DeGregorio has been involved with the sport of hockey as a player, coach, owner, and administrator since 1971. From 2003 thru June 2015 he has been President of USA Hockey and its Foundation. He now serves as co-chairman of those organizations.
DeGregorio is the Chairman of the PenFacs Group he wounded in 1977 and specializes in investment and insurance.
He is also the founder of HARP Insurance Company, which is owned by USA Hockey and specializes in insurable risks in hockey, and served as its President from its founding in 2002 to 2010.
Previously he also served on the Board of PANOL, an insurance captive owned by the United States Olympic Committee (USOC) from its inception in the mid-1980s through the mid-1990s and led a group of investors in 1995 and was the managing partner of the Kentucky Thoroughblades of the American Hockey League. The team was the San Joe Sharks primary development team. He ran the day to day operations of the team through the year 2000.
DeGregorio was selected in 2003 a recipient of the prestigious “Lester Patrick Award” presented by the NHL for service to hockey in the USA. He was inducted in the United States Hockey Hall of Fame in December 2015.
DeGregorio currently serves on the Board of Directors of The Hockey Hall of Fame in Toronto, Canada.