Tom was born in Boston in 1952 and grew up in Southborough, Mass., where his father taught at St. Mark's School. He went to Fay, a local elementary school, and then for a year to Winchester College in England where his father taught on an exchange program. Fay, founded in 1866, imbued in its students a strong and enduring sense of discipline and tradition, qualities taken to even greater heights at Winchester, which was founded in the late 14th century, and which takes as its motto, "Manners Makyth Man".

After a year at Winchester, he went to Milton Academy, graduating in 1970. Leadership seemed to come naturally to him; he was Head Monitor at Milton and captain of the football team there as he had been at Fay.

He went on to Harvard ('74) and then to Hofstra Law School where he graduated with distinction in 1979 and was Editor-in-Chief of the law review.