Matt earned VIP status at DraftKings, and his host texted him basically every day to check in, offering bonuses and free tickets to games. He turned down the tickets, since people might wonder how an elementary school teacher could afford amazing seats, and had DraftKings ship various freebies to his school rather than his home. (“I can’t have a package with DraftKings all over it mailed to my house,” he explained. At work, the boxes blended in with all the classroom supplies teachers have delivered nowadays.) Not once, Matt said, did DraftKings ask what he did for a living, whether he could afford to gamble so much, or whether he had a problem, even as he aggressively ramped up how much and how often he was betting. “I had no business doing that. So, why didn’t someone question where is this guy getting this money? And is there something else going on? But to them, it’s just money in their machine.” DraftKings declined to comment. Brian Hatch, who served as Matt’s addiction counselor in Connecticut, …