After retiring, Cross moved into broadcasting. He has co-hosted the YES Network'sThis Week in Football, as well as serving as color commentator alongside John Sterling on the network's Ivy League football telecasts. Cross is also a sideline reporter for the New York Giants Radio Network as well as an analyst on Giants First and 10. He has spent a great deal of time working with youth to help ensure that they stay in school. He currently resides in Northern New Jersey and is a commercial real estate broker in NY/NJ for Cushman & Wakefield; where he works closely with Global Chairman Bruce Mosler. His son, Howard Cross III, recently committed to the University of Notre Dame to play football in the fall of 2019 and his daughter will attend The University of Alabama Honors College.