The man accused of murdering a New York City police officer Tuesday night had been arrested 28 times since he was 13, according to police, leading to questions about why he was let out of jail for a drug treatment program.

Tyrone Howard, 30, who is accused of stealing a bike and shooting Officer Randolph Holder in the head after a chase Tuesday night, was arraigned late Wednesday in Manhattan Criminal Court. He did not enter a plea after being charged with first-degree murder and robbery and was ordered held without bail.

Police said he had been arrested in connection with a 2009 shooting that injured an 11-year-old and a 78-year-old.

Manhattan Supreme Court Justice Edward McLaughlin told the New York Post he was unaware Howard was a suspect in the 2009 shooting when McLaughlin ordered him to be sent to the so-called "diversion program" last year. The Post reported that McLaughlin did so over the objections of prosecutors, who pushed for a six-year prison sentence after Howard was arrested along with 18 other people and charged with selling crack cocaine to an undercover officer at a public housing complex.

"I know I made the right decision. I don’t get a crystal ball when I get a robe," McLaughlin said. "If I wanted to avoid being in the papers I could probably accomplish that by doing nothing but [make] decisions designed to give myself cover and excuses."

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New York Police Commissioner William Bratton said Wednesday that Howard was a "poster boy for not being diverted." Mayor Bill de Blasio added, "someone like this shouldn't have been on the streets."

Assistant District Attorney Linda Ford said the case against Howard would be presented to a grand jury on Friday and Monday. His attorney, Brian Kennedy, did not ask for bail and said he wasn't sure yet if his client would testify before the grand jury.

Howard, who has two children, was bailed out of jail in February of this year, pleaded guilty to the drug charge, and was making regular court appearances until late August, when he skipped a court date, court system spokesman David Bookstaver said. A lawyer who represented Howard in the recent drug case, Robert Levy, said his client was trying to get into a residential treatment program before he skipped his court dates.

Days later, Howard shot and wounded a gang member, police said. Investigators had made 10 unsuccessful attempts to arrest him at various addresses before Tuesday's shooting.

"It's unfortunate that there are people in our city, in our society, that, despite our best efforts ... they're criminals," Bratton said. "And this individual, I think, is one of those."

At his arraignment, Howard wore a white jumpsuit and appeared to slouch down during the proceeding. Kennedy, his defense attorney, said Howard had been suffering from chest pain.

"There's a lot of details we don't yet know in this tragic event," Kennedy said. "We don't know Mr. Howard's involvement. We don't know if there was a gun recovered. There's a lot of missing details."

Several of the officer's family members also were in the courtroom sobbing. Some shouted at Howard during the proceeding.

"Once you met him, you loved him," Holder's cousin, George Johnson, said. "He was respectful. There was nothing not to like about him. Everything about him was good."

Holder, a five-year veteran, made 125 arrests in his career and was awarded six departmental citations for his work. The Guyana native, 33, was the son and grandson of police officers and worked in a division that polices public housing developments.

Holder is the second New York Police Department officer killed in the line of duty this year and the fourth in the past 11 months. But while line-of-duty police slayings are down from a high of 12 in 1971, the four officers killed in the past 11 months represent more than in any 12-month period in recent years, police records show.

Holder and his partner had responded to a report of shots fired near a public housing development in East Harlem Tuesday. When they arrived, a man said his bike had been stolen at gunpoint and the thief fled with a group of people along a footpath near the East River.

The officers caught up to a man with a bike on a pedestrian overpass that spans a highway and traded gunfire, police said. After Holder was shot, the gunman ditched the bike and fled, police said. He was caught several blocks away with a gunshot wound to his leg, Bratton said.

The Associated Press contributed to this report.

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