Riewoldt was taken at pick 13 of the 2006 National Draft and has since installed himself as a legend at the club, kicking 785 goals over his 17-year tenure at Punt Road.
He has also played the second most games for Richmond, sitting only behind Kevin Bartlett. Riewoldt has built an impressive resume over his career, claiming two best and fairests, three All-Australian selections, three Coleman Medals and has been the club's leading goalkicker in 11 seasons, with 2023 potentially being another.
"There's still discussions between more so me, and Trent (Cotchin) he is in the same boat as me, and Blair Hartley the list manager and one of our football managers, and we just constantly chat and keep each other informed because there's days where you go 'nah, oh yeah' changing our mind every ten minutes," Riewoldt said.
"You just have to be honest but also that the other thing is that like last year, we are probably the last priority if we do want to play on because it's 'here's what's left'.
"That's what we pay you, because I'm 34 and Trent is 33. There are other priorities in football like re-signing and making sure we can get the best out of the club in the next decade rather than the next ten minutes, so we continue to have conversations ."
Riewoldt was quizzed as to whether he had another season left in the tank, but responded to the question with the intention that it will be decided on how he, physically and mentally, feels.
"I don't know, there's three games to decide. I don't think they will decide (performance-wise) but it's just how I feel," he added.
Riewoldt signed a one-year deal in September 2022, taking a pay cut to build the future at Richmond, joining Trent Cotchin, who signed his last contract extension late last year, to face a near imminent call to retire come this season's end.
Another factor on whether Riewoldt will stay may depend on the situations around his former coach, Damien Hardwick and teammate Dustin Martin, who has speculation surrounding him on moving interstate once again.
However, on Wednesday morning, according to the Herald Sun, Martin is reportedly open to playing for Richmond past the end of his contract next season and potentially for multiple years after 2024.
Whilst talks between him and the club are yet to happen, it is understood he intends to extend.