For Rielly, his troubles started when he tried painting his new house with his fiancé, Tessa Virtue. The couple purchased a historic brick home in Toronto and have since began to paint it white. As the building is a Canadian Heritage home, they required permits to do so, which they got properly. However, City Hall has since ordered them to stop painting the building, citing an error in the permit process.
Leafs fans are largely on Rielly's side in this case, as it does seem rather clear that the couple got the permits necessary to paint the building. It does not sit right with people that the government could just unilaterally force private individuals to stop personal affairs, even when they got the necessary paperwork to do so.
That being said, Rielly's legal troubles are potentially much less worrying that what his teammate and captain John Tavares is currently going through. The City of Toronto is disputing a claim that Tavares received a 15.25 million dollar signing bonus from the Leafs back in 2018. Bonus are taxed differently than regular income, so Tavares could potentially owe the city money.
It is not clear where Tavares stands with the city of Toronto at this point, as details about his possible tax violation have not been revealed. Hopefully though, this will be resolved peacefully, without impacting his on-ice performances next season.