Things keep getting worse for Dennis Hastert.

First, the former U.S. House speaker’s odds of staying out of prison seemed to dim Wednesday when the federal judge presiding over his case asked pointed questions about Hastert’s alleged attempt to falsely make himself out to be a victim of extortion in 2015.

Then, it became clear Hastert has another problem: The so-called Individual A, allegedly molested as a teenager by Hastert, has insisted Hastert make good on their $3.5 million hush-money deal in 2010, according to a document unsealed by order of U.S. District Judge Thomas M. Durkin. Individual A collected just $1.7 million from Hastert.

“Individual A may still go public if he pursues Mr. Hastert civilly, as his lawyer has threatened to do if Mr. Hastert does not pay Individual A the remaining $1.8 million from their initial arrangement, plus statutory interest,” Thomas Green, Hastert’s attorney, wrote.

Kristi Browne, an attorney representing Individual A, declined to comment.

Hastert pleaded guilty to a financial crime last year and faces sentencing April 27. But federal prosecutors used a damning 26-page sentencing memo last week to accuse Hastert of sexually abusing five students while a wrestling coach at Yorkville High School decades ago.

It also alleges Hastert claimed in February 2015 that he was the victim of an extortion plot by Individual A, whose identity has not been publicly revealed. Hastert entered into a proffer agreement and secretly recorded two phone conversations between himself and Individual A for the feds in March 2015.

In comments Durkin described as a “preview” of the sentencing hearing, the judge made clear he wants to consider the lies Hastert told in that proffer.

“That’s not conduct that’s 40 years old,” Durkin said. “That’s conduct that’s less than a year old.”

Prosecutors said Jolene Burdge, who claims her brother was a victim of Hastert’s abuse in the 1970s, will testify. So will the person known as Individual D, who prosecutors say was molested by Hastert and recalled the La-Z-Boy-style chair Hastert placed in direct view of the boys’ locker room shower stalls in Yorkville High School.

The feds told the judge they didn’t expect a need for restrictions to protect confidentiality at the hearing. And the judge said both witnesses would be placed under oath and subject to questioning — “it’s only fair.”

Meanwhile, the judge also ordered a document unsealed that challenges the conclusion reached by probation officials that Hastert’s sentence should be enhanced for obstructing justice. Probation officials also concluded Hastert hasn’t accepted responsibility for what he’s done and doesn’t deserve a break at sentencing for it.

The unsealed document reveals a probation officer found “troubling” a suggestion by Hastert’s lawyers that the alleged conduct with Individual A might not qualify as sexual misconduct.

“While undoubtedly many would consider this episode as described by [Individual A], consisting of a groin rub for a groin pull and a massage, to be misconduct, we are not so certain that the incident qualifies as sexual misconduct, especially for a coach and trainer 42 years ago,” Hastert’s lawyers are quoted as writing.

His lawyers also labeled as “unnecessary” a recommendation that Hastert undergo a sex offender assessment and submit to a polygraph to reveal “any recent misconduct.”

Despite the developments, former federal prosecutor Jeffrey Cramer said it wouldn’t be unreasonable for the judge to give Hastert probation. But Cramer pointed out that Hastert’s life is now bookended by allegations of criminal conduct — by claims of sexual misconduct in the 1970s and of leading FBI agents on a wild goose chase in 2015.

Cramer stressed, “there are no winners here,” but he said Hastert could face a few months in prison.

Patrick Collins, another former federal prosecutor and now partner at Perkins Coie, said Durkin is unlikely to make up his mind about Hastert’s punishment until all the evidence has been heard at sentencing — and that includes any comments from Hastert himself.

Collins called that “perhaps the most important moment in any criminal sentencing.”

“And in many cases, that can be a game changer for the court,” Collins said.

Hastert Response