As VP and Editor in Chief of Premium Publishing at Dotdash Meredith, Kennedy oversees special editions across a wide range of subject areas under numerous in-house and partner brands.

A contributor and commentator on talk radio as well as on television, Kennedy has appeared on Late Night with Seth Meyers, Morning Joe, MLB Network, NPR and other news entertainment programs.

He occasionally hosts public speaking engagements focusing on issues and ethics in sports and historical and current events.

Kennedy's new book, The Ride: Paul Revere and the Night that Saved America will be published by St. Martin's Press on March 25, 2025.

He is the author of True: The Four Seasons of Jackie Robinson (2022, St. Martin's Press), as well as The New York Times Bestsellers Pete Rose: An American Dilemma (2014), described this way by the novelist Richard Ford: "Like the best writing about sport–Liebling, Angell–it qualifies as stirring literature" and 56: Joe DiMaggio and the Last Magic Number in Sports (2011), which was called "the best baseball book to appear in many a season," by Roger Kahn.