During his football career, Woodruff obtained his Juris Doctor from Duquesne University School of Law, subsequently becoming a founding member of the law firm Woodruff, Flaherty & Fardo, LLC out of Shadyside in Pittsburgh. Woodruff was elected in 2005 to be a Judge in the Court of Common Pleas in Allegheny County, Pennsylvania.
Judge Woodruff is married to Joy Maxberry Woodruff. They are the parents of three children; Jillian an Ob/Gyn Physician, Jenyce an attorney and John a law student at the Duquesne University School of Law.
Woodruff is a 1979 graduate of the University of Louisville in Kentucky, where his football jersey hangs in Papa John's Cardinal Stadium and where athletes study at the WOODRUFF ACADEMIC CENTER named in Woodruff's honor in 2007 upon a significant monetary donation.
Judge Woodruff and his wife Joy are currently chairpersons of the "Do the Write Thing" in Pittsburgh. The program is an Initiative of the National Campaign to Stop Violence (NCSV). The Do the Write Thing Challenge gives middle school students an opportunity to examine the impact of youth violence on their lives in classroom discussions and in written form by communicating what they think should be done to change our culture of violence. By encouraging students to make personal commitments to do something about the problem, the program ultimately seeks to empower them to break the cycles of violence in their homes, schools and neighborhoods.