Russillo spent most of his childhood in Connecticut, before his family moved to West Tisbury, Massachusetts when he was a teenager.

He is a 1997 graduate of the University of Vermont, where he was a member of Sigma Alpha Epsilon and was also an intern at WCAX in Burlington.

Before moving to West Hartford, Connecticut in the late 2000s, Russillo lived in Boston, Massachusetts, where he hosted The Die Hards (mid-2003 to 2005) with co-hosts Anthony Pepe, Jon Anik, Kevin Winter, and Mike Winn while working for the Sporting News Radio affiliate WWZN.

He was let go after, and possibly as a result of, a personal conflict with John Dennis of WEEI, who had left him a threatening voicemail.

"[5] He appeared regularly on several shows on Comcast Sportsnet New England, including New England Sports Tonight with Gary Tanguay and Greg Dickerson, and was also a studio analyst for the Boston Celtics' television coverage.

Kanell was laid off from ESPN in April 2017, leaving Russillo as the sole host again, with multiple guest co-hosts occasionally joining him on the show.

[15] On August 23, 2017, Russillo was arrested in Wyoming for criminal entry, reportedly while nude and intoxicated.