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Kassal was born in Harlem, New York on 28 February 1917. His parents were Polish immigrants. At a young age, his family moved to the Bronx. His family did well economically when he was young. He attended public schools in the Bronx. He attended a high school for boys only. Kassal graduated high school at the age of 16. He was athletically gifted. He attended New York University for one year, but did not like traveling back and forth by subway. A friend told him about the University of Alabama and their football program. He attended college there for one year.Kassal decided to attend an academically driven school to better his chances of attending law school. He applied to the University of Pennsylvania and was accepted. He graduated after three years of college and played for the school's football team before fracturing his left arm and right hand. He attended Harvard Law School and played rugby for the school's team. He had never played rugby before, but he excelled in the sport. He graduated from Harvard Law School towards the top of his class in 1940. He was well informed about the war in Europe and he felt they could join the war shortly.Kassal found a job as a lawyer with an alcohol distributor for $10 per week, he found a better paying job six months later and worked there until World War II broke out. He remembers being at the New York City polo grounds when he found out about the attack on Pearl Harbor.

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