MELBOURNE, AUSTRALIA - APRIL 24: Tigers head coach Damien Hardwick (L) Jack Riewoldt of the Tigers (C) and Tom Lynch of the Tigers stand in line for a minutes silence during the ANZAC observance during the round 6 AFL match between Richmond and Melbourne at Melbourne Cricket Ground on April 24, 2019 in Melbourne, Australia. (Photo by Michael Dodge/Getty Images)

"I don't know," Jack Riewoldt answered.

"I've probably changed my mind three times on the way in the car."

To play on, or not to play on, that is the question. And whether the 34-year-old has an answer with less than a month to go in his 17th season as a Tiger, he wasn't willing to share it on Tuesday night.

Since being selected with the 13th pick of the 2006 AFL Draft, moving north from Clarence to partner Devonport's favourite son, Matthew Richardson, Riewoldt has evolved from a redheaded kid with potential to an undisputed champion of the Richmond Football club.

345 games, and counting. 785 goals, ditto. Three flags, three Colemans, three All-Australian blazers. A pair of club champion gongs and 11 goalkicking titles - second only to Richo - Riewoldt has flipped just about every stone; often with resounding success.

Yet without a deal to remain at Punt Road beyond the end of the 2023 season - a campaign in which the veteran spearhead has featured on 19 of a possible 20 occasions - Riewoldt is at a three-pronged fork in the road.

Does the forward stay on to bow out a one-club player?

Does he link up with an old mate up north?

Or, does he buy time before making a homecoming?

With plenty to unpack, or pack up as the future may prove, we run the rule over the doors faced by the inimitable Tiger.

Yellow and back

For almost the entirety of his AFL career, the thought of Riewoldt wearing anything other than a yellow and black guernsey had been laughable. It still is if you ask one-eyed Tiges.

Yet, without a contract to continue on, the potential for a brand new coach in 2024 and ambiguity surrounding just how long the spearhead can be expected to partner Tom Lynch properly, there are many questions but only three answers: call it quits, stay a one-club player or try something new at age 35.

AFL Rd 8 - GWS v Richmond
SYDNEY, AUSTRALIA - JULY 24: Jack Riewoldt of the Tigers looks on during the round 8 AFL match between the Greater Western Sydney Giants and the Richmond Tigers at GIANTS Stadium on July 24, 2020 in Sydney, Australia. (Photo by Ryan Pierse/Getty Images)

There is no doubt that the veteran has earned the right to make his own call, with Richmond's brass sure to back him either way. But if there is to be a new era at Punt Road under head coach No.39, in opposition to Riewoldt at the minute, the selectors and list managers will likely have their preference.

And whether it is that Riewoldt opts to head to a second home, focus on his fledgling media career or, perhaps, both, real options are available to him.

Season in the sun

If we are led to believe the utterly believable, Damien Hardwick will be the fourth full-time coach of the Gold Coast Suns.

When exactly Hardwick is expected to sign on the dotted line is still up for debate, yet, what is known is that when the triple premiership coach arrives at Carrara, he will be met by a couple of familiar faces in former Tigers Mabior Chol and Brandon Ellis.

Though unable to pull the trigger just yet, Hardwick will also be faced with a chin scratcher of his own: offer Levi Casboult an extension or move Riewoldt north to act as Ben King's mentor.

On paper, it is straightforward. However, in practice, the sale of sunshine and superannuation top-up isn't as black and white.

MELBOURNE, AUSTRALIA - JULY 18: Jack Riewoldt of the Tigers listens to Tigers head coach Damien Hardwick during a Richmond Tigers AFL training session at Punt Road Oval on July 18, 2019 in Melbourne, Australia. (Photo by Michael Dodge/Getty Images)

If Riewoldt harbours a desire to coach after hanging up the boots, shifting his young family to the Sunshine State to do his apprenticeship under his own mentor makes total sense. And as proven by Luke Hodge and Alastair Lynch, living north of the Tweed is no impediment to winning, and keeping, a broadcasting role, so there are at least two irons in the fire.

Throw in the fact that Riewoldt's cousin, former St Kilda skipper Nick Riewoldt, called the Glitter Strip home between ages nine and 18, and at least the legendary Tiger will have a read on the real estate market.

Career, club or the call of his former coach? Riewoldt certainly has plenty to think about before any trade between Cremorne and Carrara becomes reality.

Homeward bound

Punt Road may have become home for Riewoldt since arriving in late 2006, however, there is nothing like the feeling of actually going home.

Born in Hobart and cutting his teeth in the TSL for Clarence, Riewoldt is a proud Tasmanian, having routinely spoken throughout his career about his desire to see a team from the Apple Isle in the AFL.

But with the spearhead set to be nearing 40 by the time the league's 19th team makes its inaugural appearance in 2028, a job in the coaches box appears about the only way Jack can join in

HOBART, AUSTRALIA - MAY 03: (L-R) Tasmanian Premier Jeremy Rockliff, Gillon McLachlan, Chief Executive Officer of the AFL and Deputy PM Richard Marles chat during the AFL Tasmanian Team Announcement at North Hobart Oval on May 03, 2023 in Hobart, Australia. (Photo by Michael Willson/AFL Photos via Getty Images)

Despite being granted an AFL licence in May, plenty of ambiguity still surrounds the Tassie team, with colours, mascots, players, coaches and, most contentiously, stadiums still to be decided upon.

With at least four full seasons up his sleeves to wrap up as a player and earn some stripes as a line coach, if Riewoldt has eyes on leading the Map against the mainlanders, his path forward has become clear.

And even if a role working in footy's fourth estate is his calling, given his gold-leafed credentials, a part-time consulting role supplementing his growing media presence could well arise for Riewoldt.

Up forward in a yellow sash, moving magnets with an old mate or calling the shots in the commentary box, the choice is Jack's, and wife Carly's, to make.