McMonagle became an Associate with Kelley & Ferraro in 2004. Previously, he had been a Law Clerk at the firm. He was graduated from St. Ignatius High School in 1994 and from the University of Vermont in 1998 with a BA in Philosophy. He attended the Cleveland-Marshall College of Law and was graduated in 2004. McMonagle is admitted to practice law in the State of Ohio and the United States District Court for the Northern District of Ohio. McMonagle is an experienced trial lawyer and was recognized in Super Lawyers Magazine as a Rising Star in 2011, 2012, and 2013. He also served as a Magistrate for the Rocky River Municipal Court.