Richmond utility Daniel Connors has left the club while the Tigers have suspended star midfielder Dustin Martin for two games following a day of drama at Punt Road.
Connors and Martin missed training on Tuesday as a result of both players taking sleeping medication on Monday night.
It is the latest in a long line of indiscretions from Connors, with the most recent incurring a 12-game suspension from the club during the pre-season for alcohol-related issues, meaning the midfielder played his first match of the year in a Round 12 win over GWS, a match where he was one of the Tigers' best players.
That ban followed an eight-game suspension in 2010 for similar behaviour.
A club statement said Connors - who is on prescribed sleeping medication and had not been drinking alcohol - and Richmond had 'mutually agreed to part ways' after he had 'failed to uphold the standards set by the club by missing the training session'.
Richmond-s general manager of football, Craig Cameron, said Connors had failed to meet the club's requirements.
"We have set a standard as a football club and there is a clear expectation that our players meet that standard. Adhering to training requirements is not negotiable," Cameron said.
"Daniel has failed to meet club expectations on a number of occasions and this latest incident can't be considered in isolation.
"Both Richmond Football Club and the AFL Players Association have fully supported Daniel as he has worked through some well-documented issues, and we will continue to work with him while he focuses on his well-being."
Martin, meanwhile, had consumed alcohol on Monday evening, as well as taking a non-prescribed sleeping medication before missing Tuesday's session.
"Dustin understands that missing training is simply unacceptable," Cameron said.
"We want to send a strong message that we don't accept this sort of behaviour and Dustin is now fully aware of this.
"More broadly, our medical staff will continue to educate our entire playing group and emphasise that prescribed medication needs to be taken as directed, and the significant dangers associated with not doing so."