Toronto Maple Leafs star Auston Matthews has become the first active NHLer to sign an endorsement deal with a betting company.

However, as Ontario gears up to open up a regulated sports betting market that would bring revenues back into the province, Matthews’ decision to sign with a grey-market operate may ruffle some feathers.

Per Sports Handle, Matthews has signed with Bet99, a sportsbook in Canada that is not currently licensed to take bets in Ontario. The deal, which is believed to be worth seven figures over three years, will see Matthews promote only Bet99’s free-to-play site in Ontario.

The company’s pay-to-play site is licensed in Canada by the Kahnawá:ke Gaming Commission, a Quebec-based tribal regulating authority. It is currently unknown if Bet99 has applied for an Ontario license to operate.

Matthews joins Canadian UFC fighter Georges St-Pierre as a Bet99 ambassador, and the company is also partnered with the CFL’s Montreal Alouettes and Canadian soccer club CF Montreal.

On Oct. 22, 2021, the National Hockey League Players’ Association had struck a deal with the league that allowed players to pursue advertising and promotional opportunities relating to sportsbooks, under the condition that both single-event betting and those endorsements are legal in the jurisdiction where the betting entity operates.