The last dinner meal was served at 4:30 p.m., as it is everyday. It was the first meal for Hastert as a federal prisoner. According to the menu, he sat down to eat a meal of bean soup and a deli sandwich.
He was seen rolling himself into the facility in a wheelchair with a woman's help two hours before his 2 p.m. deadline.
The Illinois Republican who presided over the House of Representatives for eight years pleaded guilty to charges he violated banking laws for hush-money paid to someone he sexually molested.
Hastert was sentenced in April in a hush-money case that covered up accusations he sexually abused teenagers while coaching high school wrestling in Yorkville, Illinois.
The Hastert family parked in the regular parking lot on Wednesday and Hastert went in the main entrance, dressed in camouflage pants and a dark shirt, surprising prison buffs who speculated that the former Speaker of the House would invoke whatever clout he had left and use a back shipping entrance as had some lesser politicians over the years.
Instead, the 74-year-old Hastert appeared to struggle up the front ramp using a wheelchair that became necessary after a stroke and other illnesses.
While the sight might have evoked sympathy for a man who was once two heartbeats from the presidency, it is tempered by what Hastert did to get there, sexually abusing boys on the wrestling teams he coached 40 years ago, which prompted Judge Thomas Durkin to label him a serial child molester.
So on Wednesday it came down to just Hastert and a woman who appeared to be his wife, Jean, who dropped him off and quickly left.
Last spring Jean Hastert was more involved, writing this letter to the sentencing judge, begging for mercy because of her husband's public service.
"Denny's selflessness has not been without cost," she wrote. "Because he spent so much of his career away from home helping others, we always looked forward to his retirement so that we could spend more time together."
Their plan was interrupted Wednesday after she left alone in the family's SUV.
And just like that, Hastert went from the 51st speaker of the house to an eight-digit federal inmate.
"On the plus side it says no one is above the law not even the third most powerful political figure in the United States," Gil Soffer, ABC7 legal analyst and former assistant U.S. attorney, said. "The downside is obvious, that the 3rd most powerful politician in he united states committed a criminal act, sufficiently serious that even at the age of 74 and decades after the underlying conduct, he's sitting in jail for a year and a half."
Hastert is facing a civil suit by one of the victims who wants the rest of the $3.5 million in hush money he says they agreed to.
"The suit will stand or fall on its own merits, it doesn't matter if he is in prison or not," Soffer said. "As a practical matter, are they likely to see any money come out of this process? It seems like an uphill battle. I would also make some arguments if I were on the defense side of this saying your trying to enforce something that is essentially unlawful, the payment of hush money. That's not a contract that should ever be enforceable in the first place."
Former federal prison inmate Michael Alcott described the intake process to the ABC7 I-Team.
"When you first arrive you're scared to death and pretty much nobody approaches you. The inmates, they all stay away from you because they need to learn who you are and what you are," Alcott said.
Alcott did six years in federal prison for bank fraud. He tells the I-Team that 74-year-old Hastert is lucky he'll be doing his time in a federal prison hospital.
"Inmates call it the Holiday Inn of the system. It's better food, it's nicer employees, it's better accommodations," Alcott says.
But unlike the Crowne Plaza, there is razor wire on the perimeter and the former Speaker of the House won't be able to leave for dinner at Morton's and come back before bed check.
Ex-con Jason Chez learned that the hard way, doing three years for fraud. He now runs a company in Chicago that targets white collar crime.
"The first day is the worst, it's the scariest because you don't know what to expect," Chez says.
"They're going to issue him his clothes, they'll assign him a bunk, give him an orientation sheet and get him all situated. And it's really the nerves that are the worst and then it becomes very boring after that. And you don't know if people are going to be mean, where you're going to sleep, what you can and can't do," he says.
Hastert is assigned to this medical facility because he has several serious ailments, including having suffered a stroke during the time he was facing federal charges.
"He's in a medical facility mainly and he's in the low section of it, which is like a camp but with a fence and with controlled movements. And they're not violent people there; if you're looking for trouble you can find it but for the most part you're pretty safe," Chez says.
Despite his condition, Chez says Hastert will have some of kind of assigned chore and will have to abide by the federal prison schedule: Up at 6 a.m. for breakfast, lunch at 10:30 a.m., a prisoner bunk count every day at 4 p.m. and dinner at 4:30 p.m. Hastert may also find it hard to hide.
"With his case, everyone knows about it so it's going to be pretty hard to hide it or lie to them and tell them that you're in there for income tax evasion. So, yeah, they're not going to talk to him and they're probably going to yell at him and call him names," Chez says.
Hastert is not expected to do the full 15 months sentence. Under deferral guidelines, he will probably do about 80 percent, which means he will be behind prison walls for a little more than a year.
Some federal prison inmates have been known to use to their failing health as a ticket to an early release. However, ABC7's legal analyst doesn't think Hastert would qualify. The reason he's at this prison facility is because it's a medical facility where they can treat everything that is wrong with him.