The sentence hearings are scheduled to begin at 8:30 a.m. Wednesday morning in Washington, D.C. Jackson Jr. and his wife Sandi have already plead guilty, which helps in sentencing.
From rising star to fallen felon -- Jackson Jr. is facing up to four years in federal prison. Tuesday night, his family is gathering at his father's D.C. home.
A Jackson family friend who arrived at the home Tuesday evening asked for privacy and respect, saying this is a personal matter.
"It's not a proud day. I'm sorry I let everybody down," said Jesse Jackson, Jr., while leaving a court in February.
On the eve of the court hearing that could end with a four-year prison sentence, Jesse Jackson, Jr. asked the judge to seal details about his bipolar disorder.
The illness figures prominently in his pleas for leniency. But the Bureau of Prisons responded that its doctors are more than capable of treating him.
Sandi Jackson, who is facing a maximum of 18 months, also made a request. She's asking for probation and promises to perform community service at a Washington D.C. food pantry visited by presidents.
On Wednesday morning, both Jacksons are expected to make their pleas directly to the judge.
"I think one of the things that's going concern the judge is how much genuine remorse is there?" said Prof. Richard Kling, IIT Chicago-Kent College of Law.
How did a once-shooting political star fall so far?
In court filings, prosecutors point out Jackson looted his campaign fund for seven years to the tune of $750,000.
Prosecutors wrote: "Getting embroiled in the Blagojevich scandal did not make [Jackson] stop stealing. Instead, his reaction was to devise new ways of stealing."
Stanley Brand is Washington criminal defense attorney who once represented Dan Rostenkowski. He says for some, sentencing day is actually a relief.
"The pressure that comes from being under federal investigation for this length of time over serious matters certainly has to take its toll," said Brand.
One interesting footnote: the judge once represented a former congressman who was convicted of bribery. In that case, she argued that he deserved leniency because of all of his years of public service. The Jacksons are expected to make a similar argument Wednesday morning.