Born in Chicago, Illinois, Grady attended Lake Forest Academy, a nationally known private school for boys, and graduated in 1948.

He was Chief of the Criminal Division in the Office of the United States Attorney for the Northern District of Illinois from 1956 to 1961.

[2] On October 20, 1975, Grady was nominated by President Gerald Ford to a seat on the United States District Court for the Northern District of Illinois vacated by Judge Edwin Albert Robson.

He served as Chief Judge from 1986 to 1990, and assumed senior status on May 23, 1994.

[3] His service terminated on December 2, 2019, due to his death at his home in Wilmette, Illinois.