Simmons gained fame as "The Boston Sports Guy" which earned him a job offer from ESPN in 2001 to write three guest columns. His second column was "Is Clemens the Antichrist?" which became one of the most e-mailed articles on the site that year. Becoming one of the most popular columnists on the site, Simmons was given his own section of ESPN.com's Page 2, which helped both himself and Page 2 gain widespread popularity. In the first sixteen months which Simmons wrote for Page 2 the viewership doubled. In late 2004 ESPN launched an online cartoon based on his columns which Simmons later called a "debacle" and decided to stop. Simmons wrote a column per month for his page titled "Sports Guy's World."