Jeff Jackson watched as money and opportunities from legalized sports wagering poured into the NHL. The League was banking deals with sportsbooks. The teams were creating formal relationships with gambling partners, in some cases even carving out real estate inside arenas for them.

Jackson, an NHLPA certified agent and EVP with Wasserman Hockey, wondered: Why not the players?

Earlier this month, BetMGM announced that Edmonton Oilers star Connor McDavid would join Wayne Gretzky and Kevin Garnett among its brand ambassadors. He's the first active professional athlete from the four major sports to sign with BetMGM.

"It's a growing business. The NHL and teams are doing deals. Why wouldn't we look at it?" said Jackson, who represents McDavid. "The players are going to do these deals. If we're comfortable doing it, and Connor was, why wouldn't we be out there before everyone else?"

McDavid was one of two superstars to get out early on the endorsement front. Last month, Toronto Maple Leafs star Auston Matthews announced his partnership with Bet99, a Canadian sportsbook and online casino. Matthews's deal, to start, only includes promotion of Bet99's free-to-play site.

"I think Auston's proven throughout his career that he is open minded and wiling to explore different opportunities," said his agent, Judd Moldaver, EVP for Wasserman Hockey

Active NHL players promoting wagering sites would have been inconceivable a few years ago. Obviously, the legalization of single-game sports wagering around North American changed that in a hurry. But it wasn't until last October that the NHLPA and the NHL struck a deal to allow players to participate in endorsement deals and promotional involvement with the sportsbooks.

"Once the Players Association and the NHL came to their agreement that the players were going to be allowed to move into that space, we just started looking at it. There was opportunity there to do a cool deal," said Jackson.

There are some parameters that the players had to follow.