J. Dennis Hastert had risen to the highest levels of American politics without any of the sordid allegations about his past coming to light. So when the FBI started asking questions about his unusual cash withdrawals, he tried a dangerous gambit: He told the agents he was an extortion victim, and he agreed to surreptitiously record his calls to help them catch the culprit.

Investigators soon concluded that the former U.S. House speaker — an Illinois Republican who had won the trust of countless students he had taught and wrestlers he had coached before he entered politics — was lying. By their assessment, Hastert had, decades earlier, sexually abused the man he claimed was extorting him, then paid him $1.7 million to keep quiet.

Since then, authorities have uncovered four other possible victims, all of whom were teenagers affiliated with the wrestling team at the high school where Hastert coached. They say he abused them or made questionable, inappropriate contact. Hastert pleaded guilty in October to a bank-related charge that made no mention of the alleged sexual misconduct. But when a judge sentences the 74-year-old Wednesday, he will consider prosecutors’ assertion that the once-revered coach, teacher and politician was a serial child molester.

In Yorkville, the small town outside of Chicago where Hastert coached and taught, and in the corridors of the Capitol where he once wrangled fellow Republican legislators, the revelations about the purported sexual misdeeds have been met with shock, outrage and a significant amount of soul searching.

In this 1975 photo, then-high school wrestling coach J. Dennis Hastert, left, and Illinois State University wrestling coach Larry Meyer watch a wrestling move. (The Pantagraph/Associated Press)

Former wrestlers and students have called one another, trading theories about who the victims might be and asking about signs they might have missed. Former staffers have racked their brains trying to re-create some of the high-profile incidents Hastert weathered while in office, wondering whether the skeletons in his closet might have secretly informed his decision-making.

“In the back of his head, he must have been thinking, ‘Oh my gosh, they’re going to find me out,’ ” said one former Hastert staffer.

Thomas Green, Hastert’s attorney, said in a statement responding to the allegations: “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.”

Hastert’s rise to prominence was remarkable — especially in light of what he is accused of now. He began his career as a history teacher and coach at Illinois’s Yorkville High School, where he enjoyed a “pretty sterling” reputation, said Fred Kindelberger, 67, of Milwaukee, who wrestled on one of Hastert’s teams. Hastert also led a Scout group, taking boys on scuba-
diving trips to the Bahamas and canoeing expeditions in the Boundary Waters area of Minnesota.

Hastert wrote fondly of those times in a memoir published in 2004, describing how he tried to impart values and life lessons to those in his care.

“I was never a very good liar,” he wrote, detailing an incident in which he tried unsuccessfully to deceive his mother. “Maybe I wasn’t smart enough. I could never get away with it, so I made up my mind as a kid to tell the truth and pay the consequences.”

To a man, former pupils, athletes and Scouts contacted by The Washington Post said they saw no signs Hastert was abusing anyone.

“Nothing at all makes sense to me,” said Bill Loftus, 64, a former wrestler who still lives in Yorkville. “To me, Denny was the greatest guy. If it wasn’t for him, I might not have even graduated. He just showed me great respect, and it made me want to do good.”

That is not to say all those who knew Hastert doubt the allegations against him. Jim Stott, 64, a draftsman and former wrestler who lives in Yorkville, said that when Hastert was first charged in 2015, he was skeptical. But when prosecutors provided details of their investigation in a recent court filing, Stott began to think “maybe it did happen.”

David McNelis, 63, a former wrestler who lives in Plano, Ill., said, “It’s like he molested all of Kendall County now.”

Republican Party leaders appointed Hastert to his first office in politics — a seat in the Illinois House of Representatives — in the early 1980s to replace a member who was terminally ill. His mentor, a state senator named John E. Grotberg, would go on to win a seat in the U.S. House of Representatives, and when Grotberg, too, fell ill, Hastert ran to fill the vacancy. (Grotberg died in 1986).

In Congress, Hastert played a pivotal role in health-care and drug policy issues. His ascension to the speakership, though, was almost by accident. When Rep. Newt Gingrich (R-Ga.) resigned from the post after the 1998 midterm elections — in which Republicans lost five seats despite President Bill Clinton’s affair with Monica Lewinsky — Rep. Bob Livingston (R-La.) was tapped to succeed him. Then Livingston was forced to acknowledge that he had had an affair. Hastert took the speakership instead, putting him second in line to succeed the president.

Hastert led the House until 2007 — making him the longest-serving Republican House speaker in history. The end of his time, though, was marked by scandal, as Rep. Mark Foley (R-Fla.) resigned amid reports that he had sent sexually explicit messages to an underage male Capitol Hill page.

Former Hastert staffers and other congressional aides said they never saw Hastert interact inappropriately with pages, and the U.S. Probation Office found “no evidence of any sexual misconduct since approximately 1979,” court documents show.

But those who worked closely with Hastert or for him wonder whether his handling of the Foley scandal was affected by his past. One former House staffer said Foley’s interest in pages was a poorly kept secret, even before the explicit messages were uncovered, and the former staffer never understood why Hastert or those working for him did not do anything about it sooner. “I thought it was more than weird,” the former House staffer said.

The former Hastert staffer said they questioned why, after the explicit messages emerged, it took so long for the speaker to take ownership publicly.

“Knowing what we know now, he must have been thinking to himself, ‘They’re going to find me out, at some level here, something will come out of all of this,’ ” the former Hastert staffer said.

A different former aide said Hastert moved swiftly to oust Foley once his misdeeds became public and that Hastert was ­never suspected of similar wrongdoing.

“There’s no indication that there was anything like that going on in the last 40 years,” he said.

All the former staffers spoke on the condition of anonymity so as not to affect their current employment.

Even prosecutors remarked in sentencing papers on how Hastert achieved such a high-profile position with the alleged misdeeds in his past.

“Defendant was so sure his secrets were safe that he apparently had no fears about entering a profession where one is subject to constant scrutiny and media attention,” they wrote.

They ultimately charged Has­tert with structuring — withdrawing money in amounts low enough that they wouldn’t trigger federal reporting requirements — because the federal and state statutes of limitations had “long expired on potential charges relating to defendant’s known sexual acts,” they wrote in court papers. They wrote that when investigators were initially tipped to Hastert’s suspicious cash withdrawals, they did not know what to think and wondered whether Hastert was a victim of extortion. Hastert claimed as much after agents approached him, saying a person identified in court papers as Individual A was making false claims about sexual abuse.

The agents’ thinking changed after Hastert agreed to record phone calls with Individual A. They quickly realized the man’s “tone and comments during the recorded conversation were inconsistent with someone committing extortion.” And when they pressed Hastert to confront the man about his purportedly false allegations, Hastert ignored their instructions.

Investigators would come to learn that Individual A, who met Hastert as a child through family, was a former wrestler who alleged Hastert touched him in an inappropriate, sexual way on a team trip decades ago. The man confronted Hastert around 2010 and agreed to keep quiet if Has­tert, who became a lobbyist after leaving the House, paid him millions of dollars. Investigators soon found four other possible victims. Two former wrestlers alleged Hastert performed sexual acts on them after offering a massage. A third said Hastert brushed his genitals, though he was not sure whether the contact was on purpose.

The fourth, Steven Reinboldt, is deceased. His sister has said publicly that her brother confided in her that his first gay sexual experience was with Hastert. A former wrestler, who spoke on the condition of anonymity to protect his privacy, confirmed to The Washington Post that Reinboldt shared a similar story with him years ago, though at the time, Reinboldt was out of high school and the former wrestler was not sure exactly when the contact occurred.

“While defendant achieved great success, reaping all the benefits that went with it, these boys struggled, and all are still struggling now with what defendant did to them,” prosecutors wrote in a court filing. “Some have managed better than ­others, but all of them carry the scars defendant inflicted upon them.”

Some former wrestlers said the town where Hastert was once beloved is now wary of him. His alma mater, Wheaton College, took his name off a public policy center he helped create.

Prosecutors have asked that Hastert face a sentence of up to six months in prison and that he be required to undergo a sex offender assessment. Reinboldt’s sister and at least one alleged victim are expected to testify at his sentencing.

Hastert’s attorneys have said he is in such bad health that he needs help getting out of bed, using the bathroom and dressing himself. They want him to face only probation.

“By any measure, appearing before this Court to receive its sentence will be the most difficult day in Mr. Hastert’s life,” defense attorneys wrote in a court filing. “Mr. Hastert’s fall from grace has been swift and devastating.”