"I think the likelihood [of Madoff returning home] is very slim. I'm sure his attorney told him to pack his toothbrush after his guilty plea," said CBS' The Early Show legal analyst Lisa Bloom. "For his attorney to show why he should continue to have his freedom, I don't expect to see that."
Bloom added that with, Madoff potentially faces 150 years in prison, making him an increased flight risk.
But CBS News chief legal analyst Andrew Cohen doesn't think it's a foregone conclusion the judge will see Madoff as a risk to run.
"As soon as the judge accepts Madoff's plea the defendant loses his presumption of innocence and that makes his bail argument that much harder to make," said Cohen. "But he's no more a flight risk than he was before and in fact the judge may give him some credit for taking some responsibility. I don't think it's a guarantee that he goes to prison right away."
Should Madoff's request to stay in his penthouse be rejected, where could he end up?
Bloom explains that Madoff will likely be first sent to a city correctional facility until he is sentenced. And if he receives a term longer than 25 years, "No Club Fed," Bloom quipped, referring to the nickname for minimum-security prisons where many white collar criminals serve their sentences.
And would a guilty plea from Madoff close the book on the fraud investigation?
"Just because Madoff apparently won't cooperate with authorities doesn't mean we won't perhaps see charges against other people here," said Cohen. "There clearly is a paper trail, and clearly people were handling the details of the phony trades, and the investigation is ongoing. When there is this much money at stake the trail won't grow cold here or now."
Cohen said he expects the people that handled the trades, which may have been fabricated, may have to explain why they didn't figure out it was a Ponzi scheme.