At one point, Jackson led the assembled inmates in a chant: "Even though... I'm in jail... jail... is not in me."
The event, a Christmas Day tradition for Jackson's Rainbow PUSH coalition, was held for inmates at the Cook County Boot Camp. The program for non-violent offenders aims to rehabilitate men and women through military-style discipline, education, and training programs.
"The place for dignity is in jobs," said Jackson. "That means investing. These young men and these young women need a trade skill."
Along with the message of personal responsibility and calls for more job creation, this year's 38th annual event combined a rousing service, a serious message, and a sprinkling of mayoral politics.
Former mayoral candidate and current State Senator Rev. James Meeks talked publicly Saturday for the first time since dropping out of the race.
"The things that will get you locked up you've got to stay away from," said Meeks.
On Christmas Day, Meeks repeated his call for only one African American to run for mayor.
"We can only win with a strong black candidate," said Meeks. "I want all of them to get together and choose one person."
Jackson seemed to echo, at the very least, Meeks's political analysis of the chances for the African-American candidates in the race.
"It's going to be difficult to get one camp through the eye of a needle," said Jackson. "Two cannot get through the eye of a needle. It's a big decision they have to make."
Former U.S. senator Carol Moseley Braun and Congressman Danny Davis, two African-Americans running for Chicago mayor, both say they intend to stay in the race. Appearing at Jackson's event, Davis said the prospect of a runoff election could narrow the field anyway.
"I think the people will determine a consensus candidate," said Davis. "Once they get an opportunity to actually vote, they will determine who the consensus candidate is."
Congressman Jesse Jackson, Jr. was also present at the event. It was a rare public appearance following questions about his dealings with former governor Rod Blagojevich and revelations of an extra-marital affair.
"I'm not here to blame you for no error in judgment," Jackson, Jr., told the inmates. "Everybody's fallen short of the glory of God."
Meanwhile, sources tell ABC7 that former president Bill Clinton is planning to campaign for Rahm Emanuel, who served as a senior advisor in Clinton's administration. A joint appearance could happen sometime during January.
Recent polls show Emanuel leading the field of candidates, but many voters remain undecided.