Earning a degree in Government from Franklin and Marshall College (F&M) in Lancaster, Pennsylvania, Dee also played collegiate basketball and is a member of Sigma Pi fraternity.
Dee joined the San Diego Padres in 1995 as the director of corporate development, and was promoted to senior vice president of business affairs, working under one of his mentors, Larry Lucchino in 1999, remaining with them until 2002.
In 2004, Dee turned down an offer to become president of the Los Angeles Dodgers[3] to take on an expanded role with the Red Sox, which included becoming president of Fenway Sports Group (FSG), a sports marketing and investment entity conceived with John W. Henry to diversify and expand Red Sox' business interests beyond Major League Baseball.
Just prior to his departure in 2009, he consummated a $78 Million, thirty-year agreement with Lee County, Florida for a publicly funded spring training complex, known today as JetBlue Park.
[6] In addition, Dee consummated a record 10-year radio partnership with Entercom Communications, establishing a key relationship with CEO, David Field, in 2005.
[7] Dee's successful tenure with the Red Sox and Fenway Sports Group concluded in May 2009, when he was offered the role of CEO of the Miami Dolphins.
This transformation was the foundation for the present day Padres of the 2020s where veterans Eric Hosmer and Manny Machado have been added to this young core (post Dee's tenure) to position the franchise for a successful decade.
[17][18] Dee joined Audacy after CEO David Field recruited him upon the merger with CBS radio in 2017 to create the largest audio sports platform in the country.
In October 2020, Dee lead the Audacy team in consummating what was reported[21] as the largest single advertising partnership in the history of the radio/audio industry with FanDuel and their agency, Ad Results Media.
Dee also played a lead role in Audacy's acquisition[22] of the QL Gaming Group – a digital sports betting data analytics platform – and their app BetQL.