Richmond coach Damien Hardwick is "uncomfortable" with the situation but remains confident emerging star Shai Bolton will shun interest from rival clubs to remain with the AFL powerhouse beyond this season.
Bolton is out of contract at the end of 2021 and his manager Ralph Carr has repeatedly stated his client is in no rush to sign a new deal.
The 22-year-old finished fourth in the Tigers' best-and-fairest last season and claimed his second premiership medal.
"I'm always uncomfortable with good players out of contract, but we love Shai and I'm pretty sure he loves us as well," Hardwick said on Wednesday. "That'll just take a bit of time to work through.
"These contract discussions are always like that, but we're very confident in what we've created here (and) that players want to stay and players want to come."
Richmond saw Jack Higgins and Oleg Markov take up strong offers from rival clubs at the end of last season, while premiership pair Dan Butler and Brandon Ellis made similar moves a year earlier.
Hardwick said he doesn't begrudge players "looking at different situations that might afford them some luxuries in life".
But he said the Tigers had developed a strong culture that entices players to sign for less money than they could earn elsewhere in order to stay at Punt Road.
"It's the thing you give up to stay at a successful club," Hardwick said. "We've seen that over a number of years at other clubs that have been really successful; Hawthorn and Geelong in modern times.
"If you want success you've got to give up something and generally it's monetary."
Bolton averages a career-best 22 disposals and a goal per game in 2021 and will be important to Richmond's chances of beating Geelong in Friday night's blockbuster clash.
The Tigers have lost Dylan Grimes and captain Trent Cotchin to injury, but Hardwick confirmed Nick Vlastuin and superstar Dustin Martin will return against the Cats.