Gregory has been following the NFL since his youth. For the last 7 years he has used the internet to offer fans his NFL weekly predictions and over the past few years he got involved with mock drafts. He has played fantasy football for 15 years managing various leagues and offering innovating scoring systems such as the points per yard when other leagues used to score only 100/300 yard games. His has been on the radio to talk about the NFL Draft, as well as being future on websites such as CNNSI.com.  He also was a finalist for the FoxSports.com's first Next Great Sportswriter competition. As a resident of the Bay Area his loyalties lie with the Oakland Raiders. He is also a season ticket holder for the California Golden Bears.