It was the first major mob hit within New York City's five ruling Mafia families in more than three decades.
The syndicate's mostly peaceful hibernation came to an end on Staten Island about 9:30 pm when law enforcement sources say a dozen gunshots were fired likely by a lone assassin, six of them hitting Cali-cutting short his life and his reign over the Gambino crime family.
Cali, 53, had left his house to investigate the sound of crunching metal, according to the NYPD. His car had been hit while parked on the street in front of his home according to New York City chief of detectives Dermot F. Shea. There was a "conversation or an altercation" according to Chief Shea, who indicates that the accident may have been a staged ruse to get Cali out of his house so he could be killed. "It's quite possible that was part of a plan," Shea said.
He was hit by close-range gunfire while his wife and child were still inside their home. Detectives found 12 shell casings at the scene. Cali died a short time later at Staten Island University Hospital North.
Police have reviewed surveillance video from neighboring homes and security recordings from Cali's house. The videos show a minute-long incident on the street, according to Shea, including "muzzle fire" and apparently the actual shooting with a 9mm pistol.
There were initial reports that Cali was also run over by the hitman's blue getaway pickup truck, but authorities now say that didn't happen. Investigators believe that he did try to scramble to safety after being hit by the initial rounds, attempting to take cover behind his Cadillac S-U-V. His bullet-riddled body was found behind the car, leading to the speculation that he had been hit.
Regardless, mobologists consider a hit on a crime syndicate boss at his home to be unusual and possibly a "message murder," even though it isn't apparent what the message to the Gambinos would be.
There has been a recent uptick in Mafia violence the past year in New York, most of it directed at lower echelon hoodlums including the shooting death of Bonanno crime family associate Sylvester Zottola, 71, at a McDonald's drive-thru in the Bronx last fall.
Perhaps that ambush and other less lethal skirmishes were small tremors leading up to the Wednesday night quake.
Authorities on Thursday however said that they were ruling out no motives but Chief Shea said that "Mr. Cali's prior dealings are a focus point." Police are also said to be looking for additional people and vehicles that may have been on the scene at the time of the street ambush.
Investigators say they are considering if Cal's assassination signals the start of a new mob war; whether it could have been a one-off underworld solution to a specific problem or a renegade mob soldier with a beef against the boss.
Typically, crime syndicate slayings of this magnitude are not coincidental and bosses are almost never rubbed out without express approval from upper-level Mafiosi.
The last major mob hit in New York was in 1985 when then-Gambino boss Paul Castellano was shot dead outside Sparks Steakhouse in Midtown Manhattan. Castellano's killing was ordered by the iconic godfather John Gotti-and intended to clear a path for Gotti's immediate ascension to the top of the Gambino family.
Prosecutions and the 2002 prison death of Gotti, known as the "Teflon Don," left Gambino gangland operations in disarray.
Cali was thought to have righted the ship after being posted at the helm of the Gambino crime organization in 2015. Shunning the fancy pinstripe suits and public attention that his predecessors craved, investigators say Cali was a quiet workhorse, refocusing attention on core mob rackets including labor union corruption, loansharking and also on a burgeoning heroin and pain pill trade in New York.
For the NYPD and FBI now looking for motive and suspects in Cali's demise, a complicating factor is his close connection to the Sicilian Mafia. He is a native of Sicily and his wife is the niece of Gambino capo John Gambino. Authorities are considering whether the hit was ordered from overseas and if so, why.
Cali's criminal history is thin. He served only one prison term, 16 months for extortion back in 2008. The conviction, bargained down from a racketeering charge, involved a failed attempt to build a NASCAR race track on Staten Island.
Mob murders are not usually solved. In Chicago, where there have been more than 1400 Outfit-linked killings since before Al Capone's steely rule, only a handful have ever resulted in prosecution.
The past few decades Chicago gangsters have seemingly taken a kinder, gentler approach to their traditionally blood-soaked profession. There have been very few gangland killings here in recent years, although one high-ranking Chicago mob boss is still missing and presumed dead. Anthony "Little Tony" Zizzo hasn't been seen since saying goodbye to his wife and leaving their west suburban home for a meeting in 2006.
New York mob families had practiced a similar peacenik approach-until last night, presuming that Cali was indeed the target of a gangland hit.
Several items are up for discussion by local and federal law enforcement as they gather for their post-crime "roundtable" to discuss the evidence:
Their novel-and successful-defense for the jury was that they had been unfairly profiled because of their Italian heritage and that the Mafia was dead.
A few hours later, at least the latter argument seemed to have been disproved in a hail of bullets.