The shakeup happened just weeks after Edward Caban was officially named the city's new police commissioner.
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During the middle of the riot that broke out in Union Square last week, the NYPD announced the forced retirement of at least four top executives.
NYPD Chief of Detectives James Essig was one of the top police officials asked by Caban to submit his resignation last week. He has been with the department for four decades.
Several top officials were called, one by one, to meetings with Caban in his office at Police Headquarters, where they were told they would no longer be members of the NYPD's executive leadership last Friday.
"It's hard to really articulate what you're losing, what's walking out that door," said Former NYPD Chief of Detectives and ABC News contributor Robert Boyce.
Boyce noted that the chiefs survived the last change in leadership at the top when Mayor Eric Adams picked Commissioner Keechant Sewell. But with her sudden departure, and now a new top cop with a long history in the department, Caban was expected to choose some new leadership.
"And he's allowed to do that, however, there is some strategic risk here," Boyce said. "The chief of detectives is rarely touched at that point because they're in charge of so many things."
Paul DiGiacomo, the president of the Detectives Endowment Association, says the union has a solid relationship with the Essig, who led the detective bureau through a citywide drop in shootings and homicides -- with many cases solved.
Essig's Assistant Chief of Detectives Christopher McCormack was also asked for his resignation.
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"He is in charge of all the federal task forces and the state task forces that we fight crime on," Boyce said. "So, these are really strategic moves here."
Boyce says Chief of Transportation Kim Royster's exit may be the most surprising, but perhaps not, given her rank as a three-star chief.
"The higher you go up, the closer you get to the door, as they say," Boyce said. "And you know it and you know it going in every time there's a change in leadership."
Assistant Commissioner Gene Whyte was also among those asked to resign from their leadership positions.
"We owe them our deepest thanks," Caban said.
In a message sent Friday to all members of the department, Commissioner Caban said he was placing the right people into the right spots to do the right job for the people of New York City.
"I ask you to embrace these changes as we step into a future that is as bright as it is promising," he said. "I ask you to join me as we salute our departing colleagues, as they exit our privileged arena of public service with their heads held high. And I ask you to welcome the leadership team taking shape before us and to be fully confident in knowing we will all be better for the creative, dynamic, and forward-looking individuals at the top."
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On Monday, Caban announced the appointment of Tarik Sheppard as Deputy Commissioner of Public Information (DCPI) for the New York City Police Department.
A 19-year veteran of the NYPD, Deputy Commissioner Sheppard "brings a wealth of enforcement, investigative, and strategic management experience to this dynamic role," Caban's office said.
Caban was appointed to be the 46th Police commissioner of the City of New York on July 17.
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