Jesse Jackson Jr.’s past and future in the spotlight as he jumps back into political life

As former Congressman Jesse Jackson Jr. stages a comeback that will upend the open race for the 2nd Congressional District, his competitors are prepared to pounce on his past.

Jackson Jr., 60, plans to announce his run for the seat this week, according to his spokesman. Jackson Jr. in July formed an exploratory committee, angling for a return to the seat he held for 17 years. He has since been touring the district, registering voters and raising money, including at a Congressional Black Caucus fundraiser on Sept. 26 in Washington D.C.

Voters in the district that now stretches south and west will have to weigh whether they want to continue a political family dynasty — and give another chance to a man who comes with some historical baggage. Jackson Jr. left Congress in 2012, amid a battle with bipolar depression and ultimately, federal charges centered on misusing his campaign funds.

Declared candidates in the race include State Sen. Robert Peters, Cook County Commissioner Donna Miller, State Sen. Willie Preston, Metropolitan Water Reclamation District Commissioner Yumeka Brown, businessman Eric France, policy strategist Adal Regis and youth pastor and advocate Jeremy Young.

At least one of the candidates says he welcomes Jackson Jr. to the race — and will press him on accountability of his past.

“I want him to run. I love it because it gives us an opportunity to be able to have real discussions about where Black Americans see themselves, and the type of leadership that we are craving, this year at this point in our history, in this country,” Preston said. “So I welcome him into the race. He’s frolicking with D.C. consultants. He is hosting fundraisers. He’s asking everyone to give him money. Something he’s familiar with doing, but he hasn’t announced. He hasn’t even set up a PAC, but he’s hosting fundraisers. So it’s going to be interesting to see if he’s drawing outside the rules again, like he did when he left.”

Preston, who has pushed Gov. JB Pritzker for a state commutation for Gangster Disciples co-founder Larry Hoover, said he believes in “redemption,” but said he doesn’t believe Jackson Jr. has fully acknowledged his actions.

“I believe in redemption. I come from a place where I felt for this state to be a state that recognizes that people do, and can, change. But I can tell you, when someone isn’t fully acknowledging the wrongs that they did, that’s not redemption,” Preston said.

Jackson Jr. ‘took responsibility for his actions.’

In a December WTTW interview, Jackson Jr. repeated the claim that he asserted during his court proceedings in 2013: “I lived in my campaign fund, and I owned my behavior for that.” Jackson Jr. also fought back the characterization that he “took” $750,000 from his campaign.

Prosecutors repeatedly used the words “stole” and “stolen” during Jackson’s sentencing hearing on Aug. 14, 2013.

“The defendant stands before the Court for sentencing having admitted to orchestrating a conspiracy to steal $750,000 from a federal campaign. Both the dollar amount stolen and the length of the conspiracy, which lasted about seven years, are staggering,” Assistant U.S. Attorney Michael A. Graves said.

U.S. District Court Judge Amy Berman Jackson called it a “knowing, organized, joint misconduct that was repeated and then covered up over a period of years.”

“The public is already sadly cynical about the integrity of its public officials and the role that money plays in the electoral process, and your conduct stained not only your reputation but the way in which all elected officials are viewed,” the judge said during sentencing.

 Former U.S. Rep. Jesse Jackson Jr., D-Ill., and his wife, Sandra, arrive at federal court in Washington in 2015.

Former U.S. Rep. Jesse Jackson Jr., D-Ill., and his wife, Sandra, arrive at federal court in Washington in 2015.

Susan Walsh/AP

Jackson Jr. pleaded guilty to charges of conspiracy to commit wire fraud, mail fraud and false statements. His then-wife, former Ald. Sandi Jackson, pleaded guilty to filing a false federal income tax return.

According to the U.S. Attorney’s Office, Jackson Jr. conspired to defraud his re-election campaigns of about $750,000 in funds that were used to pay for a range of personal items and expenses, including furs and cashmere capes, a $43,000 Rolex watch, Michael Jackson memorabilia and mounted elk heads.

Jackson Jr. also admitted taking steps to conceal seven years of illegal activities, including the filing of false and misleading reports with the Federal Election Commission and the U.S. House of Representatives.

During sentencing, Jackson acknowledged, “I didn’t separate my personal life from my political activities, and I couldn’t have been more wrong.

“I take responsibility for my actions. I’m very sorry for what I’ve done, what I did. My whole life was political. Everything I did was political. Everything that I considered to be part of the campaign, I just lived that way,” Jackson Jr. said.

Jackson Jr. spokesperson John Digles defended Jackson Jr’s admissions, telling the Sun-Times that he “took responsibility for his actions.”

“He did exactly what the judge required of him. He took his time. I mean this has been a decade that he’s taken his time to work, to be a better man and to grow and go through a process of forgiveness, prayer and reflection,” Digles said. “And he arrives at this place. He also took the last five months to talk to voters across the district eye to eye. He’s not hiding anywhere. He has taken responsibility. He owns his journey and his life experience will matter.”

The Jackson family dynamic

Preston posed with U.S. Rep. Jonathan Jackson during the Sept. 26 CBC fundraiser. So did Jackson Jr. Jonathan Jackson was also listed as a special guest on the D.C. fundraiser invite.

Asked whether the CBC plans to endorse a candidate in the race, a spokesman said, “This is not a race that we’re engaging in.”

U.S. Rep. Jonathan Jackson speaks to reporters after trying to tour an Immigration and Customs Enforcement (ICE) facility, the Intensive Supervision Appearance Program (ISAP) office at 2245 S. Michigan Ave. in the South Loop, Tuesday, June 17, 2025.

U.S. Rep. Jonathan Jackson speaks to reporters after trying to tour an Immigration and Customs Enforcement (ICE) facility, the Intensive Supervision Appearance Program office at 2245 S. Michigan Ave. in the South Loop June 17.

Ashlee Rezin/Sun-Times

Jonathan Jackson’s office had no comment when asked whether he supported his brother’s pending campaign. But the congressman gave his brother glowing reviews at the fundraiser.

“Let me give you perspective from a brother of Jesse Jr., my congressman. I want to say thank you for your years of service and I look forward to you returning back to the Capitol,” Jonathan Jackson said, according to videos posted on social media.

Jonathan Jackson said he couldn’t think of “someone that’s more prepared, that understands the Constitution and the country, that could service the nation better and if I did know of someone, I’ll be glad to support them. It just so happens that my brother’s the most qualified to do something.”

Preston said he will not ask Jonathan Jackson to support his campaign, saying he wouldn’t try to “come between family members.” But he offered that Illinois doesn’t want another political dynasty.

Inmates greet Rev. Jesse Jackson during Christmas Day services held by Rainbow PUSH at Division 11 of the Cook County Jail, 3015 S. California Blvd., on Wednesday, Dec. 25, 2024.

Inmates greet Rev. Jesse Jackson during Christmas Day services held by Rainbow PUSH at Division 11 of the Cook County Jail Dec. 25, 2024.

Zubaer Khan/Sun-Times

“Congressional offices are not family heirlooms, and that is what some folks are trying to push forth on us,” Preston said. “But you know, we’re done with dynasties in this country. I can tell you there are serious questions being raised as to if we’re going to have one brother in a congressional district, and the next brother in the 2nd Congressional district. I don’t think that folks want that. We don’t want that.”

The power of name recognition

Other candidates in the race acknowledged the Jackson family name recognition will factor into the race.

“We saw that when Jonathan Jackson ran, and it will be significant again. But I don’t think it’s insurmountable,” said Delmarie Cobb, a consultant for Miller’s campaign and Jackson Jr.’s former campaign. “…One of the things I have learned over the course of doing campaigns that is that every five years, you have a new crop of voters, and those voters don’t necessarily know who you are, if you’ve been in office a long time, or if you’ve been out of office for a long time and decide to make a comeback.”

U.S. Rep. Robin Kelly, who in May launched her bid for Sen. Dick Durbin’s Senate seat, told the Sun-Times she is not also collecting signatures for her 2nd Congressional seat.

“When I decided I was going to run, I was going to run. And I wasn’t going to do the two, but people put it out there so people wouldn’t think I was 100% in. But I’m 100% in. I’m not running for my old seat,” Kelly said.

Kelly said she has spoken to “the majority” of people who are running for her seat. But that doesn’t include Jackson Jr.

“Nope, he hasn’t [reached out],” Kelly said.

Trump pardon?

Jackson Jr. was denied a pardon by President Joe Biden on Jan. 20, in his final hours in office. Jackson Jr. spent 17 of his 30 months in federal prison before being released in 2015 to a halfway house in Washington, D.C.

“It would change the course of my life,” Jackson Jr. said of a potential pardon in December. “It would be the official act by the president of the United States on behalf of the American people to say that ‘you are forgiven.'”

But Jackson Jr. has no plans to ask Trump for a pardon, according to his spokesman.

“He has no intention to do that,” Digles said. “His whole focus as he’s done this, is he’s gone around the district talking to people who have been through a very similar journey that he’s been through, and he’s thinking a lot more about parts of that than he is for himself.”

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