King of the Hill

Celebrating the life of Joe DeGregorio, former federal agent and ambassador of St. Louis’ famed Italian-American neighborhood.

Joe DeGregorio
Photo by Carmen Troesser

Published on Show Me Mizzou Dec. 19, 2024
Story by Amanda E. Doyle, BJ ’94 

Within five minutes of meeting Joe DeGregorio, BJ ’70, you’d know about at least three of his life’s passions: his family (Catholic, Italian and large), his alma mater (Mizzou) and his neighborhood (St. Louis’ famed Italian-American enclave, the Hill). Chances were, he’d be wearing a sweatshirt representing one of the above.

The eldest of seven children and the first grandchild in a family that grew to have 24, DeGregorio’s path eventually led him great distances away from St. Louis. He graduated from high school and headed to Mizzou, where he earned a bachelor’s degree in broadcast journalism and was a proud member of Delta Sigma Phi. After serving in the military as a chaplain’s assistant during the Vietnam War, he pursued a decades-long career as a federal agent, working for the then-Defense Security Service in stations from Kansas City to Long Beach, CA, where he added a master of public administration degree to his accomplishments.

No matter where he lived, DeGregorio — his family and friends knew him as Joey — considered the tight-knit Hill community of neighbors, businesses and St. Ambrose Catholic Church as his home. After his 2005 retirement, he returned and found a new purpose in leading popular tours of the district. His father, Roland, had offered those same tours for 25 years. 

On any given day, you’d find Joe strolling among the numerous restaurants (he had eaten at every one), bakeries, coffee shops, stores, bocce courts and other institutions that draw locals and tourists alike. He was always leading a tour or trying to hustle one up. His license plate, “DEHILL,” gave him away on the rare occasions he strayed from the neighborhood. His demeanor was mischievous and irrepressibly fun, and his dance moves — often on display to tour groups — were legendary.

As part of his mission to honor his heritage, DeGregorio contributed to projects documenting the history of the Hill. He was interviewed on-screen for the film America’s Last Little Italy: The Hill, contributed the introduction to a history book on the area and, in 2022, wrote a full-color walking tour guidebook of his own, The Hill: A Walk Through History. Promoting the book with a media blitz through St. Louis brought his broadcast journalism education back to the fore: “This is a totally different gig and I’m enjoying every minute of it,” he said. A series of short promo videos on YouTube capture “Joey on the Hill!” hamming it up in some of his beloved haunts.

Josh Stevens, whose Reedy Press published DeGregorio’s guidebook, remembers that DeGregorio, grappling with a recent cancer diagnosis, at first “couldn’t guarantee that he would finish the work. But he had too much pride and loved the Hill too much to let the project falter,” Stevens said. “Not only did he complete his work on time, he shared the joy of his accomplishment with everyone he knew.” 

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