First writing experience came from a steady column called "Ramblings" in The Crusader, Holy Cross's school paper; later served as the paper's sports editor.
Worked for the Boston Herald soon after college covering high-school sports and penning sports profiles and editorials; also freelanced for the Boston Phoenix.
Gained notoriety with a column dubbed "Boston Sports Guy" for an online site called Digital City Boston; it earned him an offer from ESPN.
Left the Boston area after being hired to work as a writer on Jimmy Kimmel Live; he left the show to write full-time for ESPN.
Columns appear in ESPN.com's "Page 2" section; formerly wrote a column for ESPN The Magazine, calling it quits in July of 2009 after seven years.
Executive producer for ESPN's documentary series, 30 for 30.
Hosts a podcast on ESPN called the BS Report; interviews tend to be sports-focused but guests range from sports analysts to actors to comedians, and even to friends.
Authored the books Now I Can Die in Peace: How ESPN's Sports Guy Found Salvation, with a Little Help From Nomar, Pedro, Shawshank and the 2004 Red Sox and The Book of Basketball: The NBA According to The Sports Guy.
Created a recurring cartoon short that appeared on ESPN.com called the The Sports Guy.