Tommy started playing blackjack professionally in 1978 while still in college. That was also the year he started his first informal "team." He's never looked back. For more than twenty-five years, he has been running the longest-lasting and most successful blackjack team in the history of the game. He and his teammates have played in casinos all over the U.S., Canada, and the world. He has used big player techniques, concealed computers (when they were legal), and had one of the most successful "ace location" teams ever. He has personally been barred, back-roomed, hand-cuffed, arrested, and even threatened with murder at gun-point by a casino owner he had beaten at the tables. Every year, the Hyland team players take millions of dollars out of the casinos. And even though Tommy has had his name and photo published in the notorious Griffin books more times than any other player in history, he continues to play and beat the games wherever legal blackjack games are offered. He has also fought for players' rights by battling the casinos in the courts.

Despite his fearsome reputation, Tommy is polite, soft-spoken, and always a gentleman. He is as loved by players as he is feared by the casinos. In an interview conducted by Richard Munchkin in 2001, Tommy said, "If someone told me I could make $10 million a year working for a casino, I wouldn't even consider it. It wouldn't take me five minutes to turn it down ... I don't like casinos. I don't like how they ruin people's lives. I don't think the employment they provide is a worthwhile thing for those people. They're taking people that could be contributing to society and making them do a job that has no redeeming social value."