The NY Times reports that the police had gone looking for Tyrone Howard at least 10 times since Sept. 1, when, investigators believe, he rode up to a rival just after midnight and shot him. But 10 times he eluded them.
When officers finally did encounter Mr. Howard on Tuesday night, fleeing from the scene of another shooting in the same Upper Manhattan housing project, he was armed, the police said.
He was riding a stolen bike and concealing a .40-caliber handgun, the police said. As two plainclothes officers approached, he wheeled around, dropped the bike and fired one shot into the forehead of one of the officers, Randolph Holder, the police said.
“It was quick,” a senior police official said. “He swung around, on the bike path; he was on the bike and he just jumped off and ‘Boom.’ Quick. No words.”
Officer Holder’s partner, Omar Wallace, fired back, striking the assailant as he fled north along Franklin D. Roosevelt Drive. He was arrested near 125th Street beside the churn of the darkened East River where, soon after, police divers recovered a .40-caliber magazine that had been tossed into the waterway.
The fatal shooting, the fourth of a New York City officer in 10 months, was an outgrowth of what officials called one of the city’s most intractable law enforcement challenges — the persistent violence stemming from so-called crews, small bands of young men often allied with a particular housing project or neighborhood and locked in frequently bloody rivalries
Mr. Howard, 30, was charged with first-degree murder and robbery. At a packed arraignment in Lower Manhattan late Wednesday night, a judge ordered that Mr. Howard be held in jail without bail. Well over 100 police officers attended the hearing, as did members of Officer Holder’s family. At times people shouted obscenities at the defendant.
Mr. Howard was believed to be among those sowing violence across a pocket of East Harlem, several men whose images and gang affiliations hang in police precinct roll-call rooms and whose faces are known to anticrime unit officers, like Officer Holder, 33, whose assignment includes confronting the most violent criminals.
Indeed, one of the ways Mr. Howard knew the officer approaching him on a darkened pathway of F.D.R. Drive — besides by the silver shield dangling from his neck — was that they had encountered each other before, the police said. Mr. Howard had 23 arrests as an adult, including one in connection with a shootout in June 2009 on a basketball court in the East River Houses that wounded two bystanders: an 11-year-old boy and a 77-year-old man. (The case did not go forward, officials said, because prosecutors were unable to present any witnesses who could identify Mr. Howard.)
Although he was one of 19 defendants in a roundup of alleged crack-cocaine dealers last October in the East River Houses, where he lived, publicly available court records show no violent felony convictions in his history. The 2009 shooting was sealed, officials said. And, rather than jail, Justice Edward J. McLaughlin of State Supreme Court in Manhattan diverted his case in December to a special court where he was eventually ordered into drug treatment, a decision that both Mayor Bill de Blasio and Police Commissioner William J. Bratton denounced on Wednesday.
“If ever there was a candidate not to have been diverted, it would be this guy,” Mr. Bratton said.
A spokesman for the state court system, David Bookstaver, disagreed, saying the case of Mr. Howard — a repeat drug offender who also used drugs with no admissible history of violence — was exactly the sort that diversion by a judge was intended to address. “There would be no reason to have that judicial authority,” Mr. Bookstaver said, “if all the cases were easy.”
The killing of Officer Holder and the ensuing discord over the handling of Mr. Howard’s most recent drug case highlighted the tensions playing out in the criminal justice system as calls grow to reduce the number of people behind bars and officials try to navigate a potent and emotional debate. Mr. Bratton had been scheduled to stand with 130 law enforcement leaders in Washington on Wednesday to call for changes to reduce the nation’s incarceration rate, and to meet with President Obama on Thursday.
Instead, on Wednesday afternoon, Mr. Bratton stood at Police Headquarters and in an emotional news conference, alongside Mayor de Blasio, sought to reconcile the movement to roll back damaging criminal justice policies with the killing of a local officer by a man who, they said, had benefited from an earlier reform effort that eased the state’s Rockefeller drug laws.
“Even as we’re attempting to find balance,” Mr. Bratton said, “it’s unfortunate that there are people in our city and our society that, despite our best efforts, that are going to be criminals and many of them are violent criminals and we need to separate them from the rest of us. And this individual I think is one of those.”
The killing again plunged the Police Department into mourning. Ten months to the day, on Dec. 20, two uniformed police officers — Wenjian Liu, 32, and Rafael Ramos, 40 — were ambushed in Brooklyn. The suspect in that shooting, Ismaaiyl Brinsley, committed suicide in a subway station.Officer Brian Moore, 25, died in May, two days after he was shot by a gunman who fired into his patrol car. The suspect, Demetrius Blackwell, 35, has been charged with first-degree murder, attempted first-degree murder and other crimes. He has pleaded not guilty.
In an interview after Officer Holder’s shooting, Justice McLaughlin noted that Mr. Howard had never been convicted of a violent crime as an adult, though court records show that the judge was aware of a sealed juvenile conviction for robbery, and that the prison sentences he had served for drug possession and sale had done nothing to keep him from breaking the law over and over.
Justice McLaughlin said he also took into account a social worker’s report, submitted by the defense, that said Mr. Howard was a child of addicts who had been hooked on PCP since he was a teenager. The report said that Mr. Howard’s arrests had all stemmed from his addiction and that he would benefit from treatment.
“When I get out, I go back to PCP and I know I have to break that cycle,” Mr. Howard told a social worker, according to the report. He was working in construction in Rye, N.Y., at the time of his October 2014 arrest.
Justice McLaughlin said he also received a long letter from the mother of Mr. Howard’s child, who begged for leniency. “When you get a robe, you don’t get a crystal ball,” the judge said, adding that he had considered the national conversation around drug sentencing. “Diversion is a good thing. It has a lot of support.”
The Manhattan district attorney, Cyrus R. Vance Jr., said he had opposed the request for diversion but respected the judge’s decision.
Over the summer, Mr. Howard stopped taking part in the drug treatment program, the officials said. A warrant was issued on Sept. 17 after he failed to show up for court.
On Tuesday around 8 p.m., Officers Holder and Wallace were patrolling near 120th Street north of the East River Houses. Five years into a promising police career, including six commendations, Officer Holder, an immigrant from Guyana, had begun telling relatives of his growing sense of the dangers of the job he loved.
There have been seven murders so far this year in the housing projects patrolled by Officer Holder, up from four at this point last year, and an increasing number of people shot.
At 8:30 p.m., officers on a public housing rooftop heard shots and saw two groups of men exchanging gunfire on East 102nd Street below them, Deputy Chief William Aubry, the head of Manhattan detectives, said. Officers converged as suspects fled in different directions.
One took off on foot down First Avenue. Others ran across the highway and down by the East River.
A witness told the police that his bicycle had just been stolen at 106th Street and the promenade by a man with a gun. A call went out: Be on the lookout for a suspect, possibly armed, on a bicycle, riding north along the promenade by the river.
One police unit moved north from 96th Street. Officers Holder and Wallace began moving in from 120th Street, where there is a footpath over F.D.R. Drive, Chief Aubry said.
As the officers descended the footpath ramp to the promenade, “Tyrone approaches them on the bicycle,” Chief Aubry said, and pulls a gun. A single shot in “the front of the head,” the chief said.
Officer Holder was taken to Harlem Hospital Center and declared dead at 10:22 p.m.
Treated for gunshot wounds to a leg and the buttocks, Mr. Howard was later taken to the 25th Precinct station house on Wednesday to stand in lineups — for the shooting and the bicycle theft — as detectives combed through video and physical evidence.
Detectives were also looking to charge him in the Sept. 1 shooting, in which, police officials said, Mr. Howard had gone after a member of his own crew, the East Army, whom he deemed a rival. The man, 28, was hit three times in the shooting but survived, and later named Mr. Howard as the gunman, the police said.
The police believe the initial shooting on Tuesday in the housing project might have been retaliation for that earlier episode.
In the 19-defendant drug case, Mr. Howard was never charged with conspiracy, and prosecutors said he was believed to have been a small-time operator, selling drugs on his own in the housing projects and sometimes coming in conflict with other groups.
“He was driving crime, but he wasn’t an East Army gang member as we saw it,” said one senior prosecutor, who spoke on the condition of anonymity because the investigation was continuing. “More of a lone drug seller.”