someone so young, it was …” her voice trails off. “Nothing could make you grow up more than that.”

Nick believes Jack’s maturation is also somewhat imaginary - that an astute and disciplined and devoted person was always there, if only you looked at him through the right lens. “The same people that were part of that camp who had maligned him for a time, they’re now the same ones saying ‘Oh, look at the maturity! The growth!’ But you could say the same about Cotch, and Dusty - think about the way people speak about them now, compared to before they won their first flag. Success influences perception more than anything.”

Still, there are childish (child like?) episodes Nick loves remembering, such as the time Riewoldt took a spill in a high marking contest, went beneath the MCG for a concussion test, and was then spotted on camera creeping - crawling - up the steps at ground level to the arena, to see what was happening. “For me, that is just such a ‘Young Jack’ moment,” he says. “Equal parts cheekiness with a streak of defiance, but drowned out by enthusiasm.”

He still has that impulsiveness, too. It might leave him open to occasional criticism, but it wins widespread endearment as well. “Last year when all the gyms shut, we did a lot of training together, and with his brothers Charlie and Harry. We started riding bikes, and it was awesome,” Nick says. “But I remember we’d been riding for a month, tops. We’d been on less than 10 rides, and Jack shows up on the best bike available on the market - something that right now would be rolling around in the Tour de France. He had to have that edge. Just couldn’t help himself.”

Jack’s main area of growth, it seems to all the Riewoldts I speak to, is in his ability to communicate - to share himself with confidence and clarity, and compassion, too. “You’ve gotta say that Jack has very much learned that for every action there’s a consequence,” says Lesley. “He’s got so many talents that I think for most of his childhood he could breeze through, but as an adult he realises you’ve gotta put the work in. What else? I think he learned he didn’t have to win games himself - to trust in others and know they’re going to do it better if they do it all together. And I’d say he’s broadened his horizons, and is very accepting of all walks of people. He loves kids - all of my children have been good with little kids.”

Fatherhood has been a blessing and a challenge. If there’s a problem in life generally, Riewoldt wants to fix it, and will talk to as many people as he needs to until he gets to an answer he likes. “But with fatherhood, you don’t always get to be the person who fixes the issue, like when two-year-old Poppy is having a tantrum and only wanting mum, and he has to sit back and let it happen,” Carly says. “It’s taught him patience.”

It’s also taught him new depths of daggy self-deprecation.

“It’s made the qualities we love about him even better - to shine in a different light,” says Carly. “He was dancing at the local cafe this morning because Poppy wanted to dance. You could be really embarrassed - at this guy dancing in a busy shop in Church St, Brighton - or you could be like he was and think ‘Why would I ever say no to dancing with my daughter?’” 

This is a family that runs deep in its connection and devotion. I remember sitting in the Olympic Stand at the MCG in Round 1 of 2018, alongside Chris Riewoldt, wondering how a dad barracks for his son at AFL level. In the first five minutes, I got my answer. A loud Carlton yahoo tore into Jack, mocking some perceived deficiency or another. Chris turned, with a stare you do not want to receive - trust me - and told that Bluebagger to shut the hell up. He tells me now that was actually a rarity. “Lesley is the fierce defender,” he says. “I’m usually pretty passive when I watch the games. Although I do enjoy it when I’m sitting near people and you can hear what they’re saying and it’s something nice. That makes me feel good inside.”

As for 300 games, well, that makes them all feel good inside. Carly sums it up best. After the pain of 2016, they enjoyed the 2017 Grand Final, then they got married, the 2018 season brought a renovation and a baby, then in 2019 another premiership, then another baby, and another flag, and now this amazing milestone.

“I know Jack’s said before that his final goal was always 300 games. And it’s just so wonderful it’s come to that,” she says. “He knows we’re really proud of him. Of course we are. But really we’re just happy he’s happy. It’s the cherry on top of his career. A beautiful career. He couldn’t ask for more than what he’s achieved. It feels like a fairy tale, to be honest.”