Hastert, once second in line to the presidency, is expected to return Wednesday to the Dirksen Federal Courthouse and plead guilty at 8:30 a.m. to criminal wrongdoing in front of U.S. District Judge Thomas Durkin. The hearing comes five months to the day after the May 28 indictment that charged Hastert with skirting banking laws and lying to the FBI.

The 73-year-old from Plano hasn’t shown his face in court since June 9, when he fought through a horde of TV cameras on the way to his arraignment and pleaded not guilty. He looked haggard and barely spoke above a whisper when answering the judge’s questions. On Wednesday, he will be forced to repeat the ordeal.

But this time, Hastert is expected to admit he broke the law. And if he is like most criminal defendants, Hastert is fearing the unknown as that historic moment approaches, veteran Chicago defense attorney Michael Ettinger said.

“It’s bad enough you’ve got to plead guilty and you’re looking at jail,” Ettinger said. “And then you’ve got the press all over you. It’s something I’m sure he wishes he didn’t have to go through.”

It’s still not clear what charge Hastert will admit to, or if he will ultimately face prison time. The two counts against him each carry a maximum sentence of five years behind bars.

Though Hastert will likely be sentenced at a later date, clues to his fate might be found in his plea agreement with prosecutors. That document likely won’t be made public until after the hearing. Typically, those agreements outline any sentencing deals defendants have reached with the feds.

Hastert’s agreement will also be mined for clues that might shed any light on the alleged hush-money scheme at the center of his case, as well as the identity of the person known only as “Individual A.”

The indictment against Hastert alleges he withdrew $1.7 million in hush money from bank accounts between 2010 and 2014, handing it over to “Individual A.” Hastert had ultimately agreed to pay that person $3.5 million, the indictment alleged. He did so to cover up sexual misconduct with a male dating to his time as a teacher in Yorkville, unnamed sources have told the Chicago Sun-Times.

Thomas Green, Hastert’s lawyer, has called that leak of information “unconscionable.”

Between June 2010 and April 2012, the indictment said, Hastert made 15 withdrawals of $50,000 from his bank accounts and gave the cash to “Individual A” every six weeks. But bank employees began to question Hastert about the withdrawals in April 2012. And by federal law, those banks were required to file a currency transaction report for any transaction exceeding $10,000.

So in July 2012, Hastert allegedly began withdrawing the cash in increments of less than $10,000. He still gave the cash to “Individual A” in $50,000 increments, according to the indictment. Roughly two years later, in 2014, Hastert and “Individual A” allegedly changed their arrangement. Hastert began giving that person $100,000 every three months, but he continued to make withdrawals of less than $10,000.

The former speaker illegally structured the withdrawal of $952,000 to evade the banks’ reporting requirements, the feds claim. And when the FBI asked Hastert if he withdrew the money because he didn’t trust the banks, he allegedly lied and said, “Yeah … I kept the cash. That’s what I’m doing.”

The indictment left Hastert’s former associates stunned and puzzled. He immediately resigned as a board member of the CME Group and from the Washington D.C.-based law firm Dickstein Shapiro, where he was a lobbyist. Wheaton College soon renamed the J. Dennis Hastert Center for Economics, Government, and Public Policy, dropping the reference to the former speaker. The Volo Auto Museum even said it would put a 1942 Lincoln Zephyr once owned by Hastert into storage.

Hastert started his political career when he won a 1980 election to the Illinois General Assembly. He was elected to the U.S. House in 1986. He rose in leadership, becoming the chief deputy whip under former Rep. Tom DeLay, R-Texas, in 1994. Ultimately, Hastert locked in the votes to become speaker on Dec. 19, 1998, replacing Newt Gingrich, who decided to quit.

But Hastert’s ascent to become the longest-serving Republican speaker was also marked by a series of scandals befalling others. He assumed the speakership when front-runner Bob Livingston bowed out over an extra-marital affair.

And then, Hastert played a leading role in the impeachment of President Bill Clinton.