In Praise of Barack Obama
He rose from the muck of a corrupt political machine in Chicago to become a template of grace and decency
Do you know how hard it is to be an Illinois politician not steeped in corruption? It’s like being the one declawed lion in the lion’s den. It’s like cosplaying Mr. Spock at a Star Wars convention. It’s like being the one honest man scavenging the ruins of the East Wing of the White House.
Sometimes, it’s not about politics.
Barack Obama’s politics are far to the right of mine. Some of his policies, such as drone strikes in Afghanistan, made me want to scream into the night. As a president, he was a centrist. I most certainly am not.
If he emerged from a hot tub time machine into the 1970s, he’d be a moderate Republican like two other former Illinois senators, both Republican: Everett Dirksen and Charles Percy.
Sometimes, it’s not about politics.
Just before he won the presidential election, I believed him when he said he was a blank slate. That was typical centrist posturing, but it was honest. I squirted a few tears of joy on that election night. I had no misgivings.
Obama possesses a core decency that has been missing from American politicians for 250 years. He’s a unicorn. He’s the family man that no Republicans, who once claimed to own the mantel of family values, can even speak of in their current fugue of malfeasance, hate, and sex crimes as they continue to fall over each other in service of a man whose name is said to appear one million times in unredacted versions of the Epstein files.
Obama’s integrity is even more remarkable when you consider the nature of Illinois politics during his ascension.
If he’s a crook, he’s the sneakiest summabitch whoever lived and has earned every penny of his ill-gotten wealth.1 So even then, I’m giving him his props.
Also? I think we all know he’s not. And this is part of what makes him special.
Illinois politics was steeped in corruption during Obama’s Illinois political career
One of life’s great mysteries is: How did he do it? I’ve never read an Obama biography or autobiography except for parts of Dreams from My Father: A Story of Race and Inheritance. Maybe the answers lie in one of his other books.
I won’t try to explain it here beyond some (mostly) guesswork at the end of this essay. Instead, I’m going to describe the cesspool from which he came so that you can marvel at his achievement and better appreciate how remarkable his political journey was.
In Illinois, 1,913 public officials ended up behind bars after federal trials in Illinois’ Northern District between 1976 and 2012.2
Four out of nine governors before current governor JB Pritzker found their way to the hoosgow.
Thousands of dollars were found in Secretary of State Paul Powell’s shoe boxes and various other hiding places such as strong boxes and briefcases in the 1970s.3
Illinois’ career Speaker of the House, Michael Madigan, was sentenced to seven years in prison in 2025 on ten felony counts for federal bribery and wire fraud. He was a fixture of Illinois politics during Obama’s days in Illinois politics, but Obama miraculously avoided the Madigan corruption machine.
Chicago and Illinois had already developed a reputation as a wild place for unrestrained political corruption under the Daly Machine, led by Mayor Richard J. Daley, who ruled Chicago with an iron fist from 1955 until 1976.
As Chairman of the Democratic Party, all roads to political success ran directly into his office, where favors, bribes, and ultimatums decorated the walls like Trump gold.
Daley was never convicted of anything. His son, Richard J. Daley, who was also a Chicago mayor, seemed much less interested in harboring corruptioneers. But hundreds of people surrounding Daley Sr. were jailed for various corrupt practices.
With that culture firmly in place, subsequent political bosses like Madigan fought to develop their own fiefdoms in the wake of the Daley empire, like Ptolemy, Seleucus, and Antigonus carving up the Alexandrian empire after Alexander the Great’s death.
Madigan came out on top, but the entire state became a cauldron of relentless crime and graft, with hundreds of corrupt politicians scrambling for as many illicit proceeds as they could get their hands on.
Authors Dick Simpson and Tom Gradel, who co-wrote Corrupt Illinois: Patronage, Cronyism and Criminality, reported in that book that such a rate of corruption is matched only by Louisiana and Washington, D.C., where the population of affected citizens is much smaller.
I would argue that no jurisdiction in America can match the graft of the Illinois and Chicago Democratic machine.
I would also argue that Obama’s influence, in addition, of course, to more than a thousand politicians scooped out of the political swamp and thrown into federal prison, has led to significant reforms that have transformed Chicago and Illinois politics into something more benign. Today, Illinois more closely resembles the common kind of political graft we see in other states governed by one-party rule, rather than rampant crime everywhere, all the time.4
The gauntlet of Chicago’s Democratic machine
The gauntlet of the Illinois Democratic machine’s corruption that Obama had to work through is too large for a minimal Substack like this to fully document. Entire books have been written on the subject. I’ll cover a few highlights so you can get a sense of the political environment Obama had to navigate.
Michael Madigan
Madigan built an empire. An empire of crime. Not in the way Trump has. Not quite as much in your face, although he didn’t make much of an effort to hide things.
Madigan was Speaker of the Illinois House of Representatives from 1983 to 2021, except from 1995 to 1997, when Republicans managed to sneak in a couple of years as the state house’s majority party. He was the main tollbooth through which all Illinois politicians were required to pass.
The gates of the tollbooth were operated by cigar-chomping men with the kind of criminal connections that made federal prosecutors’ heads spin.
U.S. District Judge John Blakey said, while sentencing Madigan, that he was the “central command post” of a massive, ongoing bribery operation between mega-utility Commonwealth Edison and Illinois politicians lining up to grease their palms for favors.
Blakely wrote:
“It was a nauseating display … of perjury and evasion. You lied, sir. You lied. You did not have to.”
But the Commonwealth Edison bribery case was notable not for its corruption, but as being the one time Madigan was caught with his fingers in the cookie jar. He had established a sparkling reputation as a local prince of corruption long before his indictments.
Federal prosecutors were unable to obtain convictions on Madigan’s (alleged) full criminal career that most Illinois political observers would describe as a “yearslong criminal enterprise to enrich himself and his political allies,” in the words of pre-Trumpian CBS News.5
In all, Madigan and co-conspirator Michael McClain originally faced a 23-count indictment for racketeering, conspiracy, bribery, wire fraud, and extortion covering the majority of his years as speaker. Federal prosecutors were surely disappointed that they couldn’t obtain convictions on all of them.
Jurors also convicted Madigan on three counts of wire fraud for his attempt to buy a state board seat for Chicago Alderperson Danny Solis, who was himself accused by the FBI of funnelling hundreds of thousands of dollars from campaign funds into his personal bank account.
Chicagoans greeted Solis’s behavior with a shrug. It was business as usual; a typical alderman (that’s what they were called in those days, since politicians were mostly men).
Most importantly, Madigan was essentially the party boss during Obama’s Illinois political career.
Obama being Obama, he wound his way through the Madigan muck with a clever grace, which I’ll get into later.
Rod Blagojevich
Where do I begin?
Former Illinois Governor Blagojevich is also a unicorn of sorts. Somehow, he managed to transcend the criminal underworld of Illinois politics to create his own unique brand of what might best be called “criminal buffoonery.”
He went to prison like any good Illinois governor should, and was accused of a world of pay-to-play schemes, but America had a favorite: Using his office as governor to sell the United States Senate seat that Obama vacated, after winning the presidency, to the highest bidder.
It was such a terrific blend of criminality, brazenness, and silliness that Americans very nearly developed a sort of fondness for the guy, enough so that when the Grifter-in-Chief pardoned him in 2025, many of us felt a sense of relief that America’s silliest governor copped some forgiveness within the scope of this cold, cruel world.
Blagojevich served as governor from 2003–2009, the final two years of Obama’s term as an Illinois Senator (not U.S. Senator from Illinois, but instead a member of the Illinois Senate).
One reason Blagojevich was able to retain some affection from voters despite his criminality is that he was a progressive governor who helped set the template for Illinois’ current governor, JB Pritzker.
Blagojevich was ultimately convicted on 17 corruption charges. All Obama needed to do to avoid any accusations of connections with Blagojevich was avoid walking into the governor’s office for a chit chat, which Obama studiously did.
Edward Burke & Jesse Jackson Jr.
In the grand scheme of Chicago corruption, these two were minor players. But they were contemporaries of Obama. The temptation to hang with Jesse Jackson Jr., especially, must have been great, considering Jackson’s father’s legacy.
Jackson Jr., who was a U.S. Representative from 1995 to 2012, pleaded guilty in 2013 to wire and mail fraud for redirecting campaign contributions for personal use, primarily the purchase of luxury goods. He served 30 months in prison.
Burke was a career Chicago alderman, serving from 1969 to 2019. Like Madigan, he had a long, distinguished history as a career criminal whose antics were as well known to Chicagoans as Wrigley gum. Like any good Chicago Democrat, he was convicted of racketeering, extortion, and bribery.6
He was a local kingmaker, but Obama avoided Burke like he was a nasty pox specializing in explosive diarrhea.
Antoin “Tony” Rezko
There comes a time in most political careers when the lizard pays a visit and invites you into his den to dine with him on an endless feast of corruption. For history’s worst president, that moment came when he was a young real estate carnival barker in New York City chasing Black people out of his tenements. One day, one of Joseph McCarthy’s sleazy lawyers, Roy Cohn, paid him a call, became his mentor, and the rest is history.
For Barack Obama, the lizard was a real estate developer named Antoin “Tony” Rezko.
Rezko ran a company, Rezmar Corporation, that interviewed Barack Obama when he was still a student at Harvard, where Obama was president of the Harvard Law Review. Luckily for us, Obama didn’t get the job, and the young, ambitious scholar instead took a job with a law firm that focused on civil rights litigation, Davis, Miner, Barnhill & Galland.7
Although Rezko didn’t offer Obama a job, he did recognize some of Obama’s obvious traits and strongly encouraged him to look into a political career.
Whether Rezko had the same kind of intent as Roy Cohn did toward Trump is impossible to know. But it’s fair to guess that when someone encourages your calling, and then you become successful at that calling, a soft spot develops towards the person encouraging you.
All indications point, however, to Obama always taking counsel with himself first, and never letting one person control his destiny or play too large a role in his success.
This may have been his superpower as a young man, and it saved him from the snares that Illinois politicians might have led him into.
Rezko was a political huckster who made one of the first contributions to Barack Obama’s earliest campaign efforts via two food companies. It was a modest contribution, $2,000, but Obama was running for small potatoes: a seat in the Illinois Senate. Nobody knew who he was. Nobody cared.8
Although they remained on friendly terms, Obama never allowed himself to get caught up in Rezko’s world of graft, which eventually included the usual mix of wire fraud, bribery, money laundering, and extortion, for which he was indicted in 2006 and eventually convicted.
Later, Rezko grifted his way onto Obama’s U.S. Senate campaign finance committee, which eventually pulled in $14 million in campaign contributions, but he wasn’t the top dog there, and there are no known improprieties.
Reporters tried to cast shade on a real estate transaction Obama made with Rezko after Obama cashed in on book royalties. Obama purchased a home next to a lot owned by Rezko’s wife. The accusation: Rezko sold a ten-foot parcel of his wife’s land to Obama at a higher than assessed value to make Rezko’s wife’s land less attractive to local developers.
A bit of a stretch to call that corruption, but Obama conceded the point anyway in later interviews, expressing regret over the deal.
Can you imagine the current occupant of the Oval Office fretting about such things?
Reporters, and even Hillary Clinton (during their 2008 presidential primary campaign), tried to tie Obama more closely to Rezko, but failed.
Rather than view his relationship with Rezko from the lens of corruption, it’s more useful to view it from the larger field glasses of a young man veering out of corruption’s way, but being smart enough to slap the occasional crooked shoulder so prevalent in Chicago politics.
Rezko was as close to corruption as Obama ever tread, and that wasn’t very close.
Rahm Emanuel
Rahm Emanuel was the perfect partner for Obama during and before Obama’s presidency. He has just enough Chicago in him to be dangerous, but he doesn’t appear to possess the penchant for corruption most other Illinois Democrats have.
Personally, I think this is because he was a ballet dancer in his youth. He turned down a dance gig with the Joffrey Ballet in favor of politics, and somehow danced his way through Chicago politics, cozying up with Barack Obama enough to become Obama’s Chief of Staff after Obama was elected.9
Emanuel’s biggest crime is that he’s a Clinton corporatist. He started his political career progressively enough, as a political operative for Paul Simon (the Illinois Senator, not the singer/songwriter).
Later, he worked for Clinton, where he became deeply involved with NAFTA, which eventually became a war cry for MAGA, but was also frowned upon by many on the left.
Some would also call Emanuel a Zionist, but I don’t like getting into those arguments because that part of the world was ruined by Europeans after World War Two more than it was by the people caught in the conflict created by the Palestinian Mandate imposed by Great Britain and others.
Emanuel is certainly Jewish. His middle name is “Israel,” after all, and his father was born in Jerusalem, where he took a bullet during Arab protests for Irgun, a Zionist paramilitary organization.
Emanuel wants to be your next president, an unlikely event, mostly because his past associations with Israel will obliterate10 him during the Democratic primaries.
He’s now a fierce critic of Netanyahu.11 He delivered a speech earlier this month in Tel Aviv urging the withdrawal of U.S. aid unless Netanyahu’s policies are rejected by Israeli voters, but this is a bit like someone snatching a winning lottery ticket from its owner as she hands it to the clerk and then laying claim to the prize.
But during the Obama years, Israel wasn’t drawing the same attention as it is now, even though its apartheid-like policies against Palestinians were firmly entrenched. Israel still had the sympathy of much of the world, leveraged by support for those who argued that it was a nation surrounded by hostile neighbors.
In Illinois, Emanuel served as a political mentor of sorts for Obama, but he also served as a guy who’d take some of the punches aimed for Obama’s head, a task he also performed as Obama’s Chief of Staff.
How did Obama escape all that?
Picking the right people to chill with has always been one of Obama’s many skills. Rahm Emanuel might not be my idea of progressive politics, but he was a handy torch for Obama to carry into meetings with power brokers, and has stayed out of trouble.
When Obama found mentors, they were clean. Obama served as the main driver of a shadow effort by U.S. Democratic Senator Paul Simon, a man considered to have been of pristine integrity, to force state legislatures to put together a set of campaign ethics laws for Illinois. The result was a new law called the Gift Ban Act. According to the political publication Stateline:12
The 1998 law prohibited politicians from using their campaign funds for personal use, banned fundraisers in Springfield during legislative sessions and required candidates to file their fundraising information online, so the public could see who was paying for a campaign before the election.
Nobody was likely more important as a mentor than Emil Jones Jr., who was the President of the Illinois Senate when Obama arrived. Jones was constantly in Michael Madigan’s face, but, more importantly, Jones acted as an armour coating for Obama when Obama was still green and learning the state’s political ropes as an Illinois senator.
He moved Obama through the line of hands you must shake in Illinois when Obama ran for the U.S. Senate. Obama needed Jones’ help, because he most certainly wasn’t going to get it from Michael Madigan, who feared Obama’s reform efforts.
Madigan campaigned for Obama’s opponent in the Senate primary, Dan Hynes, instead. This led to Hynes getting 63 percent of the vote in Madigan’s home 13th Ward of Chicago, to Obama’s 15 percent. But Jones said to Obama, “Don’t worry, we’ve got this.” Obama won the primary, and the rest is history.13
The combination of clean mentors and active efforts at election and political reform resulted in two simultaneous messages from the young, charming, ambitious, and funny politician from Chicago, Hawaii, and, through ancestry, Kenya: “I’m an up-and-coming politician you need to pay attention to, and I’m saying ‘no’ to the land mass of Illinois corruption.”
After he became the president of the United States, corruption in Chicago suddenly became taboo. Not nonexistent, but no longer the game that must be played to advance a political career. Obama became a new template. Citizens began to demand more Obamas and fewer Madigans.
What is happening on a national scale today will ultimately land in the same place. Americans are seeing Chicago-style corruption on a nuclear scale.
But they’re also furious. The blowback will send hundreds of politicians to jail when Jack Smith or someone like him becomes Attorney General/Jailer during the next administration.
Maybe, if we’re lucky, we’ll also get a new Chief Justice of the Supreme Court named Barack Hussein Obama.
Thanks for reading!
Footnotes
Obama made almost all his money from book royalties.
Lowenstein, Jeff Kelly. “Illinois and Integrity: A Strange Tale and Curious Mix.” Center for Public Integrity, June 5, 2015. https://publicintegrity.org/politics/state-politics/illinois-and-integrity-a-strange-tale-and-curious-mix/.
Associated Press. “Southern Illinois Home of Paul Powell, the ‘Shoebox Scandal’ Politician, Could Soon Be Sold.” WTTW News, February 19, 2024. https://news.wttw.com/2024/02/19/southern-illinois-home-paul-powell-shoebox-scandal-politician-could-soon-be-sold.
Under the fine tutelage of Attorney General Ken Paxton and Governor Gregg Abbott, Texas is seizing the title of most corrupt state in the nation.
Feurer, Todd, Chris Tye, and Sabrina Franza. “Michael Madigan, Former Illinois House Speaker, Convicted on 10 Corruption Counts, Acquitted on 7 Others.” CBS News. CBS Chicago, February 12, 2025. https://www.cbsnews.com/chicago/news/verdict-reached-corruption-trial-former-illinois-speaker-mike-madigan/.
Hagerty, Jim. “These Are the 10 Best-Known Illinois Public Officials Convicted of Crimes.” MyStateline | WTVO WQRF News, Weather and Sports, June 23, 2025. https://www.mystateline.com/news/illinois-corruption-10-officials/.
Morain, Dan. “Obama’s Lawyer Days: Brief and Not All Civil Rights - Los Angeles Times.” Archive.org, 2024. https://web.archive.org/web/20080410052901/http://www.latimes.com/news/politics/la-na-obamalegal6apr06,0,26672.story.
Contributors to Wikimedia projects. “American Businessman, Political Fundraiser, Restaurateur and Real Estate Developer.” Wikipedia.org. Wikimedia Foundation, Inc., October 15, 2006. https://en.wikipedia.org/wiki/Tony_Rezko#Ties_to_Barack_Obama.
Source for most of the Emanuel info:
Wikipedia.org. “Rahm Emanuel - Wikipedia,” 2019. https://en.wikipedia.org/wiki/Rahm_Emanuel.
And my always questionable memory.
By “obliterate,” I don’t mean the Trump version of the word, which means “to not do any significant damage.” I mean “obliterate” in the real sense of the word as defined by Webster’s dictionary: “to remove utterly from recognition or memory, to remove from existence: destroy utterly all trace, indication, or significance of.” In a political sense, of course.
Halbfinger, David M. “In Israel, Rahm Emanuel Calls for End of Unconditional U.S. Support.” The New York Times, July 7, 2026.
🎁 Ruminato Gift Link https://www.nytimes.com/2026/07/07/us/politics/rahm-emanuel-speech-israel.html. 🎁
Vock, Daniel C. “Obama’s Record in the Illinois Senate.” Stateline, August 25, 2008. https://stateline.org/2008/08/25/obamas-record-in-the-illinois-senate/.
Madigan became an active supporter of Obama’s presidential campaign.
This was excellent Charles! I learned so much by reading it. Thank you!