Education
He attended Saint Margaret Mary Parochial Elementary school grades 6-8 then attended Monsignor Farrell High School before transferring to Curtis High School.
He attended Saint Margaret Mary Parochial Elementary school grades 6-8 then attended Monsignor Farrell High School before transferring to Curtis High School.
He was signed by the San Diego Chargers as an undrafted free agent in 2006. He played college football at Syracuse. Gregory lived in Staten Island, New York for most of his youth.
He was a Jets fan growing up.
He played college football at Syracuse University. San Diego Chargers
Gregory signed with the San Diego Chargers as an undrafted free agent in 2006.
He played for them until 2011. He started 31 of 85 games, recording 241 tackles, four interceptions and two sacks.
New England Patriots
On March 15, 2012, Gregory signed with the New England Patriots.
On Thanksgiving Night—November 22, 2012—Gregory had a primary role in the Patriots" victory over his home-town team, the New York Jets. In the game, Gregory had an interception, 2 recovered fumbles (one leading to a touchdown, during the now infamous Butt-Fumble play), 5 tackles, and 1 pass deflection. Gregory was released by the Patriots on February 28, 2014.
Kansas City Chiefs
Gregory was signed by the Kansas City Chiefs on July 31, 2014.
Retirement
Gregory announced his retirement from football on August 9, 2014. On June 4, 2015, the Syracuse athletic department announced Gregory would return to his alma mater as a Special Teams Quality Control coach.
Gregory was also a member of the New England Patriots and Kansas City Chiefs.