From 1993 to 1997, DeGregorio was head boys' basketball coach and athletic director at St. Thomas Aquinas High School of New Britain, Connecticut.

[3] It was widely believed that DeGregorio recruited Odom not to play basketball, but to ensure that he could receive a high school diploma.

He moved to Rhode Island in 1997 as top assistant to Jim Harrick, shortly after Lamar Odom transferred from UNLV.

In rapid succession, four prospective recruits dropped URI from their lists, another was ruled ineligible, and a key reserve was lost to academics.

[5] DeGregorio served in that position until 2003, when he began working as an independent skill development coach for many star NBA players.