Oswald Jacoby: The Smartest Card Player of All Time

Oswald Jacoby: The Smartest Card Player of All Time

Tuesday, 1 February 2011

By Johnny Hughes.

Oswald Jacoby (1902-1984) was one of America's best all-round card players. He wrote books on poker, gin rummy, contract bridge, backgammon, canasta, gambling and probability. He started winning at poker at the age of eight, playing with older boys. At 15, he lied about his age to join the army in the First World War for the last two months of the war. He spent all his time playing poker and saved $2,000 in winnings.

Jacoby dropped out of Columbia University at 21 when he became the youngest licensed actuary in New York history, calculating probabilities for insurance companies. As he pointed out, insurance was gambling and it started out illegal. Jacoby could make seemingly impossible calculations in his head, such as multiplying five numbers by five numbers (as in 32,493 x 97,735). He could also look through a deck of cards and quickly memorise the location of all 52 cards.

By 23, Jacoby was a regular gambler at New York's legendary Cavendish Club, where the best card players in the country gambled with millionaires. Another regular gambler at the Cavendish was Harold Vanderbilt, from America's richest family. As a yachtsman, Vanderbilt won the World Cup three times. The Cavendish was located at the Mayfair Hotel, where Vanderbilt had a suite of 15 rooms. Vanderbilt invented contract bridge in 1925 which, along with poker, became one of America's favourite card games.

Jacoby, affectionately called Ozzie, quit work at 28 to spend his life playing games, gambling on games and writing about games. He first gained international fame in a celebrated bridge match with partner Sidney Lenz against the most famous couple in bridge, Ely and Josephine Culbertson, a match that was written up in newspapers across the country. Jacoby's legendary temper led him to quit after many days.

It was contract bridge that made Jacoby famous. From the 1930s to the late 1960s, bridge tournaments were huge in America. They were held in the fanciest hotel ballrooms and the eccentric, brainy, quirky, conceited stars like Jacoby were written up often in major magazines such as Time, Life, and Sports Illustrated.

At the Cavendish and other New York gambling spots, Jacoby played his four big games: poker, gin rummy, bridge and backgammon for high stakes, and he won. He formed a bridge team from the young gamblers at the Cavendish, the Four Aces, that dominated bridge tournaments in the 1930s and won the world championship from the French at Madison Square Garden. Meanwhile, Jacoby wrote over 10,000 articles on bridge for his syndicated column, carried in newspapers all over the country.

In 1937 Jacoby moved to Dallas, Texas, a big gambling town. He played in the largest poker games with oil millionaires and expert players even though they were above his bankroll. He won. In 1940, he wrote his first book on poker. Directed at home games, it covered the rules, ethics, etiquette, stakes, strategy, probability, deception and tells. He wrote about high and low draw, five- and seven-card stud, and high-low split, but not Texas Hold’em.

When one of America's richest men, Dallasite H.L. Hunt, lost $250,000 to gambler Ray Ryan playing gin rummy, Hunt hired Jacoby to teach him expert play. This friendship helped Jacoby enter some of the largest and most secret Texas poker games.

When America entered the Second World War, Jacoby got a substitute to finish a national bridge tournament and joined naval intelligence where he became a lieutenant commander. His group broke the Japanese and German codes. When the Korean War started, Jacoby went back to the Navy for the duration. They called to say, "We need a computer”. They meant his amazing trick brain. He was a true patriot and served in three wars.

When I was 20, I began to travel the bridge tournament circuit and became a Life Master, the highest rank. Like poker now, one of the attractions of bridge was that the common man could complete with the best and most famous players in the world. I played against and watched Jacoby often. He was always the most famous person in the room, with tufts of grey hair, a childish grin of warm enthusiasm and restless energy.

Playing against him was intimidating because there was a small group of kibitzers and he was the fastest player in the world. Jacoby would open his hand and glance at his 13 cards without sorting them into suits like everyone else. Then he would bid or play at breakneck speed, never looking back but always pulling the correct card from his hand. He always seemed to be rushing his opponents. He estimated that he spent six years of his life waiting for other people to play in card games. People described Jacoby alternatively as a genius, childlike and the most impatient man of all time.

When Jacoby was the dummy or the round was over, he would bound from the table to walk all around the room, talking with everyone, doing a crossword puzzle rapidly, making prop bets, checking sports scores and appearing to have great fun. He was very friendly and approachable and would answer all of my questions. People would come up to Jacoby and ask him to remember a tournament hand from 40 years back and he'd recall all the cards and the outcome. I've never known of anyone who could match his mental tricks.

I once saw Jacoby go behind the scoring table right after a bridge tournament while the scores were being added up. He glanced over the sheet and announced, correctly, the first-, second- and third-place winners, adding all those numbers in his head.

My mother and I appeared on Jacoby's TV show which was a bidding contest against another pair. We would bid the hands which were shown on the screen and Jacoby would give a critique. Then my feisty mother would tell him in an angry voice that he was wrong. Jacoby was known for his mercurial temper but it did not come into play and I never witnessed it personally.

Once in Dallas there was a Calcutta pool with cash prizes. The entering pairs are auctioned off with the bids making up the prize pool. I was travelling with bridge great Butch Adams and Jacoby bought us for the minimum bid of $40. I was embarrassed no one else bid. By custom, you have half your action. The prize pool became large due to ego bids, friendship bids and Dallas money. We played poorly. The next morning we drove to Oklahoma City for a large Open Pairs. The tournament had hundreds of people. We only knew three pairs to bet the last of our road bankroll with. We placed fifth and lost all three bets to first, third, and fourth.

That same year, Johnny Moss took me as a partner and stake horse in an auction bridge game in Odessa, Texas. We lost. Gamblers played gin rummy and auction bridge before the poker game started, but poker was king.

I watched Jacoby shoot dice. He was betting the front side, hard-ways and having a blast. I also watched him play gin rummy. His first discard was his lowest card. If you discarded first, he would discard a card that touched yours. If you threw an eight, he'd throw a seven or nine. As in other games, he played rapidly, never seeming to think. His book on gin rummy is still the classic.

In the fifties there was a gin rummy cheating scandal at the Frair's Club in Los Angeles. Many show business celebrities lost millions. A man in the ceiling with a peep hole would send radio signals to a device worn on the cheater's waist. One of their victims was Oswald Jacoby who testified at the trial, "They seemed like good players. No wonder I couldn't beat them." It seems to me the giant brain would have caught them.

When he was in college, Jacoby won a chess match against the world champion. Forty years later, he played the Russian world champion to a draw at lightening chess; however, chess was just too slow for him.

It was for bridge that he was most famous, authoring six major bridge books. I still play his most famous bidding conventions: the Jacoby Two No Trump, the Jacoby Transfer, weak jump overcalls, and limit raises.

All bridge tournaments award Master Points. While away at two wars, Jacoby fell far behind his fellow experts in the race for the most Master Points of all time. Each year, the McKenney trophy is given to the player who wins the most Master Points that year. Even though no one over 50 had ever won it, Jacoby won the most Master Points the years he was 57, 59, 60, and 61. The McKenney race requires constant travel to bridge tournaments and is a test of stamina. He swam each day a pool was available to stay in shape and he often selected very young partners. This made him the all-time Master Point leader for awhile. He had won more national and international championships than anyone except his old Cavendish days buddies and team mates John Crawford and Howard Shenken.

Oswald Jacoby retired from the Master Point race but he never stopped gambling. He won national backgammon titles three years in a row, in 1966, 1967 and 1968. He then wrote the first scientific book on backgammon in 1970. The Jacoby Rule is named for him. A player can challenge to double the bet. His opponent must accept or concede the match. Of course, it speeds up the game and increases the action. Jacoby won the World Backgammon Championship in 1972, when he was 69.

Expert backgammon players have included poker greats Stu Ungar, Paul Magriel, Dan Harrington, Erik Seidel and Gus Hansen. Ozzie said a fast backgammon player can beat a good backgammon player 40% of the time.

When Jacoby was 74, Sports Illustrated profiled him as an all-around gambler. He was still playing high stakes gin rummy and poker at the Dallas Country Club. Never known to be modest, Jacoby said, "I am the best 74-year-old player of any game. Bridge, backgammon, poker, gin rummy – any of them. I play bridge better today than I did 40 years ago."

When asked who won or lost at gambling or the stakes they played, Oswald Jacoby, with the greatest memory of all time, would always say he did not remember, and flash his childlike grin.

Johnny Hughes is the author of Texas Poker Wisdom, which is available from Amazon.

Tags: johnny hughes, columnist