Gregory Scarpa Sr. (May 8, 1928 – June 4, 1994) nicknamed the Grim Reaper and also the Mad Hatter, was an American caporegime and hitman for the Colombo crime family, as well as an informant for the FBI. During the 1970s and 80s, Scarpa was the chief enforcer and a veteran hitman for Colombo boss Carmine Persico. He is suspected by the FBI to have murdered at least 100 people over the course of his criminal career. He was sentenced to life in prison in 1993 for three murders, and died on June 4, 1994.
Scarpa was born to first-generation immigrants, Salvatore and Mary, from the small village of Lorenzaga of Motta di Livenza near Treviso, Italy. He was raised in the working-class neighborhood of Bensonhurst in Brooklyn. As a child living in the Great Depression, Scarpa helped his father deliver coal throughout New York City. His older brother, Salvatore Scarpa, may have introduced Gregory to the Colombo crime family which he reportedly joined in the 1950s.
In the 1950s, Scarpa married Connie Forrest; she and Scarpa had one daughter and three sons, including Gregory Scarpa Jr., who would follow his father into the Colombo family, eventually becoming a capo. Scarpa and Forrest separated in 1973. Scarpa also maintained a 30-year relationship with girlfriend Linda Schiro that resulted in two children, Joseph and Linda.
Scarpa was a stylish dresser who routinely carried $5,000 in pocket money for purchases and bribes. He had use of an apartment on Manhattan’s Sutton Place and owned homes in Brooklyn and Staten Island, as well as Las Vegas, Nevada, and Singer Island, Florida. His power, guile and brutality earned him the nickname “the Grim Reaper” and helped him escape prosecution for many years. Schiro later said that Scarpa would sometimes leave the numbers “666”, the biblical Number of the Beast, on his victims’ pagers.
A career criminal, Scarpa eventually became a caporegime in the Colombo family, as well as the proprietor of the Wimpy Boys Social Club. Scarpa was involved in illegal gambling, loansharking, extortion, hijacking, counterfeit credit cards, assault, stock and bond thefts, narcotics and murder. Many of the highest-ranking members of the Colombo family today were members of Scarpa’s crew. In March 1962, Scarpa was arrested for armed robbery. To avoid prosecution, Scarpa agreed to work as an undercover informant for the FBI, beginning a 30-year relationship with the agency.