Born in Hartford, Connecticut, Squatrito received a Bachelor of Arts degree from Wesleyan University in 1961 and a Bachelor of Laws from Yale Law School in 1965.
He was in private practice of law in Manchester, Connecticut from 1966 to 1994, and was a counsel to the Town of Manchester Housing Authority from 1972 to 1979, and to the Connecticut State Legislature Judiciary Committee from 1974 to 1975.
On July 28, 1994, Squatrito was nominated by President Bill Clinton to a new seat on the United States District Court for the District of Connecticut created by 104 Stat.
He was confirmed by the United States Senate on October 6, 1994, and received his commission the following day.
He assumed senior status on November 1, 2004 due to a certified disability.