Theodore James Sierad was born on August 13, 1952 in New York to Theodore B. and Joanne Sierad as the second eldest of five children. He grew up in Harrison, New York and graduated from Salesian High School in New Rochelle, New York..​

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Growing up, Ted spent summers on the water​. He cherished visiting his maternal grandmother who lived in Mystic, Connecticut, family outings on his parents' boat, to visiting his paternal grandparents who lived on the water in Florida. All this contributed to his life-long love of the water. Summers also included family camping. In the winter, he enjoyed ice boating and skiing with his family. Ted would spend hours working on fixing up his cars with special memories of his father's help.

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It was when he was home on a break from college in 1972, he leafed through a book of careers on his parents' coffee table and read about the opportunity of being an airline pilot.