When former New York City police commissioner Bernard Kerik -- who once ran the Big Apple lockup Rikers Island -- walked into a federal penitentiary as a prisoner in 2010, it was, he said, like "dying with your eyes open."
"Your entire life as you knew it moves on around you, and there isn't a damn thing you can do about it," the recently released tax and obstruction convict said last week. "Your kids grow. ... The house changes. My dog died. My brother-in-law died."
At the Federal Correctional Institution Cumberland, in Maryland, where he served his sentence, he lived among the kinds of people he spent his life locking up. That's what former Pittsburgh police chief Nate Harper could face following his sentencing, set for Tuesday.
Mr. Harper's fate is in the hands of U.S. District Judge Cathy Bissoon, who rose to that post in late 2011 after three years as a magistrate judge. She faces a decision in which she must weigh Mr. Harper's history, his precise role in the conspiracy to commit theft and the importance of deterring others from similar dips into the public cookie jar.
Though federal guidelines suggest a sentence of 1 1/2 to two years, she can go as low as probation or as high as five years.
"It comes down to a very difficult call for a judge," said Bruce Antkowiak, a former federal prosecutor and now a law professor at Saint Vincent College in Latrobe. "The strongest cards [Mr. Harper's attorneys] have to play are his history with the department, the decades of work he has put in, the numbers of other people from law enforcement who evidently respect him."
Those same factors, though, could count against him.
"Either you think this is a fundamentally decent guy who did something wrong, or you think this is a public official who should be held to another standard," said Wesley Oliver, the Criminal Justice Program director at the Duquesne University School of Law.
Mr. Harper could argue that his lawman background puts him at risk in prison. The U.S. Supreme Court found in the case of police sergeant Stacey Koon, sentenced to prison in the beating of Los Angeles motorist Rodney King, that judges can give lighter sentences to defendants who are "unusually susceptible to prison abuse."
In the recent case of former corrections officer Arii Metz, though, prosecutors countered that argument by showing that the federal prisons already house many former police in relative security. As of last month, there were 1,269 former law enforcement officials in federal custody, according to the Bureau of Prisons.
"There are guys who are going to hate him because he was a cop," Mr. Kerik said. "There are going to be guys who are going to respect him because he was a cop."
Mr. Harper pleaded guilty in October, confirming that he failed to file tax returns for four years and diverted $70,629 in public funds into an unauthorized credit union account and spending $31,987 on himself.
The prosecution has maintained that Mr. Harper told two civilian subordinates to open and handle the account, making him a supervisor in the conspiracy, and subject to a harsher sentence.
The defense has countered that Mr. Harper had no co-conspirators, but also that the unauthorized account wasn't his idea. They haven't yet named the alleged mastermind.
"The government's response is going to be: Who cares?" Mr. Antkowiak said. "When you admit that you told two city employees to open these accounts and draw the Visa cards on them, you're a supervisor" of the crime.
Mr. Harper met with federal investigators "approximately 10 times," according to his attorneys. There's no indication, though, that the prosecution will ask the judge to impose a lighter sentence for what's called "substantial cooperation."
"We don't know what happened in those 10 meetings," Mr. Oliver said. Nor is there any indication of any results, he said, noting that a key part of weighing a defendant's cooperation is "how many busts, how substantial the busts were."
The flip side: Two defendants -- both of whom were given credit for cooperation -- publicly blamed Mr. Harper for a separate bid-rigging scheme in hearings before Judge Bissoon. The former chief has never been charged in relation to the incident, a contract won by Alpha Outfitters -- a company controlled by the chief's long-time friend -- to install and maintain computers and radios in police cars.
The judge shouldn't give much weight to their accusations, Mr. Oliver said, though he noted that the charge "tends to tear down the narrative that the defendant is trying to tell" about a good man with a bad debit card.
With the eyes of the public, and especially of law enforcement, on the case, the judge may carefully weigh the deterrent effect of the sentence.
"Look, one of the things a judge always considers is what kind of message [she's] sending with this sentence," said John Burkoff, a law professor at the University of Pittsburgh. " 'What's the message I'll be sending to police officers who may be tempted to do something bad if I'm lenient?' "
Mr. Kerik, now an advocate for sentencing reform, suggested that the message has already been sent. It could be amplified, he said, if the judge gives Mr. Harper probation but orders him to speak to police recruit classes about his crime and punishment.
"They're going to take his pension," Mr. Kerik said. "You've taken his reputation. He's now a convicted felon. He's going to have legal fees he'll have to pay for.
"That guy has been destroyed."
Rich Lord: email@example.com, 412-263-1542 or on Twitter @richelord.