Chief Justice Drew was born in Pittsburgh on April 27, 1877. He was educated in public schools, then attended Columbia University where he received A.M. and LL.B. degrees. During his career, Chief Justice Drew was awarded honorary LL.D. degrees from Duquesne University, the University of Pittsburgh, St. Francis College, and Dickinson College.
Following his educational years, Chief Justice Drew was admitted to the bar associations of Allegheny County and New York. From 1906 to 1912, he served as assistant city solicitor of Pittsburgh. In the fall of 1919, he was elected judge of the Court of Common Pleas of Allegheny County. Chief Justice Drew remained in this position until his appointment to the Superior Court eleven years later. He served on the Superior Court for less than a year before his appointment to the Supreme Court of Pennsylvania.
Chief Justice Drew spent 21 years on the Supreme Court, eventually attaining the position of Chief Justice. He retired a year before his death in 1953.
During World War I, Chief Justice Drew served as a captain in the United States Army.