As New York City enters the sixth day of protests over police violence and the killing of George Floyd, Mayor Bill de Blasio is facing one of the biggest challenges of his mayoralty: controlling a city exploding with outrage amid the backdrop of a pandemic.

Following the arrests of nearly 700 people on Monday night, many are wondering whether the NYPD can stop the looting and vandalism that have followed the protests. Although the city implemented a rare curfew at 11 p.m. on Monday, looting and vandalism was still rampant and, in some cases, happened as NYPD officers appeared unwilling to intervene.

In response, de Blasio announced that Tuesday's night curfew will begin at 8 p.m.

Adding to the chorus of detractors, Governor Andrew Cuomo on Tuesday criticized de Blasio and the NYPD for failing to handle the situation with its outsized police force.

“The NYPD and the mayor did not do their job last night," Cuomo said. "Look at the videos, it was a disgrace. I believe that. I believe the mayor underestimates the scope of the problem, I think he underestimates the duration of the problem, and I don't think they've used enough police to address the situation. It's inarguable that it was not addressed last night. Facts, right? This is a glass of water."

In response to the governor's remarks, Freddi Goldstein, the mayor's press secretary, issued the following statement: “These comments are offensive to the men and women of the NYPD, who are out there every night trying to keep New Yorkers safe. It would be nice if our officers knew they had the respect of their Governor.”

Some elected officials have called on the mayor to bring in the National Guard, who are on standby.

But speaking defiantly at his press conference, de Blasio attributed the looting to a "small group of criminals" and accused the press of trying to "mischaracterize reality."

"I saw police officers trying to deal with a very difficult situation," he said.

He also firmly pushed back against bringing in the National Guard.

"The National Guard should not be brought here," he said. "We have 36,000 police officers."

Cuomo has said he has offered all the mayors in New York state the services of the state police and National Guard. But he has stopped short of using this authority under a state of emergency to bring the National Guard in, saying that it would effectively "displace" de Blasio.

"I don't think we are at that point. That would be such a chaotic situation in the midst of an already chaotic situation."

He later added: "I believe the NYPD can do this."

New York City mayors have long been judged on their performance during times of civil unrest.

The example held up most often by political historians is when Mayor John Lindsay, a liberal Republican who served for two terms during a time of racial, social and economic unrest. In 1968, as uprisings erupted in cities across the country after the assassination of Martin Luther King Jr., Lindsay elected to walk the streets of Harlem and other black neighborhoods, in his shirtsleeves, talking with and consoling residents as only one NYPD detective stood beside him.

In the wake of Lindsay's outreach, New York City had minimal looting and violence compared to other cities, which went up in flames and required the assistance of active-duty soldiers to quell the violence.

"He got a great deal of credit," said George Arzt, the press secretary to Mayor Edward Koch and a longtime political observer. "He calmed down the rioting."

By comparison, de Blasio has tried to straddle a line between defending police officers and expressing solidarity with the demonstrators. Although he has not joined the protests, de Blasio has toured several neighborhoods. On Tuesday, he recounted his conversations with New Yorkers in recent days.

"They're frustrated. They're worried. They're worried about their health. They're worried about their children's health," he said. "People talked about their lives and there's such pain and frustration, and people have been cooped up for months. This is a horrible, perfect storm we're living through, but we are better than some of what you see, we are better than this crisis."

Arzt said that given the chastising from Cuomo, Tuesday night will be a critical test for de Blasio.

"I’m sure for the mayor the walls are closing in," he said, adding that he would have advised the mayor to allow some members of the National Guard to be strategically positioned in shopping districts.

Arzt said one of the missteps the city made was setting Monday's curfew so late. Most of the looting has occurred once darkness falls.

"Even my mother said you got to be in by 10 p.m. when I was little, sometimes 9 p.m.," he said.