Witnesses said Cali's killer shot him at least six times and then ran him over before fleeing the scene.
No arrests have been made at this time. His head was by his SUV, and the truck was open'.
A panicked family member called 911, telling a dispatcher Cali was deliberately run over before he was shot, sources said.
Cali was taken to a hospital where he was pronounced dead.
One woman yelled into her phone, "Why doesn't the ambulance come?"
Cali was believed to have been elevated to the position of acting boss in 2015, taking over from Domenico "Greaseball" Cefalu.
The last crime family boss to be shot in New York City was Paul Castellano.
The organization reportedly focused its efforts on heroin and Oxycontin trafficking under his leadership.
Cali was "a real quiet old-school boss", a police source told The New York Post.
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They were the only suspects in custody after four North Korean suspects fled the country on the morning Kim was killed. While Indonesia lobbied for Aisyah's release, Vietnam has been more reluctant to get involved in a red family feud.
His only mob-related criminal conviction came a decade ago, when Cali pleaded guilty in an extortion conspiracy involving a failed attempt to build a NASCAR track on Staten Island.
The Gambino crime family is one of what is widely referred to as "The Five Families" of Italian organized crime operations in New York City and other parts of the United States.
In 2008, Cali was arrested and charged with federal racketeering as part of Operation Old Bridge - a code name for the February 7 arrests in Italy and the US that targeted the Gambino crime family.
Gambino headed the organization until 1976, when he handed power over to his brother-in-law Paul Castellano.
The influence of the Gambinos waned in the 1990s after a number of members turned government informers and several leaders were imprisoned.
In 2012, Cali was identified as the new underboss of the Gambino crime family. It has been led in the past by infamous mobsters such as Carlo Gambino and John Gotti.
Cali was first reported to be in charge of the Gambino family in 2015.