Former U.S. House Speaker Dennis Hastert is surrounded by officers as he leaves the federal courthouse last year. (Jim Young/Reuters)

Former U.S. House speaker Dennis Hastert is scheduled to be sentenced Wednesday for violating federal banking laws as he attempted to pay off someone who alleged the Illinois Republican sexually abused him decades ago. The hearing in federal district court in Chicago will mark another low point for Hastert — a once revered high-school teacher and wrestling coach in Illinois who ascended to the highest levels of American politics.

The previous hearings in the case have been relatively tame, mostly void of the shocking allegations that have been leveled against Hastert. Wednesday will be different. Prosecutors revealed in a recent court filing that five people alleged Hastert molested them or at least touched them in inappropriate, questionable ways. One is expected to testify at the hearing, as is the sister of another who has since died.

Here are the four critical questions we’ll be looking to answer as we watch the proceedings. The hearing begins at 10 a.m. central time.

1) Will Hastert get prison time, and if so, how much?

The longest-serving Republican House speaker, Dennis Hastert, has pleaded guilty to lying to the FBI and violating federal banking laws to cover up payments he allegedly made to hide past sexual "misconduct." (Monica Akhtar,Gillian Brockell/The Washington Post)

This is, of course, the question at any sentencing, but predicting a sentence in Hastert’s case is particularly tricky. At Hastert’s plea, prosecutors and defense attorneys agreed that federal sentencing guidelines in the case call for a prison term between zero and six months. Prosecutors said they would recommend a term in that range, and in pre-sentence filings, they did exactly that — not suggesting a more specific figure. Hastert’s defense attorneys argued a sentence of probation would be appropriate.

But U.S. District Judge Thomas Durkin is not bound by any of those recommendations. He could sentence Hastert to as many as five years behind bars. And in other hearings, Durkin has not proved himself to be especially sympathetic to Hastert’s point of view on narrowing what should be fair game to consider.

Durkin agreed, over the objection of defense attorneys, to let a purported victim testify at the sentencing, saying such testimony “informs my decision about the history and characteristics of the defendant.” He also said he would take into consideration that Hastert initially told FBI agents one of the alleged victims of sexual abuse was extorting him — a claim investigators later found to be false.

“That’s not conduct that’s 40 years old. That’s conduct that’s less than a year old,” Durkin said, according to the Chicago Tribune. “Among the aggravating factors in this case, that’s a big one.”

2) What will the victims (or their representatives) say?

Prosecutors have said they expect at least one man who alleged he was abused by Hastert decades ago to testify at the sentencing, and they also expect testimony from Jolene Burdge, a woman who has claimed publicly her brother was abused by Hastert. Burdge has already told her story to ABC News, but Wednesday would mark the first time that a man known as “Individual D” has publicly shared his experience with Hastert.

His testimony would surely be emotional. In sentencing papers, prosecutors wrote that Hastert abused Individual D when he was just 17 years old and a member of the Yorkville High School wrestling team. By their account, the teen asked Hastert for help cutting weight, and Hastert told him “that a massage could take some pounds off.”

Hastert had the teen to lie down on a table, then took off the teen’s pants and performed a sex act on him, prosecutors wrote. The Chicago Tribune, citing an anonymous source, reported that Hastert called Individual D’s relatives, hoping they would write a letter asking for leniency at sentencing, and Individual D then called federal prosecutors offering a statement about what Hastert did to him.

3) How will Hastert look?

According to Hastert’s defense attorneys, Hastert is in poor health. The 74-year-old, they have written, needs help getting out of bed, using the bathroom and dressing himself. He can walk short distances with a walker and an assistant, though he is mostly wheelchair bound, they have asserted. They have asked that his medical condition be considered as a part of his sentencing.

At Hastert’s plea in October, he seemed to be moving around fine — albeit with his iconic hunch. Defense attorneys wrote that his health deteriorated rapidly after that. It will be interesting to see how he looks Wednesday.

4) What, if anything, will Hastert say?

In court filings, Hastert’s defense attorneys have asserted that Hastert is thoroughly sorry and ashamed. They have, in general terms, acknowledged the sexual misconduct of which Hastert is accused.

Thomas Green, Hastert’s attorney, said in a recent statement: “Mr. Hastert acknowledges that as a young man he committed transgressions for which he is profoundly sorry. He earnestly apologizes to his former students, family, friends, previous constituents and all others affected by the harm his actions have caused.”

But Hastert himself hasn’t truly addressed the darkness at the center of his case — either to reporters or in court. At his plea, he addressed the financial charge of which he was convicted but did not comment on the underlying, sexual allegations.

“I didn’t want them to know how I intended to spend the money,” Hastert said then, when asked to describe his misdeeds.

Hastert will be offered the opportunity to speak on Wednesday, and demonstrating remorse could help him win a lighter sentence. We’ll be watching closely to see what he says.