JACK Riewoldt can never be accused of doing things by halves.

Friday night will mark Riewoldt's 300th game, when he will join fellow club greats Kevin Bartlett (403 games), Jack Dyer (311) and Francis Bourke (300) in rarefied Tiger air.

His journey from pick No.13 in the 2006 NAB AFL Draft (selected from the Tassie Mariners) to a three-time Coleman medallist and premiership player has been anything but straightforward.

Following directly in the footsteps of a club's most beloved figure is tough. Riewoldt arrived at Richmond just as Matthew Richardson's career was ending. For so long, 'Richo' had been the beacon of hope for the downtrodden faithful, and they were desperate to anoint an heir.

Was this scrawny kid, standing at just 193cm and bearing a famous footy name, the next yellow and black saviour?

Not only did Riewoldt bear the weight of Richmond's next great hope, he carried a surname synonymous with one of the hardest working forwards the game has seen.

The comparisons to his cousin, 'Saint Nick', have never left but they now extend to include Jack's three flags and Coleman medals versus Nick's aerial heroics, power running and elite work ethic.

He's one of the few survivors from the Terry Wallace era. Riewoldt arrived at the club alongside good mate Shane Edwards, with Trent Cotchin the only other current Tiger to have played under Wallace's tenure that ended midway through the 2009 season.

The early days were grim.

Riewoldt had just a 35 per cent win rate in his first 100 games, as the club finished last in his debut season of 2007, ninth in 2008, 15th in 2009 and again in 2010, Damien Hardwick's first in charge.

"It's one of the things I'm really proud about, I've actually experienced the real lows of AFL football and finishing last and getting early draft picks, the hype of players coming in," Riewoldt told reporters at a media conference ahead of his milestone game. 

"To see success, it's the journey and the way I would have loved to have done it."

Hardwick's first two months in charge were agony. The Tigers didn't win a game under their new coach until round 10 in the pouring rain against Port Adelaide.

During that barren streak, Riewoldt was a desperately needed beacon of hope.

In the absence of team success, the rising young spearhead just kept kicking goals with his dangerous combination of athleticism and footy smarts.

A fortnight after the breakthrough win against the Power, the Tiger Army could feel something in the air a fortnight later on a brisk winter's day at the MCG as Riewoldt ran riot with a 10-goal haul against West Coast.

It was hope.

Riewoldt won his first Coleman Medal that year, aged just 21, and saluted again in 2012.

His flair on the field often extended to his antics off it.

He famously crawled back up the player's race after suffering a concussion in round two, 2011 against St Kilda, trying to get Hardwick's attention to allow him back onto the field.

The coach and medical staff wisely refused.

And no reflection on Riewoldt is complete without mention of Richmond Railway Station.

With the team battling for form in 2014, Riewoldt was publicly critical of a new, short-kicking game style Hardwick had asked his players to employ.

The next day, following a dressing down from his unimpressed coach, Riewoldt was keen to avoid the media pack waiting for him after training. He thought his best bet was to leave his car in the Punt Road Oval car park for another time, jump a fence and run across to Richmond station.

The cameras only caught up with him because he needed to buy a ticket.

It's often forgotten amid the controversy that Riewoldt proceeded to boot a career-best haul of 11.2 against GWS that weekend.

Fast-forward to 2021, and Riewoldt is a considered media performer, often deferred to as one of the voices of AFL's playing group and something of an elder statesman.

It was Riewoldt the club put up for the first press conference following news of Hardwick's marriage break-up earlier this year, and his opinions from his regular spot on Fox Footy's AFL 360 often make headlines.

One of the most impressive aspects of Riewoldt's career has been his progression from having to be the star to being almost too unselfish.

It's mirrored Richmond's rise and changing game plan, and a natural personal maturation over the past 15 years.

In early 2017, Ben Griffiths' absence and eventual retirement with concussion issues forced Hardwick into a reshuffle of the attack. With a lack of other tall options, Riewoldt became the sole focal point with a group of raw small forwards around him.

It ushered in a new era for the canny spearhead, the new game style suiting his footy brain and instincts.

Tap-ons, excellent vision, pin-point passes and crashing packs to allow Daniel Rioli, Jason Castagna, Dan Butler and Jacob Townsend to feast on ground ball became hallmarks of his game, and his leadership was key in Richmond's unlikely charge to the 2017 premiership.

"He's the most naturally talented footballer I've seen, and that includes Dustin (Martin)," Shane Edwards told richmondfc.com.au.

"I say that because Jack has almost single-handedly kicked us enough goals over more than a decade to keep us competitive.

"And he's always playing on someone taller and quicker. And for a long time, he wasn't on the end of great delivery. He would do it using tricks and smarts and nous, turning his man inside out."

The 2017 flag culminated in a celebration that perfectly encapsulated the incredulity of the drought-breaking win – Riewoldt, still in that striking, predominantly yellow guernsey with a scarcely believable premiership medal around his neck, bellowing out Mr Brightside alongside The Killers in the middle of the MCG.

As the great players do, Riewoldt has a knack of making an impact on the game at precisely the right moment. There's been many a fourth quarter in Richmond's recent success which has started with Riewoldt taking a powerful mark and embracing the responsibility to convert.

"From 2016 to 2018, there's been a lot of things happen in my life. The passing of my cousin Maddie was a really trying time for my family and myself, I got married and had our first child Poppy," Riewoldt said on Wednesday. 

"They were really pivotal times in my life, and the journey of a footballer is you see the person in a jumper every weekend, but you never see the crucial path behind the young man or girl who plays AFL and what goes into that."

Tiger fans love Riewoldt dearly. To them, he's simply 'Jack'.

Opposition fans are often, let's say, not fans.

But it's unlikely he'd have it any other way.