DETROIT (AP) — A judge has sentenced former Detroit Mayor Kwame Kilpatrick to from one-and-a-half to five years in prison for violating the terms of his probation on an obstruction of justice conviction.

Kilpatrick asked Judge David Groner (GRO-ner) to show him compassion during the Tuesday hearing. But Groner said “that ship has sailed.”

Kilpatrick was led from the courtroom in handcuffs.

Groner ruled last month that the 39-year-old Kilpatrick failed to report all of his assets and meet other conditions of his probation.

Kilpatrick was ordered to pay the city $1 million after pleading guilty in 2008 to obstruction of justice. Sexually explicit text messages showed Kilpatrick lied under oath about an affair with a staffer. He resigned, served 99 days in jail, agreed to give up his law license, repay the city $1 million, and stay out of politics for five years.

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After he was released from jail in February 2009, he found a job as a medical software salesman with Dallas-based Covisint. Since then, he has said he is working on his marriage and trying to be a better father to his three sons. He also has been making $3,000 monthly payments to the city of Detroit, saying he hopes to repay everything he owes.

But prosecutors contend he continues to lie — that Kilpatrick could afford to give more and has intentionally hid assets.

Groner agreed, saying Kilpatrick failed to disclose $240,000 in loans from prominent businessmen. He also said Kilpatrick failed to surrender nearly $23,400 in tax refunds and a share of cash gifts from two people.

The judge signaled that some time behind bars was likely when he told Kilpatrick on April 20 to get “your affairs in order.”

Wayne State University law professor Peter Henning told The Associated Press he expected Kilpatrick to get jail time, though probably less than what prosecutors requested.

“The former mayor hasn’t given the judge much of an alternative,” Henning said. “Once the judge found perjury, that was a sign this was going to be treated very seriously. It wasn’t an oversight. It wasn’t miscommunication. It was a lie.”

Defense attorney Michael Alan Schwartz wrote in his filing Monday that sending Kilpatrick to jail would merely inhibit his ability to pay the restitution.

“If the defendant were left to perform his employment functions without having to be taken away from his employment and without being subjected to procedures which interfere with his employment, the full restitution should be able to be paid within the next two years,” Schwartz told the judge. “Placing the defendant in jail will be of benefit to no one.”

It was not clear what impact jail time would have on Kilpatrick’s job at Covisint, a subsidiary of Detroit-based Compuware. Last year, Compuware Chair Peter Karmanos defended Kilpatrick’s hiring but warned further trouble could mean termination. He declined to comment Monday.

As of Friday, Kilpatrick had paid $139,223 toward restitution, according to Corrections officials.

Worthy said her office will help the city collect what it is owed.

“A receiver can also be appointed to chase down assets that defendant has hidden from this court,” Worthy wrote.

Copyright 2010 The Associated Press.