Most of them bet on the Eagles to win the Super Bowl or the Celtics to win it all this year. They were in good company – joined by former Boston sports icons like Johnny Damon, Matt Light, Ty Law, Shawn Thornton, Eddie House and Cedric Maxwell – just to name a few. NBC Sports Boston's Tom Giles provides an explainer to the start of in-person sports betting in Massachusetts.Īt Encore, the main event was at the WynnBET Sportsbook Windows – where at 10 a.m., 32 lucky guests were chosen to place some of the first legal sports bets in Massachusetts.