A look into 'Franky Boy' Cali — the alleged mob boss assassinated in New York

The purported head of the notorious Gambino crime family was killed.

The suspected assassination of an alleged mob boss is raising questions about why he was targeted and the internal struggles in what — once — was one of the most powerful American mafia families.

Francesco "Franky Boy" Cali was gunned down outside of his Staten Island home Wednesday evening in what experts view as "a true hit."

"We’re back to the '90s," said Rich Frankel, a former FBI special agent in charge of the criminal division in New York and current ABC News contributor. "We haven’t had a hit like this in at least 30 years."

Robert Boyce, the former New York Police Department chief of detectives who is now an ABC News contributor, said that Cali was a protégé of John "Jackie the Nose" D'Amico — a former prominent figure in the Gambino family.

"He’s an interesting man because he came up in the organization without many arrests," Boyce said of Cali.

Cali was arrested and convicted at least once, which pales in comparison to other mob leaders. In 2008, Cali was sentenced to 16 months in prison after pleading guilty to extortion conspiracy, according to federal court records.

"This guy was really good. He kept a low profile," Boyce said.

Beyond his own deep ties to the Gambino family, Cali had another important connection: his wife, Rosaria Inzerillo, of the Sicilian Inzerillo Mafia clan.

Boyce said Cali’s wife "is steeped in mafia family — [they] both are."

The mob family tree

While the Gambino family is arguably one of the best known mafia entities in the U.S. — because of the publicity that the now-late boss John Gotti received — they are only one of the several biggest in the country.

In New York City, there are five prominent families — Bonanno, Colombo, Gambino, Genovese and Luchese — that make up La Cosa Nostra, which the FBI describes as an "alliance of criminals."

The families are distinctly different with unique histories and members, but oftentimes they would dabble in similar criminal circuits which focus on: racketeering, drug trafficking, loan sharking, corruption, extortion and murder, among other things, according to the FBI.

"The 'Five Families' are not what they were, especially the Gambinos," said Boyce, adding, that the Gambino’s "profile in New York has been significantly reduced since John Gotti."

Beyond that, Boyce said that the various mob families are all facing competition on the drug trafficking front from outside their realm.

"Most of the heroin in this country comes from Mexico now — not from the mid-east, which the mob once controlled," Boyce said.

Looking for clues in Cali’s shooting

Joe Cantamessa, a retired FBI special agent in charge from the New York division’s special operations, was involved with a key mob boss case: he was responsible for installing the microphone in the home of Paul Castellano, the Gambino family boss whose assassination was orchestrated by his successor, Gotti.

The Castellano hit in 1985 prompted drama within the Gambino family, and Cantamessa said that such a blatant shooting of another Gambino leader — Cali — will prompt it’s own share.

"If a senior guy gets hit and if it's not a sanctioned hit, it's bad news for somebody," Cantamessa told ABC News.

"You’ve got to get permission to take out a 'made' member, somebody who's actually a member of a family," he said, noting that Cali fit that bill. "If anybody within the family or in a rival family steps outside the bounds then there would be consequences. It's all about permissions: nobody does anything to a made member without permission."

Law enforcement sources tell ABC News that shortly before Cali was shot he received something via his phone — either a call or a text — that lured him outside onto his front terrace on Wednesday.

Frankel, who was an agent on the FBI's Gambino squad in the late 1990s, said that whatever prompted Cali to step outside is going to be critical to the investigation.

"That’s a great piece of evidence, because whoever made that [call or text], unless it was a spoof [where the number is distorted], that's the person who drew him out," said Frankel, who now works as a contributor for ABC News.

"Because of the way he was shot and who he is — he’s a high ranking member of the Gambino family, he was shot 10 times on the street — it wasn't something that was hidden. Someone was definitely trying to say 'Franky’s dead and he deserved to die.' That’s the way I'm taking it," Frankel said.

Unanswered questions

While some of the optics of the latest hit seem to point to some obvious conclusions, there are still quite a few questions that investigators will have to tackle.

"Are they hitting him because he did something or are they hitting him to get rid of him? Did he go somewhere he shouldn't have gone? Did he go outside his crew or his family and cause trouble with another family?" Frankel said.

Past precedent seems to be an indicator for Boyce’s best guesses.

"This was probably a schism within this family, because that’s what history tells us," Boyce said, referencing the Gotti hit on Castellano.

Boyce also speculated that Cali’s family ties and possible subsequent actions could have been a factor.

Specifically, Boyce suggested that "old time mobsters, and 'Franky' Cali was brought up like an old school mobster" who value loyalty from family and people they can trust. That led Boyce to posit that Cali’s ties to the Sicilian mob through his wife could have led to him bringing in new crew members from Sicily.

"Is he bringing outsiders into the organization? Is there resentment that comes up from that?" Boyce said.