Perhaps most notable for his political blogging work for Esquire and for his sports blog for ESPN, he is also recognized for his Boston Herald Sports column and for his pieces for Sports Illustrated, the Chicago Tribune, the New York Times, and many other prominent publications.
Upon earning a journalism degree from Marquette University, he worked as a Massachusetts forest ranger before beginning his journalistic career with Worcester Magazine.
He often contributed to the National Public Radio (NPR) shows Wait Wait...Don't Tell Me! and Only A Game.
A graduate of St. John's High School, he spent his youth in Shrewsbury, Massachusetts.
He made numerous contributions to Stephanie Miller's popular radio show.