UPDATE: Hundreds of Officers Stare Down Accused Cop Killer in Criminal Court

A 30-year-old wanted criminal with more than a dozen prior arrests, mostly for drug offenses, and 12 prior incarcerations allegedly shot a 33-year-old NYPD officer in the front of the head as he encountered the officer, who was responding to a report of gunfire near the FDR Drive in East Harlem, authorities say.

Tyrone Howard, also known as "Peanut," had three current warrants out for his arrest, including one on a second-degree assault charge, according to law enforcement sources. Authorities say they were looking for him in connection with a Sept. 1 shooting at the East River Houses. Police sources call Howard a "major drug player" and say he knew police were looking for him.

"The perpetrator involved here was obviously a hardened, violent criminal who should not have been allowed on the streets," Mayor de Blasio said Wednesday as he called for criminal justice reform.

Howard was most recently arrested in October 2014 on a drug-related offense and was jailed from that time through February of this year, when he was released into a drug diversion program, which is meant to keep drug offenders from overcrowding the city's jails.

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"If ever there was a candidate not to be diverted, it would be this guy," Police Commissioner Bill Bratton said. "There are people in our society who are criminals, who are violent criminals ... who should be separated from the rest of society."

Manhattan District Attorney Cy Vance said his office recommended state prison for the defendant and opposed his request for diversion.

Court officials said Howard qualified for the program because he was charged with selling and possessing drugs and was addicted.

Howard was allegedly part of a group that had engaged in a gun battle on an overpass near East 102nd Street and First Avenue around 8:30 p.m Tuesday. Officers on nearby rooftops who witnessed the gun battle radioed for backup and NYPD officer Randolph Holder and his partner were among those who responded, authorities said.

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Howard fled the site of the gun battle, stole a man's bicycle at gunpoint near 126th Street and started riding that bicycle near the promenade, authorities allege. As Holder and his partner scoured the area for potential suspects, they encountered and followed three individuals but soon realized those individuals had nothing to do with the gun battle and continued heading down a walkway.

As they walked down that path, Howard approached the duo on his bicycle, authorities say. According to Bill Aubry, Manhattan chief of detectives, Howard saw the officers, put down his bike, pulled out a gun and fired once, striking Holder in the front of the head. Howard then headed toward Holder's partner, who pulled out his own weapon and fired at Howard, striking him twice, including once in the leg. Howard fled north on the promenade and was apprehended by other officers.

Holder was taken to Harlem Hospital in very critical condition Tuesday night and later pronounced dead. Dozens of Holder's fellow officers stood outside the hospital and saluted as the ambulance carrying their fallen colleague left. Afterward, many embraced one another.

Bratton, reflecting on the deadly police shootings he has seen over the course of his career, says coping with the losses never gets easier.

"It never gets easier. I'll be very frank with you -- it gets worse each time," Bratton said Wednesday, reflecting on the police deaths he's seen over the last 45 years. "Last night was one of those nights -- it was not easy to do."

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Bratton spoke about a time in the 1970s when dozens of officers went down every year.

"The challenge for all of us is in the midst of all of our well-intended efforts to deal with racial issues, to deal with criminal issues, narcotics issues, is that we don't let the insanity again take hold of us," Bratton said.

Howard was released from the hospital into police custody Wednesday, according to Bratton. Police sources said he faces charges of first-degree murder of a police officer and second-degree robbery for the bike theft.

There was no immediate information on whether Howard had an attorney.

At least one gun was recovered at the scene of the gun battle, law enforcement sources said, and authorities believe at least three weapons were used. Police say the murder weapon has not yet been recovered, but that witnesses saw the suspect toss something toward the river as he ran from the officers. They believe the gun is in the water, and NYPD officials say they're confident the weapon will be recovered since the river is shallow at the edge.

The FDR Drive remained closed in both directions between 96th Street and 125th Street for more than 12 hours before it was reopened shortly before 1 p.m. Wednesday as investigators scoured the scene.

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At a news briefing Wednesday, de Blasio said the tragic shooting should underscore a desperate need for stricter gun laws.

"Our officers do so much every day to protect us and yet they grapple every day with an unrelenting flow of firearms into this city from the outside," de Blasio said.

Holder, a native of Guyana, had five years on the job and worked in the anti-crime unit of PSA no. 5, a command that polices public housing developments in East Harlem and Harlem, according to Bratton.

His father and his grandfather were both police officers in Guyana, and Holder joined the NYPD after he moved to New York.

Speaking outside his home Wednesday, Holder's father said his son has always wanted to be a policeman. He described his son as an easygoing, loving young man who did his duties diligently and with pride.

He also said he had just taken the detective's exam and was looking to move up in the force.

"In each job I think there's danger, no matter the type of work you're doing. There's some kind of risk involved," Randolph Holder Sr. said. "If I had known that was the last time, I would have told him not to go out for duty. If I had known ... stay home."

Holder's body was transported Wednesday to the Jeremiah C. Gaffney Funeral Home in Inwood, Long Island, not far from his family's home in Far Rockaway. A line of blue greeted the convoy there.

A wake will be held for Holder at the Greater Allen A.M.E. Cathedral of New York in Jamaica, Queens on Oct. 27, and his funeral will be held the next afternoon in the same church, according to police. He will be buried in Georgetown, Guyana.

JetBlue said it would offer free flights to police officers who wanted to attend.

De Blasio said Holder had an "exemplary record" as a police officer. He ordered all flags in the city be lowered to half-staff in Holder's honor and called for solidarity in the wake of this tragedy. The Empire State Building was also to be lit in blue at sunset Wednesday in Holder's honor.

"Our hearts are heavy and we offer our thoughts and our prayers to his family, who are experiencing unimaginable pain, as we saw earlier when we gathered with them," he said Tuesday, calling Holder "an immigrant who wanted to give back to his city and to his country, who had an exemplary record as a police officer, who did everything the right way."

Bratton especially offered condolences to Holder's father, "who in his time of grief sought to comfort the officers from PSA 5. He was strong enough and brave enough to go in and address them. As they tried to comfort him, he in fact was comforting them."

Holder is the fourth NYPD officer killed in the line of duty in the last 11 months. Brian Moore, 25, was shot in the head while sitting in an unmarked patrol car in Queens last May; he was taken off life support two days later. Rafael Ramos and Wenjian Liu were shot in the head as they sat in their patrol car in Bedford-Stuyvesant in December 2014, days before Christmas.

Before the slayings of Ramos and Liu, the NYPD had gone two years without an officer dying in the line of duty.

"New York City police officers every day go out and carry themselves like superheroes but the reality is when we're attacked we bleed, when we bleed we die and when we die we cry," Patrolmen's Benevolent Association President Patrick Lynch said.

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