Caddy, who arrived in 2016 in what has been one of the best trade windows in Richmond history, only featured six times for Damien Hardwick's side in 2021 and has been out of favour for the last couple of seasons.
According to The Herald Sun, the wingman is exploring his options and has an understanding with the club that they wouldn't stand in his way if he wishes to leave, despite him having a year left on his contract.
There is reportedly one interstate club that are interested in his services, with the side in question likely having to throw in a late pick to secure the 28-year-old's services.
Caddy's situation is one on a sizeable list of players whose future is uncertain at Punt Road beyond 2021.
The dilemma over Callum Coleman-Jones and Mabior Chol's contracts have troubled the club in recent times, with the general view being that Coleman-Jones is the preferred tall despite Chol having a catalogue of promising displays.
Shane Edwards too is another high-profile name that hasn't put pen to paper on a deal past 2021, with the quick-handed midfielder out-of-contract at the end of this year.
However it isn't to say that the Tigers have stayed stagnant on contracts with other players in 2021, with most of the off-contract stars coming into this year already signed on.
Jack Riewoldt penned a single-year deal as he looks to hang up his in the next few years, while earlier today Daniel Rioli and Rhyan Mansell signed new deals with the club.
With the Tigers finishing in ninth in what was an injury-ravaged season for the side, Hardwick and co. will be hoping to get back to winning ways in season 2022.