Judge Harry Milton Montgomery, Sr., was born in Pittsburgh on June 12, 1901. He attended Allegheny High School, the University of Pittsburgh, and the University of Pittsburgh Law School.
After graduation, Judge Montgomery began his twenty years in private practice. He established the firm of Ralph and Montgomery. Apart from his law firm, Judge Montgomery spent a year working as an assistant county solicitor. Additionally, Judge Montgomery was a member of Pittsburgh’s professional hockey team, the Pittsburgh Yellow Jackets.
In 1943, Judge Montgomery was elected to the County Court of Allegheny County. Judge Montgomery remained in this position until his election to the Superior Court in 1959. In 1971, he reached the mandatory retirement age and became a senior judge on the court.
Judge Montgomery continued to serve the Superior Court as a senior judge until his retirement in 1995. At this time, he was the oldest appellate judge in the history of the Commonwealth, leaving behind a 71-year career in law. Judge Montgomery passed away on August 29, 1999.