Dr. Flanagan was born in Arlington Heights, Illinois and grew up in the suburbs of Chicago. Despite Chicago-area roots, Dr. Flanagan is an avid Green Bay Packers fan, as he spent many summers in the Northwoods of Wisconsin. He received his undergraduate degree from Vanderbilt University, majoring in both Neuroscience and Mathematics. He received his medical degree from The University of Chicago and completed his residency at Case Western Reserve University in Cleveland, Ohio. During residency, Dr. Flanagan received an Allen Fellowship grant which allowed him to perform an additional year of biomechanical and clinical research. Dr. Flanagan received two awards during residency recognizing him as both a distinguished junior resident and chief resident amongst his peers. Dr. Flanagan then completed an Orthopaedic Trauma Fellowship at Florida Orthopaedic Institute.