In a letter to U.S. District Court Judge Freda Wolfson, a man who was crowned Pimp of the Year wrote about the times when he and the prostitutes working for him "bonded as a family."
Wolfson, who was asked Friday to consider sentencing Matthew Thompkins to the minimum terms of 10 years, wasn't buying it.
"You wouldn't send your sister or your daughter out to do that," she said. "That's no family."
The judge instead gave Thompkins more than 23 years - nearly the maximum sentence.
Thompkins, a 38-year-old native of the Bronx, N.Y., ran a sophisticated prostitution ring for 15 years, operating out of New York City, Atlantic City, Las Vegas, Philadelphia and other cities, prosecutors said.
For much of that time, he worked a day job as a letter carrier.
He had a $325,000 home in Galloway Township, N.J., where the girls and young women in his "stable" stayed while working in Atlantic City.
Thompkins was arrested in 2005 in a nationwide operation called "Innocence Lost" that targeted pimps who prostituted underage girls. The complaint against Thompkins cited one girl who said she started working for him when she was 14.
During the raids, investigators found two trophies proclaiming Thompkins "Pimp of the Year," including one topped with a figure in a cape and a crown, holding a scepter. An annual gathering of pimps known as the Players Ball, where the Pimp of the Year trophy is handed out, has been chronicled, notably in the 1999 documentary American Pimp.
Thompkins also gave a daylong interview to a writer from the Florida-based hip-hop magazine Ozone shortly before his arrest. In the December 2005 edition of the magazine, a pimp known as "Brandon" - one of Thompkins' aliases - drives around Las Vegas in a white Range Rover, holding forth on his "pimptuition."
"Brandon believes that anyone who pimps a woman under 18 deserves to go to jail," the article said.
Prosecutors cited the article Friday as an example of Thompkins' brazeness. The pimp was far less effusive in court, when he apologized in a halting voice for his "life of crime."
"It's hard to speak right now," he said. "I know a lot of people were affected by my decisions, and I knew better."
Thompkins' business was extremely profitable. He has agreed to forfeit four homes, eight vehicles, and nearly $750,000. Prosecutors said his prostitutes were forced to turn over all their money - usually by converting cash into U.S. Postal Service and Western Union money orders - while they were paid just $20 a day.
Wolfson, sitting in Trenton, also yesterday sentenced Demetrius Lemus, whom prosecutors described as an "associate pimp." Lemus, 37, of the Bronx, got 96 months in prison.
Five other women who worked for Thompkins have pleaded guilty and are awaiting sentencing, including one woman who had two children with him.
The attorney for one of those women, Kemyra Jemerson, has filed a document with the court saying she might have been suffering from Stockholm syndrome, a condition in which captives come to bond with their tormentors.
In any case, Jemerson, who was recruited to work as a prostitute at 16, reported horrific abuse, including being beaten with a metal chain for buying marijuana.
"Brandon" also told the Ozone writer that his prostitutes were free to leave at any time. Melissa Smith, one of them, would disagree.
She told the court Friday that she was recruited into Thompkins' stable when he promised to get his "lawyer friends" to help her win back custody of her son. After she fled the stable, Thompkins promised her she could come back without recrimination.
"Instead, he beat me with a copper pipe," she said. "When he says you can come and go as you please, that's a lie."
About two dozen family members attended Friday's hearing and wrote letters on Thompkins' behalf. They described a far different person - a good father, brother and friend who was hard-working and responsible.
A cousin, Melody Glover, spoke for the family, identifying herself as a lawyer in New York.
"We just want the court to know that we love him, we support him," Glover said. "We know in our hearts that when he's released from prison, he'll be a productive member of society."
Smith doubted that as well.
"If he gets out, I know he'll do it again," she said. "That's all he ever talks about - pimping and ho-ing."