Tommy Hyland

Tommy Hyland is one of the most famous professional blackjack players of all time. Having initiated the longest-running—and immensely successful—blackjack card counting team in the history of the game, Hyland was among the very first inductees of the Blackjack Hall of Fame in its debut year, 2002.

Pitching Pennies to Tossing Chips

Tommy Hyland, from Pitching Pennies to Bankrolling Thousands in BlackjackBorn in 1956, Tommy Hyland grew up in New Jersey where, like many professional bettors, he learned to gamble at a very young age. While in the fifth grade, he and his friends played a game known as Pitching Pennies. Each player would toss a coin against a wall, and the player whose coin landed closest to the wall would collect all of the coins in play.

It wasn’t long before Hyland began sports betting, but not on other teams – on himself. Tommy was a fantastic athlete who participated in multiple sports growing up, including baseball, basketball and golf, among others. He was betting a dollar, or a soda, on rounds of golf before he became a teenager; a wagering activity he learned from his father, a recreational gambler who only bet small amounts on rare occasions.

Once Tommy reached high school, his sports betting had become so widespread that he actually backed his own pool cards for awhile, becoming the house rather than the player; an activity he’s not so proud of in his mature years.

It wasn’t until Hyland attended college in Ohio that he really became diluted with gambling activities. He was still betting on golf—for much more money than before—but also began playing poker. Tommy once described himself during his college years as a “bum”, neglecting studies to read up on gambling strategies.

Tommy’s life would take a whole new path when he picked up a copy of the 1971 book, ‘Playing Blackjack As A Business’, by Lawrence Revere. With the help of his roommate, Hyland began studying strategies in-depth in 1978, and living fairly close to Atlantic gave him plenty of opportunities to test his new skills.

Hyland admitted that it took him a long time to master the art of card counting. Although many of the books he read taught the practice, he said it was never explained properly. In order master the skill, he and another friend would spend hours dealing cards and keeping counts until they finally became good enough at it, but only when working as a team.

While playing at Resorts Casino, Hyland met another future Hall of Famer, Stanford Wong, author of ‘Professional Blackjack’, who immediately recognized the two were trying to count cards. Wong gave them some tips that Tommy utilized to perfect their strategy, and before long, they met several other card counting experts. Under the guidance of Ken Uston’s book, ‘Million Dollar Blackjack’, which spoke about forming teams, Hyland established what would become the longest running blackjack team in history.

Hyland Blackjack Team

In 1979, Hyland’s blackjack team was four-men strong. Each contributed $4k to the bankroll, giving them $16,000 to work with. By the end of the year, they had built that to $100,000.

Before long, the team had grown to 15, with Tommy Hyland playing the role of manager. He was a strict leader, expecting complete honesty from his team when reporting winnings. No one tracked their hours or their winnings and losses. The team worked entirely as a group effort, and split the winnings equally between them every night.

In December of 1979, with about $50k between them, Hyland’s blackjack team conducted an experiment in bet sizing. For two weeks, they began altering their bet sizes based on the count, wagering higher when a blackjack was more likely, and lower when the count was against them. It was an enormous success, crushing the casino and doubling their bankroll to $100,000.

At that point, Hyland wanted to move the team to Las Vegas, but the other members were keen on the casino action on the other side of the world, as told by Stanford Wong in ‘Blackjack in Asia’. Finding himself working alone once more, Hyland began training his golfing buddies to play blackjack and count cards.

Hyland said he would teach them, test them, and those who were capable (about 19 out of 20), would be assigned to his team. By the end of 1980, Tommy had a whole new crew of 15-20 members. They experienced a few downswings over the years, some more extreme than others, but unlike most blackjack teams throughout history, Hyland’s group has efficaciously withstood the test of time.

Hyland’s success has often been attributed to his superior leadership qualities. He has managed to succeed where many team leaders have failed, by instilling a strong sense of responsibility, loyalty and trust among his team members.

Hyland’s Hardships

Throughout the years, Tommy Hyland has encountered a number of difficulties as a professional blackjack player and card counter. Some came from the casinos directly, and others from the legal side of the fence.

On many occasions, casino managers took it upon themselves to boot card counters from their establishment, especially in the early days of card counting in Vegas. Hyland recalled one such incident in which he was wrangled by security at a Las Vegas casino and forced, at gunpoint, to return the $100,000 he had just won before being tossed out.

In the early 1980’s, just as computers were becoming big business, fellow Blackjack Hall of Famer Edward O. Thorp devised a wearable computer that Hyland was utilizing on a trip to the Bahamas. The casino caught him using the device, and despite the fact that using computers in a casino was not considered illegal at the time, he was arrested. Instead of waiting for a trial, Tommy elected to accept a deal, pay a fine and get back home.

In 1994, Hyland became entangled in what would become a pivotal legal battle for blackjack card counters. While playing at the Casino Windsor in Ontario, Canada, he and his blackjack team were arrested and charged with cheating. As the story goes, several Las Vegas casinos had pushed the court case in an effort to establish a legal precedent against blackjack players who use card counting and ace sequencing skills.

Tommy didn’t back down. He and his team chose to fight the allegations and stand up for the rights of his fellow professionals. Many other blackjack experts came to his aid, including another inaugural inductee to the Blackjack Hall of Fame, Arnold Snyder.

After days of testimony, the judge decided in favor of Hyland’s blackjack team. In the ruling, the judge referenced Snyder’s expert testimony on multiple occasions, declaring that card counters are not cheating. They are simply players with elevated skills who deploy superior intelligence to play the game with a higher rate of success than the average player.

Since his induction to the Blackjack Hall of Fame, Tommy Hyland has devoted much of his efforts towards protecting and cultivating the rights of fellow card counters. As an advocate of fair treatment, Hyland has initiated a number of lawsuits against casino operators who discriminate against card counters.