Police said surveillance video captures the shooter, and the pick-up believed to be the getaway truck.
EMS responded to the scene and transported Cali to Staten Island University North where he was pronounced dead.
Someone called 911 about the crash - in addition to other calls about shots fired out on the street, sources said.
Shea says Cali emerged from his home around 9:15 p.m. after the suspect backed his pickup truck into Cali's Cadillac SUV.
Cali's murder is the first hit on a Mafia boss since John Gotti arranged the assassination of then-Gambino head Paul Castellano in 1985.
A reputed NY crime boss was shot and killed outside a home Wednesday night.
Later that year, he pleaded guilty to extortion conspiracy related to the planned construction of a NASCAR speedway on Staten Island - a plan that eventually was scrapped.
He died in prison in 2002, leaving a notorious legacy that cemented New York's place in mob lore.
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NY media say it is the first targeted killing of a mob boss in the city since 1985.
He was reputed to be the boss of the Gambino crime family.
The Gambinos" rise to become one of the most powerful mafia families in America started in 1957, when the family's namesake, Carlos Gambino - an Italian immigrant - orchestrated the murder of Albert Anastasia, who had organized a collection of Italian gangs into what now would be considered a "crime family'.
It had been decades since a Mafia boss was hit in NY. "But I guess old habits die hard".
"Frank Cali was a pretty likeable guy, and also this is not a way the mob would kill one of their own", he said. He served a 16-month sentence.
"Cali is seen as a man of influence and power by organised crime members in Italy", US assistant attorney Joey Lipton told the court, the New York Daily News reported at the time.
Last October, 71-year-old Sylvester Zottola, a reputed associate of the Bonanno organisation, was shot dead at a takeaway restaurant in the Bronx, New York.
In that case, authorities intercepted conversations shedding light on his quiet underworld command.