Among the dozens of pardons and commutations former President Donald J. Trump issued before leaving office, one name has left some law enforcement officials reeling: Jaime A. Davidson, notorious in upstate New York for planning a 1990 robbery that ended in the murder of a police officer.

The commutation bypassed the typical federal process for seeking clemency, and was championed by an advocate who was herself granted a pardon in 2018. Experts said Mr. Trump’s decision to cut Mr. Davidson’s life sentence short was evidence of the problems that arise when presidential allies exert strong influence.

And after a re-election campaign that emphasized law and order, with rallies that sometimes featured the pro-police Blue Lives Matter flag, Mr. Trump’s decision was a baffling anomaly that upstate politicians, prosecutors and police union officials received with dismay.

“It’s hard to even put the reaction into words, you’ve got to grab a thesaurus,” said William Fitzpatrick, the district attorney of Onondaga County, and a friend of the officer. “But it’s just astonishment.”

But Mr. Davidson’s case is complex, and he was long championed by lawyers and relatives as a candidate for clemency. As the leader of a drug ring who helped plan the robbery of a rival, he was convicted of murder though he was not at the scene of the robbery that turned deadly; the man who fired the shot that killed Wallie Howard Jr., a Syracuse police investigator who was working undercover, has already been released.

And amid a national push to reduce incarceration rates that disproportionately affect Black men, some experts and advocates said the case was remarkable only because such decisions have been too rare.

“It’s not the grant itself that strikes me as inappropriate,” said Rachel E. Barkow, an expert on executive clemency and a law professor at New York University. “There are thousands of people like him and the real question is why him — as opposed to all of the people who are similarly situated.”

Executive clemency is aimed at showing mercy to deserving recipients, but Mr. Trump often used the power for personal or political goals. The majority of the sentences and convictions Mr. Trump wiped away in his final hours in office last week went to allies like Stephen K. Bannon or business executives and elected officials entangled in high-profile corruption cases.

Mr. Davidson, too, had ties to the Trump administration: His longtime lawyer was part of a team that represented Donald Trump Jr. in recent years. But of the 143 people granted clemency by the president last week, he was one of few who had been convicted in a violent crime case and the only one who had been connected with a murder.

The White House’s announcement noted that while in prison, Mr. Davidson “mentored and tutored over 1,000 prisoners to help them achieve their GED certificates” and “earned praise from prison officials for his dedication to helping others.”

It is unclear exactly what ultimately swayed Mr. Trump to grant clemency in a case that starkly differs both from most others he took on and his own tough-on-crime persona. But the unexpected decision was likely the product of several forces, including the influential advocacy of a former pardon recipient who retained close ties to Mr. Trump..

Thirty-one years ago, Mr. Howard was working undercover when he was fatally shot during an attempted robbery. The gunman and another suspect were quickly arrested, but Mr. Davidson was separately charged and later convicted in federal court after prosecutors argued that he led a cocaine ring in Syracuse and had concocted plans for the robbery.

Because Mr. Howard was killed during the commission of the robbery and in service of the drug ring, Mr. Davidson was convicted of murder and sentenced to life in prison. Mr. Davidson, who was not accused of being present at the scene of the shooting, has maintained his innocence.

Mr. Howard’s family could not be reached for comment on Tuesday. But in 2014, when a judge reduced the sentence of Robert Lawrence, the man who shot Mr. Howard, the officer’s mother and sister pleaded in court that it be reconsidered.

“My son didn’t get another chance,” his mother, Delores Howard, told Syracuse.com. “Why should he get another chance?”

The killing rattled the community and decades later, officers and friends still gather on anniversaries of his death.

“He probably would have been the first African-American chief someday,” Mr. Fitzpatrick said. “To have lost him that way just compounds the tragedy.”

After a chance encounter, a lawyer, Bettina Schein, took on Mr. Davidson’s case in 2004, but had little success in seeking reprieve. Years beforehand, the gunman recanted his testimony from trial and said that Mr. Davidson had not been involved — which the White House appeared to also cite in its explanation for clemency. (The man later reversed again, saying Mr. Davidson had in fact played a role, which the White House statement did not mention.)

Mr. Davidson had also twice made petitions to the Office of the Pardon Attorney in 2013 and 2017, according to federal records, but both had been turned down.

Then, as Syracuse.com first reported, appeals from family members to end his imprisonment drew the attention of an unexpected reader: Catina Johnson, the daughter of Alice Marie Johnson, an advocate who works to identify cases for clemency and had a direct line to the Trump White House.

“We have to help this man,” Ms. Johnson recalled her daughter saying in October.

After looking into the case herself, Ms. Johnson said she similarly began to believe in Mr. Davidson’s innocence, and became convinced that he was deserving of clemency.

“I’m certainly not saying Jaime was innocent of everything in life. But give this man a chance,” Ms. Johnson said in an interview. “He has more than paid his debt to society. Let him live free to do good in society, because he showed by what he did in prison that he’s going to be a change agent. I really believe in him.”

Ms. Johnson herself was the recipient of executive clemency from Mr. Trump in October 2018. After the reality television star Kim Kardashian West lobbied on Ms. Johnson’s behalf, the president commuted her life prison sentence for charges related to cocaine distribution and money laundering.

Since then, Ms. Johnson garnered influence with the former president, appearing in the Trump campaign’s Super Bowl television ad last year. She supported several of his final pardons and commutations, and though she has typically taken on nonviolent crime cases, she said Mr. Davidson’s “grabbed at her heart strings.”

Later in the fall, she said she shared her interest with Ms. Schein, who sent her a 62-page clemency petition. In the documents, which Ms. Schein was otherwise planning to send to the federal pardons office, she argued that a misidentification by the police, two false testimonies and pressure to solve the case led Mr. Davidson to wrongly spend 28 years in prison.

Over the next several months, Ms. Johnson continued looking into the case, she said, with the help and interest of Ivanka Trump and Jared Kushner, who also worked with her on several other clemency cases.

Then, on Sunday afternoon before the inauguration, Ms. Schein said her phone began ringing with an unexpected caller: the White House.

Both Ms. Schein and her husband, Alan Futerfas, have represented people from the Trump Organization, including Donald Trump Jr., in court over the past several years. Still, she said she was not fully sure whether Mr. Davidson would end up on the clemency list.

“I had to see it in writing because I couldn’t really believe it,” Ms. Schein said, adding that she believed Ms. Johnson’s connections to Mr. Trump played a greater role than her own in the commutation.

She added that her father was a police officer, and that she would not have represented Mr. Davidson — who differs from her typical slate of white-collar clients — if she did not believe his case was a “lamentable injustice.”

Mr. Davidson’s family members declined to comment through Ms. Schein, but she said several called her after the decision and were “so grateful for it.”

In Syracuse, law enforcement officials were confounded by the move. John Duncan, a former executive assistant U.S. attorney and the prosecutor in Mr. Davidson’s case, said he had not been contacted by the White House or Justice Department in the lead-up to Mr. Davidson’s commutation, as would have likely occurred had the petition gone through the Office of the Pardon Attorney.

But had he been, Mr. Duncan said he would not have agreed with the decision and noted that those misgivings did not extend to all his past cases. “If you ask me for a list of people who nobody should give a presidential commutation to,” Mr. Duncan said, “Davidson would pretty much be at the top of the list.”

Experts on presidential pardon and commutation practice questioned how thoroughly the White House reviewed the case and said the case reflected the undue influence the pardon process gives allies of the executive branch like Ms. Johnson.

“This is the kind of controversial case that courts are institutionally better suited to handle, keeping the president out of a political crossfire,” said Margaret Love, a former pardon attorney for the Department of Justice.

“We can’t operate a modern justice system with these antique, unfair and unreliable remedies. And pardon is indisputably one of them.”

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