Chicago has had enough of the Jackson family
Years after it was assumed that he had vanished forever from the electoral scene, Jesse Jackson Jr., a Chicago Democrat, might soon enter the race to replace Robin Kelly as congressman of Illinois’ 2nd congressional district.
Kelly, in turn, succeeded Jackson, who resigned two weeks after being reelected for the seventh time in 2012.
In July, the Friends of Jesse Jackson Jr. for Congress 2026 Exploratory Committee was formed.
Kelly is running for the U.S. Senate seat currently held by another Democrat, Dick Durbin, who is retiring.
The district, as was explained in an earlier Chicago Contrarian article, is another gerrymandered abomination. It runs from Hyde Park on the South Side past Danville deep in central Illinois. The neighboring 1st District is represented by Jonathan Jackson, Junior’s brother.
Younger voters who have moved to Chicago recently might not be familiar with Jesse Jackson Jr., although it’s likely they know about his father, the Reverend Jesse Jackson Sr., a well-known civil rights leader and the longtime head of the Rainbow PUSH Coalition — although many others view him as a conniving grifter.
It has been said about Governor J.B. Pritzker that he was born on third base, and he thinks he hit a triple. Regarding Junior, it is fair to say the same thing, only his father extorted that third base in one of his many shakedown schemes.
As for seasoned Illinois voters, they might appreciate a refresher course on Junior.
Mr. Jackson’s CV, in brief
In 2013, Jackson pleaded guilty in federal court to misusing $750,000 in campaign funds to purchase a dazzling array of personal items, including Martin Luther King memorabilia, two mounted elk heads, a gold-plated Rolex watch, an Eddie Van Halen guitar, and a Michael Jackson fedora. Jackson’s then-wife, Sandi, who was serving as the alderman of Chicago’s 7th Ward, pleaded guilty to a single tax charge for her role in the swindles. Jesse served a year-and-a-half sentence in prison and Sandi, non-currently because the couple was raising young children, was imprisoned for 11 months.
During his time in Congress, Jackson developed a reputation for three things — his reliably left-wing voting record, his meager legislative accomplishments, and never missing a roll call for a House vote — that is until June 2012, when he checked himself into the Mayo Clinic for bipolar disorder.
Illinois law bans felons from elected office but there is not a federal law blocking felons from seeking a House or Senate seat. For instance: Mel Reynolds, Jackson’s ex-con predecessor in the 2nd, ran in the same special election primary in 2013 which Kelly won.
Blago
Jackson’s name was first sullied four years earlier when he was identified as Senate Candidate 5 in the federal criminal complaint of then-Governor Rod Blagojevich. It was alleged Blago schemed to sell the vacant U.S. Senate seat previously held by Barack Obama. Although Jackson denies involvement, Raghuveer Nayak, a longtime fundraiser his campaign and the owner of several surgery outpatient centers, proposed to raise $6 million for Blagojevich’s campaign fund if the governor appointed Junior to the Senate seat.
Later, it was disclosed that Nayak paid for two flights from Washington, D.C., to Chicago for a female acquaintance to meet with Jackson.
In 2015, Nayak pleaded guilty to tax fraud.
During his shadow campaign to become a senator from Illinois, Jackson opined: “I am the ideal, the best and the most qualified person.”
Humility has never been a strong Jackson family trait.
Junior even recruited comedian Bill Cosby — who would face his own serious legal troubles several years later — to plead with Blago for that appointment. Cosby was even coached on how to pronounce Blagojevich’s name.
2nd district voters — do you want more of this chicanery?
Blago seemed frosty to the idea of appointing Jackson, but he still met with him to discuss the seat. However, the morning after the meeting the governor was arrested and a month later Blagojevich was impeached and removed from office.
Shortly after Sandi's release from prison, Jesse, citing the usual “irreconcilable differences,” filed for divorce after 25 years of marriage. It was a messy split, and amid Sandi’s charges of infidelity by Jesse, it was revealed in 2017 that Junior was receiving $138,400 in annual federal benefits — $100,000 in worker’s compensation because of his bipolar disorder and the rest from Social Security disability payments.
Junior today
For the past year, Jackson has worked as a radio host for KBLA 1580 AM in Los Angeles. The Jesse Jackson Jr. Show, which is available in podcast form, is 50,000 watts of intellectual dead air.
His show is a brutal listen. Jackson views himself as a philosopher. Yet, he's more like Don Knotts' bombastic Barney Fife character on the old Andy Griffith Show — someone who is not nearly as smart as he thinks.
During on show in August, Jackson emitted this fatuousness:
“I’m not so sure that we see it as the tool of interconnectivity where everything comes into the present in that moment and you have the opportunity to vote for justice or to vote for injustice, to vote for housing or to vote for homelessness. You have that power in your one vote, but you must have an understanding, as Dr. [Azza] Karaam said, of interconnectiveness and the mutuality.”
Here's another Jackson mental misfire. It was part of a discussion about the philosopher Georg Wilhelm Friedrich Hegel from another August episode.
“Every response to that thesis or the antithesis has some truth to it. The reconciliation of that in the form of a synthesis creates a new truth, but at the same time that it creates a new truth, it creates a new thesis, and therefore the process creates a new antithesis, and such is the process of life, right?”
Yeah man, whatever you say, Junior.
The 2026 race
If you think that a Jackson victory in next spring’s Democratic primary is a longshot, you are wrong. While name recognition tends to favor established candidates in early polls, not including Jackson, there are seven declared Democratic candidates for the March 17 primary, including state Senator Robert Peters (13), the midwife of the no-cash bail SAFE-T Act, who was profiled earlier this year in Chicago Contrarian.
In an August Lester & Associates poll on the 2nd congressional district primary, which was paid for by the Jackson exploratory committee, Jackson came out on top with 21 percent. While 43 percent of those polled are undecided, the candidate with the next strongest showing in the Jackson-funded poll is Water Reclamation Board commissioner Yumeka Brown at 11 percent. There is some good news from that survey. Peters, “Mr. SAFE-T Act,” is favored by only four percent of respondents.
In an election with a large field of candidates, Jackson’s 21 percent, if that number holds, just might be enough for him to win. Also, keep in mind, of late, Democrats and their media allies have backed away from what they deem as negative campaigning. So, it is up to moderates and conservatives to blow the whistle on leftist indiscretions. And Jackson has plenty of them.
Because of the way the 2nd district is drawn, the Democratic nominee will be the overwhelming favorite to win next autumn’s general election.
Currently, Illinois’ House delegation consists of 14 Democrats and three Republicans. Of those Democrats, it's possible in 2027 that two of those Dems will be Jacksons.
For Illinois and the nation, that will be the wrong kind of Jacksonian democracy.
