DiGregorio was born on November 14, 2001, and grew up in Medway, Massachusetts[1][2] When DiGregorio was ten years old, his family attended the White Castle USA Luge Slider Search event, which was being held in the nearby town Carlisle.

[3] He was later invited to the Olympic training facility in Lake Placid, New York, as the luge scouts "liked his build, speed, and strength.

[4] In the 2014–15 luge season, DiGregorio won a gold medal at the Norton Youth B National Championships.

[1] At the end of the 2016–17 season, he won the gold medal at the Norton Youth A National Championship.

[1] "The junior World Cup circuit got shut down, and the senior World Cup circuit got reduced, so Sean Hollander, now my doubles partner, we decided to try and do doubles instead of one of us going to Europe and one of us staying home," he said.