Dennis Hastert pleads guilty, faces up to 6 months in jail

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Dennis Hastert faced a federal judge Wednesday and admitted in a quiet voice that he broke the law, cementing a harsh legacy for the longest-serving Republican speaker of the U.S. House of Representatives.

But Hastert’s darkest day in a federal courtroom could still be ahead of him — especially if he fights a jail sentence.

That’s because the plea deal he struck with prosecutors appears to leave open the possibility that embarrassing details of sexual misconduct could spill out at his Feb. 29 sentencing hearing, legal experts said.

RELATED — Mark Brown: Feds need to divulge Hastert’s past misconduct Timeline: Dennis Hastert’s life, career, indictment

Hastert, once second in line to the presidency, appeared resigned to his new reality when he arrived Wednesday at the Dirksen Federal Courthouse. This time, barriers prevented news cameras from mobbing Hastert, 73, as he stepped out of a black SUV on a rainy Chicago morning.

Roughly an hour later, the Plano resident stood before U.S. District Judge Thomas Durkin and seemed to close his eyes, listening as a prosecutor outlined the illegal structuring of bank withdrawals alleged in Hastert’s 15-page plea agreement. That document also notes Hastert lied to the FBI about a $3.5 million hush-money scheme.

Durkin asked Hastert to describe his crime in his own words. Hastert acknowledged in a statement he began withdrawing cash in $9,000 increments to avoid his banks’ questions about earlier withdrawals of as much as $50,000. And he said he knew it was wrong.

“I didn’t want them to know how I intended to spend the money,” Hastert said.

Moments later, Hastert leaned his head toward a microphone and said, “guilty, sir,” as he admitted to a structuring charge that could net him as many as six months in prison. The charge of lying to the FBI will be dropped after his sentencing under the terms of the plea deal.

Hastert withdrew $1.7 million in hush money from bank accounts between 2010 and 2014, handing it over to someone known only as “Individual A.” Hastert had ultimately agreed to pay that person $3.5 million.

He did so to cover up sexual misconduct with a male student dating to his time as a teacher in Yorkville, sources have told the Chicago Sun-Times.

Hastert illegally structured the withdrawal of $952,000 to evade banks’ reporting requirements for transactions of $10,000 or more. When the FBI asked Hastert about it, he lied and said he kept the cash in a safe place, according to the plea deal.

Coincidentally, Hastert pleaded guilty in Chicago the same day House Republicans in Washington D.C. nominated Wisconsin Rep. Paul Ryan to become speaker of the chamber Hastert long ruled.

Now lawyers will prepare for Hastert’s sentencing hearing. His defense attorneys said they don’t intend to call witnesses to testify Feb. 29, but prosecutors didn’t rule it out.

U.S. Attorney Zachary Fardon’s office also released a statement that promised as part of the sentencing to “provide the court with relevant information about the defendant’s background and the charged offenses.”

The alleged misconduct that prompted Hastert’s hush-money scheme is “certainly relevant,” former federal prosecutor Jeffrey Cramer said. Those details could come out if Hastert tries to argue his good works warrant a lenient sentence on the low end of an advisory range of zero to six months in prison.

“The government’s not just going to sit on their hands while listening about all the good things Mr. Hastert has done over his career,” Cramer said.

Andrew Herman, an attorney for the Miller & Chevalier law firm in Washington, D.C., predicted Hastert’s lack of a criminal record would keep him from winding up behind bars, though.

Hugh Mundy, an assistant professor at The John Marshall Law School, said Hastert’s attorneys should express contrition, ask for a six-month sentence and prepare their client to report to prison immediately rather than risk embarrassing public arguments.

Cramer, who now heads the Chicago office of Kroll Inc., said Hastert’s structuring of $952,000, allegedly across 106 withdrawals, “reasonably warrants some jail time.” But he said probation isn’t out of the question.

Neither is the possibility that the public could finally learn the identity of “Individual A.”

“All those things are still on the table,” Cramer said.

Former U.S. House Speaker Dennis Hastert, center, arrives at the Dirksen Federal Courthouse on Wednesday. | Matt Marton/Associated Press

Former U.S. House Speaker Dennis Hastert, center, arrives at the Dirksen Federal Courthouse on Wednesday. | Matt Marton/Associated Press

Dennis Hastert plea agreement

Dennis Hastert indictment

Contributing:Mark Brown

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