Jack Riewoldt speaks to Fox Footy at the 2018 All Australian Awards evening.

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 evening Konrad continues with thoughts from Waleed Aly, Caroline Wilson and Gerard Whateley, who watch in the stands, talk with and about Jack on our screens and in the papers.

Waleed Aly can pinpoint his first Jack Riewoldt memory, but it’s not what you might expect. It was from his debut in 2007, in a Dreamtime game that was memorable mostly for the way Matthew Richardson fumed and seethed, as the win was ripped from his tragic gloved clutches, an infamous free kick instead paid against him. Hands in the back. We all remember that. How could we forget?

But Aly remembers something else, of a skinny young Riewoldt from far earlier in the match - with 37 seconds left to go in the second quarter - and it’s not him flying for a mark or kicking a goal. The shaggy-haired debutant gathers the Sherrin in the right forward pocket at the Ponsford End of the MCG, and gives off a handball to Daniel Jackson, who kicks a low boundary banana to put the Tigers in front. The memory isn’t even really that play, but rather Riewoldt celebrating afterwards, jumping onto his teammate, straddling him in the midst of his first taste of big stage elation.

“What’s weird is that it was so early in his career - literally his debut - but it still felt like ‘signature’ Jack,” says Aly, a lifelong Richmond fan (and one-time Tigers mascot). “I don’t know how that works, but maybe it’s because we’d heard all about him, and he clearly had this swagger in the way that he walked, and carried himself. I remember just being struck immediately by a guy who thought he belonged, even if you didn’t.”

Riewoldt reminded Aly quite a bit of Brett Lee. “It was something about his physicality, or theatrics. You remember how Brett Lee burst onto the scene, five wickets against India at the ‘G?” Aly asks. “There was something immediately exciting about him. Jack felt exciting like that. And excited, too.”

Aly is of course not the only dyed-in-the-wool Tiger tragic in Melbourne media. Trailblazing journalist Caroline Wilson has deep Richmond roots. Jack Riewoldt, she says often, is hands down her favourite player - and not just because he’s such a box office talent. “Everyone loves big marking full forwards, but even in the early years when Richmond didn’t have a lot to cheer about, he was dynamic,” Wilson says. “There have been comparisons to Richo, wearing the heart on the sleeve, sometimes in a negative way, a selfish way, but I actually think he’s the pied piper. I think he’s always been a great leader at the footy club.” 

Wilson recalls, for instance, Riewoldt’s unashamed, stated desire to kick goals, the young player going so far as to talk about being desperate to win the Coleman Medal (which he then did three times). “He was really nervous one year, when Barry Hall might have gone past him in the tally. He said he was almost watching on the TV through blinkered fingers!” she says. “I love that he’s so honest - too many footballers hide their light under a bushel, and they’re too scared to say anything that violates the team ethos. But I think he absolutely loves Richmond, and has never done anything to suggest otherwise.”

And yet, “universally beloved” is not how people would have described mid-career Jack Riewoldt. I wonder if the dislike in certain quarters is a particularly Aussie thing: a stout refusal to lavish any love on lairs. “It is an Australian thing, but we can overlook that if someone has reached a higher station,” Aly reckons. “The problem people had early on is they thought Jack thought he was a big time player, when he hadn’t yet done the big time things. I remember hearing a lot of commentators calling Richmond games, expressing frustration - ‘He’s all about his highlight reel and not doing the team things’ - and I think that narrative took hold a little bit. But what really annoys me about that, is that he went through the most incredible transformation in that regard. He’s one of the least selfish players I’ve ever seen, and it’s almost like no one has noticed. The stuff he does when he’s not kicking goals is out of this world, but the perception of him as someone who only cared about creating highlights hung around well past it’s used by date.”

Wilson well remembers Riewoldt’s most fractious period, which ultimately led him to institute a comically short-lived personal media ban. “He made those supposedly detrimental comments about the coaching - ‘We’re trying to play like Hawthorn’ - and he was right!” she says. “He got attacked for it, but Damien Hardwick was self-deprecating about the whole thing - critical in a humorous way. Then there was that time he tried to run away from the media and got caught at the train station. He was almost prepared to embarrass himself because he felt so strongly.”

A man who has seen Riewoldt as a media performer up close perhaps more than anyone is Gerard Whateley, the host of AFL360 on Fox Footy, who says he was misrepresented early and often. “My view of Jack was that he had ended up in situations where he was presented as something of a clown, and I knew just enough to know that it wasn’t an accurate reflection of who he was.”

22:30

When Whateley sat down with Riewoldt to talk about the high marking forward joining his program for a weekly segment, in place of the retired Bulldog Bob Murphy, he made an offer: If the Jack Riewoldt currently perceived by the public is not who you are, we can provide an environment in which the real you can shine. 

“We collectively had a view that he was tremendously fascinating - a hugely important figure in the game, who hadn’t had a real chance to show who he was,” Whateley says. “We were looking for a player who people thought they knew, but there was clearly more to them. I think Jack was a figure who garnered a level of affection from the way he plays, too. People would have felt like they had an interest in him, almost something at stake.”

Stepping into the shoes vacated by Bob Murphy must have been tricky though. As Aly puts it, Murphy is an extraordinary talent in a media sense - a genuinely lyrical writer, poetic thinker, and artful speaker. “And Jack steps into that, which is really a daunting thing,” Aly says. “I follow a lot of sport, and I’m honestly at the point now where the minute a player is being interviewed I just fast forward, because there’s almost never anything of interest. Even when they’ve done something amazing. But I find Jack great to listen to, and I think what’s happened is that as he’s gotten more comfortable, he’s taken on something of a statesman role. Perhaps because his position in the game is assured, he doesn’t feel the need to hide things? Either way, when they ask him about tribunal controversies, he’ll actually offer a really clear analysis of why he thinks what he thinks. You’re taken into his mind.”

Riewoldt has now proven himself to be a serious performer away from the field, able to talk about the game as if observing it from a distance, whilst also offering the perspective of a participant. He conjures chemistry easily with others, and has a great sense of humour - not always the simplest thing to deploy on air. 

“He is sincere and empathetic, and doesn’t rely on cliches or cheap lines,” Whateley says. “I think he feels he has a contribution to make to the conversation of the game. And if he didn’t make that contribution a thoughtful one, I think he would consider that selling himself short.”

Whateley says he also shows courage in the way he speaks, such as last year, for instance, when describing how players were feeling a level of acute anxiety about what they might face moving into hubs, including what it would do to their families and their own mental wellbeing. “He gave voice to it, and it came at a cost,” Whateley says. “There were former players ready to criticise, but he knew what had to be done and it didn’t come easy. He did that right away, speaking to us from a hotel room just after he had left Melbourne for Sydney, with only a few hours notice. He used the phrase, ‘I don’t know what I’m doing here’.”

As someone who watched AFL360 regularly when Riewoldt joined, I actually suspect his appearances on the program have played a major role in his public renewal. The weekly spot on Players Night became a vehicle for understanding what motivates and drives him - what’s behind every sulky pout or cheshire grin captured under lights by broadcasters.

“That’s the point of that segment,” says Whateley. “The rhythms of the season, and of life, not people just passing through - but to see them in depth, to understand them in depth, their circumstances and the moments that shape who they are. Jack came to us in 2016, which was a terrible season for the Tigers, and since then we’ve shared the journey through three premierships and a Coleman, and all of these things that will see him as a walk-up Hall of Famer. I’m a firm believer that if you are willing, there’s simply no downside to letting the footy community get to know you.”

Wilson suspects the passing of time helped his public image, too, just as it did for Richo, longevity giving people the chance to see him for all his best intentions. “Public sentiment isn’t stupid. There’s a great collective bullshit detector,” Wilson says. “The public could see that Matthew Richardson was a champion football and loyal Tiger, and they can see the same thing about Jack. He’s smart, very clever intellectually, always trying to learn more, and he’s a good person.”

It’s seen him become not just an asset for whatever media company employs him, but also for Richmond. Lately, Riewoldt has become the de facto spokesman for the club when all the most prickly issues arise, because he’s so adept at handling them. “As a speaker he’s like he is as a player - great because he’s interesting, unexpected, and there’s those flashes of brilliance and controversy,” Wilson says. “There’s something so Australian about Jack Riewoldt. He’s the quintessential larrakin, not with drinking and bad behaviour, but with honesty and wit. I love him. And I love seeing him in his twilight.”

I wonder what 300 games means to the likes of those who watch him in the stands, or talk with him - or about him - on screens and in the papers. Aly points out that Richmond fans of his age have never had a premiership side to follow off into the sunset. We have no template for this kind of celebration. These champions of the modern era are now jogging toward the furthest reaches of their careers, but we’ve barely had any retirements or victory laps - milestones like this one are the first step in a long march.

“300 is really where you get to raise the bat,” says Aly. “It invites you to think about how long that journey has been, and in Jack’s case how arduous it’s been. He comes into a Richmond club that is famously tragic. It’s never quite good enough, constantly missing finals in comic circumstances. And he’s taking over from this cult figure in Richo, who never knows a successful team, and Jack’s meant to be the next version of that.

“Then he sees genuinely poor days - he goes from that naively hopeful team to a team in the lower reaches - and sees all of that through to one of the most remarkable football revolutions we’ve seen. He’s such a symbol of what Richmond as a footy club has been through. As 300 approaches, it’s strange. It’s that weird sense of nostalgia, even though he’s not in the past. I can’t wait.”