In the game of pool there is an art to winning. Some men have a natural talent for playing the game and any version of it. Tugboat Whaley, real name unknown, was one that had talent. You might consider him a gambler given that he bet on games like pool in order to win money. Of course, the most common word for what he did would be pool hustler. He was definitely a hustler with a powerful reputation as being great.
According to one account of this man he used to wear rain gear. He would have the rubber hat and everything else for rain gear. Most thought he looked like a captain of a tugboat, thus the name Tugboat Whaley. Chances are Whaley was his last name, but you might not know it as truth given that it is highly difficult to find any mention of this man outside of the legends. Many believed that he actually was a tugboat captain before he retired. It was thought he had a pension, but was very idle so he took up the game of pool and began hustling.
Of course, this is all just speculation of the true man. What is more likely to be true is that Whaley like Mosconi had an affinity for pool. He decided that playing professionally would be the smartest way to go in order to live in luxury. He probably even had the need to hustle because the rest of life would be boring. Given his penchant for not telling anything about himself including his real name, he was probably one of the world’s greatest actors affecting a character that earned a reputation as a pool player. For most who would see Whaley dressed up in his rain gear and tugboat captain appearance they would think he wouldn’t know much about the game or even be able to win. It would mean high bets against him and great amounts of money earned.
His line was certainly telling those he played that he was a retired captain, so perhaps it is true. After all the greatest hustlers and lies always stick to the truth in some part in order to make it sound all the more real. He was always asking for just a friendly game according to the accounts about him. In some reports he would play 100 balls during the break, take the money and be a rich man.
What made Tugboat Whaley so great was that he would move around. He would always find new marks with men who had never heard of him. It made it easy to make certain he could break the pool balls, get them all in, in one shot and ensure that he went away with a few hundred each time. The thing with pool back in the early 1900s was that the money gambled was small in comparison to today, yet because money could buy many things on the cheap he was considered fairly well off by the standards he lived in.