He went to prison for attempted murder and robbery, expecting to spend the rest of his life behind bars.

That did not stop his ambitions, prosecutors said.

On Friday, a new indictment accused the man, Howard Smith, of leading a murderous New York street gang from inside a maximum-security prison in upstate New York, where he had been incarcerated since 2004.

The indictment said Mr. Smith, 49, would give orders through prison phone calls, including once directing a gang member to carry out an act of violence last year, saying anyone who disobeyed the order would be kicked out of the gang.

In conversations intercepted by prosecutors, he called himself “the godfather.”

He expected gang members to show their loyalty by sending him their drug proceeds, prosecutors said, allowing him to rack up $25,751 in his prison commissary account.

Mr. Smith is accused of running a violent drug-dealing gang called the Brick Squad, a subset of a larger criminal organization that is part of the Bloods. The group operated primarily in Brooklyn in the neighborhoods of Bedford-Stuyvesant, Brownsville and Brooklyn Heights, but they also sold drugs in Binghamton, N.Y., and Bangor, Maine.

Nine other defendants were indicted along with Mr. Smith, including another gang member who was already incarcerated and accused of ordering a murder from prison.

The Brooklyn district attorney’s office, which filed the indictment, said the case highlighted gaps in oversight in New York’s state prisons.

“It is one of the most disturbing aspects of this case,” said Eric Gonzalez, the Brooklyn district attorney, “that they’re harming our communities while they’re still in custody.”

In particular, the indictment raised questions about how an inmate with such a high-dollar commissary account had not been flagged earlier.

There are currently no limits to how much money inmates can have in their commissary accounts, Mr. Gonzalez said, adding that he will refer the matter to the New York State Department of Corrections.

Thomas Mailey, a spokesman for the department, said, “The department has zero tolerance for illegal activities being conducted in state correctional facilities and has fully assisted with the ongoing investigation.”

Mr. Smith called his underlings through the regular prison phones that inmates were allowed to use, not through a contraband cellphone, prosecutors said, and one way he circumvented the rules was by registering his calls to another inmate’s pin number.

Prosecutors said the Brick Squad was unusual from a typical street gang, which is often a disorganized group of young men who grew up on the same block. The Brick Squad adhered to a strict constitution with a clear leadership; they showed their loyalty through hand signs, clothing and music lyrics.

The gang paid close attention to the members moving up and down within the hierarchy, known internally as the “Forbes” list, the indictment said. Two of the defendants discussed selling heroin in Atlanta to prove to Mr. Smith that they were worthy of a promotion.

After one gang member was promoted, he called a friend in prison and said, “There’s mad discrepancies going on with the Forbes,” according to prosecutors.

Gang members had to memorize an elaborate coded language that would allow the phone calls from prison to go undetected. Anyone listening in would be thoroughly confused.

Investigators were able to crack the code when they found handwritten sheets of paper that detailed the secret language. For instance, cocaine was “A-Rod,” and heroin was “home invasion.” Gang members referred to people suspected of cooperating with law enforcement as “college dropouts.” Guns were often called “duffles.”

The indictment charged the gang with carrying out two murders near Bedford-Stuyvesant. One of the victims was a Brick Squad member himself. He was gunned down in December 2017 when the gang had mistakenly believed he was cooperating with law enforcement. The other, a member of a rival family, was shot and killed in April 2018 after a long feud.

Both murders were captured on nearby surveillance footage.

After one of the murders, the indictment said, Mr. Smith promoted the two men who handled the killing.

Prosecutors said the gang made hundreds of thousands of dollars a year selling illegal drugs, including heroin laced with fentanyl.

In a recorded conversation, one defendant said the heroin he brought from Brooklyn to sell in Maine was responsible for three overdose deaths. He discussed wanting to switch to selling crack cocaine — “I was scared, bro,” he told another gang member — but said the heroin was too profitable, according to the indictment.

Despite wielding tremendous power behind bars, Mr. Smith appeared to be lonely at times. He complained that gang members were not visiting him frequently enough and said that he wanted them to “take care of me.”

In a phone call recorded by prosecutors, he lamented, “Nobody come see me.”

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