He previously covered intelligence and counterterrorism for Foreign Policy and spent over 20 years at Army Times, with stints as an embedded reporter with troops in Somalia, Haiti, the Balkans, Afghanistan and Iraq.
Born in 1966 in Calgary, Alberta, Canada to British parents, a geologist and a journalist, Naylor earned a master's degree in international relations in 1990 from Boston University.
In January 2002, the 101st Airborne Division (Air Assault) took a couple dozen journalists, including Naylor, into Afghanistan with Task Force Rakkasan.
Naylor spent almost four months covering the War in Afghanistan, including several days in the Shah-i-Kot Valley at the start of Operation Anaconda.
With this information, Naylor wrote his second book, Not a Good Day to Die: The Untold Story of Operation Anaconda, published in 2005.