Chicago has a busy 2026 ahead. Three Democratic members of Congress are retiring from their seats across the city, which has prompted dozens of candidates to hop into the races in hopes of gaining a long-term incumbency.
There’s Illinois’s Ninth District, where a field of 16 candidates is led by Evanston Mayor Daniel Biss and new-media journalist Kat Abughazaleh. In the Seventh District, 13 candidates are vying for the seat.
But perhaps the most classically “Chicago” race is in Illinois’s Second District, which starts on the South Side of the city and stretches into such south suburbs as Dolton and Blue Island. That race, an open seat because Rep. Robin Kelly is seeking election to the U.S. Senate, raises this question: What could be more “Chicago politics” than a corrupt politician with name recognition trying to rebrand himself and return to Congress?
That’s the story of Jesse Jackson Jr., former congressman and son of civil rights leader Jesse Jackson. Jackson Jr. threw his hat into the IL-02 race 13 years after he resigned from the very same role and was shortly thereafter convicted of stealing $750,000 of campaign funds for personal expenses, including a Rolex, taxidermied elk heads, a $4,600 fedora worn by Michael Jackson, and much more.
Jackson is framing his entry into the race as an almost spiritual redemption project. “Even when I was exiting prison after I was sentenced, I said I still seek forgiveness, and I still seek the restoration and the resurrection of my life and the life of others, and I’m still right there,” he said on WTTW’s Chicago Tonight: Black Voices in 2024.
But his Facebook posts since he was convicted reveal a man who consistently downplays and justifies his crimes, showing a lack of remorse and reflection.
In 2018, Jackson weighed in on Rep. Alexandria Ocasio-Cortez’s (D-NY) struggles to afford an apartment in D.C., writing on Facebook: “This is what happens. Then when you have kids and they need to attend decent schools in DC and you want to have a life while serving, guess what? You start calling everything you do a campaign expense.”
Jackson went on to justify his spending of campaign contributions: “A life long vow of poverty, I did not take for me or my family. [W]hen you truly represent people you have a lot of personal standards that you have to maintain and they are expensive.”
But what Jackson calls not taking a “vow of poverty” was spending three-quarters of a million dollars of campaign money on luxury items and experiences. Jackson spent $43,350 on a gold-plated Rolex. $17,163 at tobacco shops. Nearly $27,000 on various pieces of Michael Jackson memorabilia. $5,800 worth of clothing from a fur shop, including a reversible mink parka and multiple cashmere capes.
“I would buy my kids what they wanted for Christmas, and I said to myself, ‘self, they deserve it, my supporters won’t mind, because I’m working hard as hell,’” he finished the post.
Now, he’s hoping his supporters in the Second District “won’t mind,” or at least won’t remember how his 17 years in Congress ended.
“Jesse Jackson Jr. was considered one of the hardest-working and most effective members of Congress. He never missed a vote,” his campaign website reads. But publicly available data shows a completely different picture—Jackson missed 376 votes over the course of his 17 years in Congress, including a whopping 278 in 2012 alone.
When asked about the discrepancy, John Digles, who heads communications for the Jackson campaign, initially seemed confused: “That’s not our understanding at all. I’m a little confused by that.” He later clarified that the vast majority of Jackson’s missed votes happened after he “ran into his health issues” during his last term in Congress. Between 1995 and 2009, Jackson only missed two votes. In the last six months of 2012, he missed 100 percent of votes held.
Also in 2012, Jackson disappeared from the public eye entirely. His office initially declined to share information about where the sitting congressman was; the Mayo Clinic eventually revealed in a statement that Jackson was being treated there for depression and bipolar disorder.
In October 2012, just two months after his hospitalization, news broke that Jackson was under criminal investigation for misuse of campaign funds. He won re-election that November and resigned just weeks later. The next February, he pled guilty to conspiracy to defraud his campaign of $750,000.
Since serving 22 months of a 30-month prison sentence, completing the rest of his time in a D.C. halfway house, and spending three years on supervised release, Jackson has taken an interest in the rights of felons and the presidential pardon power. He requested a pardon from President Biden and—along with former Trump attorney Michael Cohen—wrote an op-ed in The Hill after that request was denied, advocating for reconsideration.
This August, he shared a report that President Trump was considering pardoning Diddy, the former rapper who has been accused of sexual misconduct and sex trafficking. “I do not believe Democrats can compete with Trump’s use of the pardon power for high celebrity and high visible black men. It shows Trump’s willingness to do something that no Democrat will do,” he added in a comment under the post.
Pardons have been top of Jackson’s mind for years. In 2022, he posted: “Trump considers pardons for Capitol rioters. Biden remains silent on Pardons for 77 million debt paid felons.” And in 2023: “Dear President Biden, Hunter needs a full presidential pardon, but don’t we all? Especially if we have paid our debt to society in full?”
Digles said that Jackson’s experience with the criminal justice system will make him an advocate for others in the district who have served time in prison. “He has a unique perspective on this,” Digles said. “He’s laser focused on the pain and conversations with voters in the district.”
JACKSON IS ONE OF 12 CANDIDATES IN THE RACE, and faces a strong challenge from the left by state Sen. Robert Peters, who cut his teeth pushing for bail reform in Illinois. Peters has also put his stamp on a number of recent Illinois bills that challenge Trump’s agenda, like the 2019 Reproductive Health Act, which he co-sponsored.
“This is an immensely beautiful and diverse district, and it’s also very much a working-class district,” Peters told the Prospect when asked about his motivations to run. “[It] is a district where people are always on the knife’s edge when it comes to their health care, when it comes to their retirement and when it comes to their housing.”
In the district, 17.5 percent of residents live below the poverty line. Nearly half of residents are Black.
Peters pointed to the district’s experience during and after the Great Recession of 2008, when residents of the Second District were particularly vulnerable. “While the banks got bailed out, working-class Black folks in the South Side and south suburbs literally had the rug pulled out from under them,” he said. “We need to correct that, and that’s something we can do at the federal level.”
Peters’s proposed solutions to help the district’s working-class residents are mainstays of the progressive playbook: Medicare for All, regulating prescription drug costs, expanding Social Security benefits, and building more affordable housing.
He also has specific plans for the district. While Jackson has proposed opening a third Chicagoland airport in the south suburbs, Peters advocates for a Level 1 or 2 trauma center—the kind of hospital that is equipped to handle major emergencies like gunshot wounds or car accidents—in the same area.
I asked Peters if he’s worried that voters will have forgotten Jackson’s corruption, since he was convicted more than a decade ago, and will gravitate toward his familiar and powerful name. Jackson seems to be betting on this; he references his father on multiple pages of his website. (“Jesse Jackson Jr. believes we must come together to defend the freedoms that Dr. King, his father, and others in past generations risked their lives for,” his “About” page reads.)
“He’s a name. He’s someone who literally spent a bunch of money to live a lavish lifestyle while people are just trying to be able to go to the doctor,” Peters said. “What we’ve seen in the last year or so is a lot of people who’ve tried to make a political comeback off of their name and fail. This election cannot be about your name. It’s about what you’re going to deliver for the working people of the Second Congressional District.”