Jeffrey Bennett's pleas for mercy Tuesday in a Minneapolis federal courtroom sounded like a country song.

The 52-year-old resident of Lakeland, Tenn., admitted at his sentencing hearing that he'd made serious errors when he got involved in a plan to embezzle nearly $400,000 from a Minnesota trucking company, launder the money and evade his federal income tax obligations.

That's where most white-collar criminals stop. Not Bennett, who fired his lawyer after his conviction last year. He called upon several friends, who spoke eloquently about his family ties and how he had supported them when times got rough.

But Bennett's own words and voluminous court filings backfired as he blamed his former boss, a difficult childhood, a bad breakup, his own lawyers -- and even a driver who ran over his dog -- for what U.S. District Judge Patrick Schiltz called a history of financial crimes dating back to his late teens.

"Everyone, it seems, has done Mr. Bennett wrong," Schiltz said soberly as he imposed an eight-year prison term over the sniffles of Bennett's friends and relatives.

Bennett was convicted in December of mail fraud, conspiracy to commit mail fraud and money laundering, and tax evasion. The crimes stemmed from an elaborate phony invoice and kickback scheme that defrauded his former employer, Eagan-based Advantage Transportation, a freight logistics company.

Schiltz ordered Bennett to repay the firm $393,183.37, noting his former boss, Clayton Hogeland, would also be liable for the restitution when he comes up for sentencing.

Bennett and Hogeland ran the scheme from 2003 through April 2005. Hogeland, 42, now living in Aurora, Texas, had been the company's general manager and hired Bennett as sales manager for the company's Tennessee office.

The 'real' Jeff Bennett

Bennett submitted bogus invoices from four shell companies for Hogeland's approval. Bennett kept about two-thirds of the cash and kicked back the rest to Hogeland in checks made out to him and his wife, Jennifer, 39.

Several of Bennett's friends said he deserved a break. "He's a good man, and sometimes good men do something unthinkable," said Verdell Jones Jr. of Champaign, Ill. "Jeff Bennett is a caring individual who'd give you the shirt off his back."

Bennett said he could get 20 more people to make similar testimonials and asked for probation or an alternative to prison, such as location monitoring. "My family needs me, and my goal is to pay the restitution and fines," he said.

But Assistant U.S. Attorney Timothy Rank asked for a sentence of 108 months, the top of the federal guidelines range. "This is not, your honor, an isolated incident of bad judgment," Rank said. "It is who the defendant is."

Repeated convictions

Schiltz agreed, and sentenced Bennett to 95 months in prison followed by three years of supervised release. Bennett's claim that he was duped by Hogeland is "preposterous," said Schiltz, who presided over their trial.

"This is, in fact, Mr. Bennett's 11th conviction and fifth felony conviction. All involved stealing," Schiltz said, yet he argues that he has "virtually no criminal history."

Bennett fired back. "You make me out to sound like I'm some major criminal, like Al Capone or something," he said. "This court does not know the real Jeff Bennett."

Dan Browning • 612-673-4493