- 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.
- 2011, Emmy — Outstanding Nonfiction Series: Nominee
- 2014, Emmy — Outstanding Short-Format Nonfiction Program: Winner
- 2015, Producers Guild Awards — Outstanding Producer of Non-Fiction Television: Nominee
- 2016, Producers Guild Awards — Outstanding Producer of Non-Fiction Television: Nominee
- 2017, Producers Guild Awards — Outstanding Producer of Non-Fiction Television: Nominee
- Kari Crichton — Wife
- Ben Simmons — Son
- William Simmons — Father
- Zoe Simmons — Daughter
- College of the Holy Cross, Greenwich, Massachusetts, United States (BS in Political Science, 1992); Boston University, Boston, Massachusetts, United States (MA in Print Journalism)
- Birth Name: William J. Simmons
- Birth Place: Worcester, Massachusetts, United States
- Profession: Author, Journalist
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