Ed Burke was born into the machine.

The son of a Democratic ward boss and 14th Ward alderman, the younger Burke grew up in a home steeped in Chicago’s particular street-level realpolitik: Smooth over potholes, fix up friends with patronage jobs, and make sure everyone who benefited knew how to vote — and for whom to vote.

At its zenith during Mayor Richard J. Daley’s era, Chicago’s political machine was an enormous self-sustaining network, and the city ran on it for decades. And by the time the younger Burke turned into an elder Burke, he’d become one of the greatest purveyors of machine politics in the city and the longest-serving alderman in Chicago history.

Fierce foes Ald. Timothy Evans, left, and Ald. Edward Burke listen during a Finance Committee meeting on Oct. 3, 1986, in Chicago. The two were principal combatants during the Council Wars, which ended in 1986.

Along the way, he’d earn infamy in the 1980s for trying to thwart every move of Harold Washington, Chicago’s first Black mayor, during “Council Wars,” pave the way for his wife to become chief justice of the Illinois Supreme Court, run the council’s Finance Committee like his own personal fiefdom and oversee an eponymous law firm that constantly put him into ethically questionable positions.

While Burke stood out among his aldermanic colleagues during his 54 years on the council, he now stands alongside dozens of them as another former alderman facing a federal public corruption trial. The Chicago machine he grew up with and worked to his advantage has atrophied.

Federal prosecutors have accused Burke of using his position as alderman to leverage the public’s business for his personal profit and, on Monday, Burke, 79, begins a high-profile trial over 14 federal charges in a racketeering case. The ex-alderman has pleaded not guilty, and his lawyers vow he will be vindicated. If he isn’t, he faces up to two decades in prison.

To win, Burke has spent nearly $3 million from his campaign funds on his lawyers’ legal fees since 2018, records show. Burke has also used his campaign funds to pay $165,000 in legal bills for co-defendant Peter Andrews Jr., who worked for years for Burke’s ward organization, and paid another $220,000 directly to Andrews for “consulting,” campaign records show. Andrews’ lawyers say that consulting payments also went toward Andrews’ legal fees.

It has taken years to get here. Even with initial charges hanging over his head, Burke rallied his organization, asked his Southwest Side constituents to stand by him and won reelection in 2019.

But as the case moved forward, he faced more charges, lost his ward committeeman post, saw his ward’s boundaries change, and declined to run for alderman one more time. Burke ended his historic tenure earlier this year, slightly undermining his long-running joke that aldermen only leave the City Council one of three ways: “The ballot box. The jury box. Or the pine box.”

At the height of his power, Edward M. Burke, who often dressed immaculately in pinstripe suits with flashy handkerchiefs tucked neatly into his breast pocket, knew exactly when to unleash his political sledgehammer to get his way and when to quietly undercut an opponent with the swift twist of a partisan scalpel. His clout paid off in ways big and small; after a snowfall, his block got plowed early and often.

Subtly burnishing his image as a cut above City Hall’s regular cast of mischief-makers, Burke portrayed himself as the white-haired dean of the council who often drew on his ethnic roots to quote the eloquent 18th-century Irish-born — but unrelated — statesman Edmund Burke.

Ald. Edward Burke, 14th, rides an elevator down from the second floor of City Hall after attending his final City Council meeting as an alderman on April 19, 2023.

But outside of his public persona, prosecutors contend, Ald. Ed Burke was little more than a self-interested street politician who made himself a little richer and a little more feared by embracing the timeworn aldermanic creed: Where’s mine?

Using Burke’s own words caught on tape, federal authorities argue that, compared with his outsize power, some of Burke’s misdeeds were shockingly small. Echoing schemes from the machine era, he threatened the Field Museum for ignoring his effort to get an internship for a political pal’s daughter, and he tried to shake down the owners of a Burger King in his ward to send their legal work to his property tax appeal law firm, they allege.

Most prominently, though, Burke allegedly tried muscling in on some property tax work for the $800 million renovation of the old main Chicago post office in the West Loop — and forcefully expressed his disgust when developers rebuffed him.

“As far as I’m concerned, they can go f— themselves,” Burke said in a secretly recorded October 2017 conversation.

Burke’s ire had been building, based on previously recorded discussions with Danny Solis, the 25th Ward alderman-turned-government-mole who chaired the council’s zoning committee.

In a January 2017 recorded call with Solis, Burke allegedly refused to help the Old Post Office’s New York-based chief developer through a regulatory maze until he met Burke’s demand for legal work.

“The cash register has not rung yet,” Burke explained on another recording.

Prosecutors alleged Burke even talked to Solis about getting the developer to financially “assist with the reelection” of his brother, state Rep. Dan Burke, who ultimately lost.

But Ald. Burke allegedly dropped perhaps his most memorable phrase of the Old Post Office saga when he asked Solis whether they were about to reel in the tax work for his law firm, Klafter & Burke.

“So did we land the, uh, the tuna?” Burke allegedly asked.

Chicagoans didn’t need a translator to know what he meant.

The oldest of three sons, Burke landed a position as a Chicago police officer and was soon assigned to a desk job at the Cook County state’s attorney’s office. A supervisor once warned investigators to take special care of Burke — after all, he was an alderman’s son.

In mid-1968, when Burke was 24, his father, Joseph, died of lung cancer. After a backroom power struggle, Burke took over as 14th Ward Democratic committeeman. His name reportedly was on a banner at the infamous Democratic National Convention in Chicago that year, his sign proclaiming Richard J. Daley as the “World’s Greatest Mayor.” Burke, working in plainclothes, said he wore a “suit, and not the uniform.”

Less than a year later, Burke stepped into the role he would play for more than half a century: 14th Ward alderman.

He quickly joined with Ald. Edward Vrdolyak, 10th, and other “Young Turks” in the early ‘70s as a modern counterpoint to Daley. They made waves by demanding more active roles during a so-called Coffee Rebellion, so named because the young aldermen held their meetings in the mornings. But they ultimately remained loyal to Daley.

When another alderman implied that Burke’s clout got him a spot in the Army Reserves during the Vietnam War, Burke threatened him in a backroom: “If you weren’t so old, I’d punch you right in the nose.”

Clearly ambitious, his dreams of moving into higher offices — mayor, Cook County Board president, Congress — repeatedly fell short. But his biggest knock-down, drag-out fight came in 1980 when he lost the Democratic primary for state’s attorney to Hizzoner’s son, Richard M. Daley.

Then came 1983, a year nothing short of seismic in Chicago politics as voters elected its first Black mayor.

Harold Washington was charismatic, progressive and far from beholden to the machine’s establishment Democrats.

Ald. Edward Burke, 14th, second from right, and Ald. Edward Vrdolyak, 10th, second from left, head to a meeting with Mayor Harold Washington on on July 2, 1985, at Chicago City Hall.

Burke and Vrdolyak saw Washington’s rise as an explicit threat and banded together, grabbing anti-administration headlines as the “two Eddies” who led the predominantly white ethnic “Vrdolyak 29″ bloc through the “Council Wars” that got so fiery Chicago was dubbed nationally as “Beirut on the Lake” during a time of escalating violence in the Middle East.

Burke was “the government side of the operation. Vrdolyak was the political side,” said Dick Simpson, professor emeritus of political science at the University of Illinois at Chicago who served alongside them as 44th Ward alderman in the 1970s. “Vrdolyak was the wheeler-dealer. Burke was, ‘Let’s run this government the way we want it to run.’ ”

The battles against the first Black mayor of a historically segregated city were inevitably racially motivated, and Vrdolyak was not shy about “stirring up racial unrest wherever he could,” according to Washington press secretary Alton Miller’s book “Harold Washington: The Mayor, the Man.”

“(Vrdolyak is) not a racist. He’s a bully,” Miller recalled Washington telling him. “He’ll use race, hell, he’ll use anything, he’ll use his own grandmother to get what he wants. … Amoral, yes. Racist, uh-uh. Burke is a racist.”

A few years after Washington’s death, Burke told the Tribune that “nothing could be further from the truth.”

“If he felt that way, I feel badly about it,” he said. “But frankly we had a number of very pleasant exchanges despite the occasionally vituperative nature of the political war that raged on.”

U.S. Rep. Danny Davis, who at the time was a West Side alderman aligned with Washington, recalled the mayor would say, “‘There’s no hope for Ed Burke. … He’d say, ‘Well, you can sometimes negotiate a little bit with Vrdolyak, but Ed Burke is Ed Burke, and that’s what he’s going to be.’

“I didn’t necessarily think that the individuals were racist, but I did think that they were not averse to using the race card as part of the implementation of their political intent,” which included maintaining patronage and political power, said Davis, a Democrat.

Simpson said Burke grew up in a heavily white neighborhood during times of overt racism, but thinks Burke’s personal views likely evolved over time, noting that Burke and his wife eventually adopted a Black child.

Anne Burke, in an episode of Democratic consultant David Axelrod’s “The Axe Files” podcast just a few months before federal agents raided Ed Burke’s offices, suggested that if Washington had lived, he might have seen the alderman’s views progress.

“He knew Ed at a time that was tumultuous. If he were alive today, then he knows and he could know that people can learn if they listen and if they grow,” she said.

Even so, Ald. Burke’s particular views on ethnicity will likely be highlighted at trial.

In a recorded conversation about the Old Post Office matter, Burke said the developers would only “work with Jewish lawyers.”

“Well, you know as well as I do, Jews are Jews, and they’ll deal with Jews to the exclusion of everybody else unless … unless there’s a reason for them to use a Christian,” Burke said.

Burke’s power over City Hall suffered a setback when a federal court ordered changes in ward boundaries that allowed more Washington allies to join the council. Once Washington was reelected in 1987, Burke lost his Finance Committee chairmanship. He regained it when Richard M. Daley was elected mayor in 1989, two years after Washington died in office. Burke kept the post until 2019 after he was hit with federal charges.

Mayor Harold Washington and Ald. Edward Burke put aside their political differences as they marched together in the sixth annual 63d Street Christmas Parade on Nov. 23, 1985.

Undoubtedly, Burke would rather be remembered for feel-good resolutions like declaring Mrs. Catherine O’Leary and her cow innocent of starting the Great Chicago Fire of 1871, pressing for smoking bans and becoming the unofficial council historian.

“In politics, especially amongst the Irish, there’s always infighting. Ed Burke was always on the other team,” said James “Skinny” Sheahan, who worked on multiple campaigns for Richard M. Daley as far back as his successful state’s attorney race against Burke. “But if anybody wrote a true history of Chicago, there is nobody in the history of Chicago that has helped more people than Ed Burke.”

Still, Burke’s career has been dogged by questions about potential conflicts of interest, including his property-tax law business and his unabashed support of his wife.

With the alderman cheering her on, Anne Burke secured appointments to fill vacancies on the appellate court and Illinois Supreme Court. She later won elections to those posts, but the appointments gave her a leg up. Though she is an accomplished judge, Anne Burke’s career certainly was not hurt because her husband long headed the judicial slate making for the Cook County Democratic Party, a place where endorsements can make or break candidates in the traditionally low-profile contests.

She became the state high court’s chief justice five months after her husband’s federal racketeering indictment and ended her three-year term as the head of the court last year. She retired from the court on Nov. 30, 2022.

For decades, Ald. Burke dismissed a variety of awkward issues with a wit that came with an all-knowing but sometimes-deceptive nod of his head. Even when a telephone caller could not see his face, it was easy to imagine the alderman’s comments came with a smirk.

When his wife looked into forming a coalition of women to snag a riverboat gambling license in the early 1990s, Burke didn’t flinch about a potential conflict. Sure, his City Council committee was examining Chicago’s efforts to land a casino. But he would not benefit if she profited, he said, because “she would be doing it as her own person.”

“Don’t you understand?” he said. “What’s hers is hers and what’s mine is hers.”

His sweet deals and potential ethical lapses tended to draw headlines.

“He was a classic example of walking conflicts of interest,” said former Ald. David Orr, 49th, who was interim mayor for a week when Washington died and later Cook County clerk for 28 years.

Orr took exception with how Burke served as an alderman representing citizens of Chicago but made money as a lawyer causing the “little guy, the little stores” to pay more in property taxes because he’d win tax reductions for large property owners, such as for former Republican President Donald Trump’s downtown skyscraper.

Throughout his career, Burke has regularly been in the middle of ethical controversies: He admitted to voting on legislation affecting Midway Airport while his firm worked for the airport’s main tenant at the time, Midway Airlines; he earned six-figure legal fees from a developer whom Burke worked for behind the scenes and who got a $1.2 million subsidy from City Hall; and he once got fined $2,000 by the City Board of Ethics for using “improper influence” in helping a tax client.

In 1987, the Tribune revealed Burke’s involvement in a sweetheart real estate deal in Wisconsin known as the Honey Bear Farm.

A subsidiary of Carson Pirie Scott & Co. had sold an interest in prime Wisconsin real estate to a group that included Burke and then-Ald. Terry Gabinski, 32nd, while the company was earning millions of dollars from a no-bid city contract that Burke and Gabinski voted to approve.

In 2011, a Tribune/WGN investigation found Burke helped a retired lawmaker cash in on a pension windfall. Former Democratic state Rep. Robert Molaro of Chicago worked only one month in 2008 as an aide to Burke, wrote a 19-page report and collected $12,000. The pension formula annualized that one-month paycheck and allowed Molaro to nearly double his $64,000 a year state pension to six figures.

Following the 2018 FBI raid on Burke’s office, the Better Government Association and WBEZ-FM reported Burke recused himself 464 times over eight years from council votes that ranged from major bond deals to zoning changes.

Burke’s racketeering case is far from the first time authorities investigated the alderman and his associates.

The feds sought records from Burke’s Finance Committee in 1995 as part of Operation Haunted Hall — a probe in which 39th Ward Ald. Anthony Laurino’s daughter, Marie D’Amico, pleaded guilty to holding ghost jobs with the Cook County clerk’s office, sheriff’s office and Burke’s Finance Committee, purportedly overseeing workers’ compensation claims, federal authorities said at the time.

Back then, Burke blamed a dead man — Horace Lindsay, D’Amico’s Finance Committee supervisor — for forging time sheets to cover her behavior.

“I don’t supervise the personnel,” Burke said then. “Do you expect I should know where everybody is, all 75 or 80 people or whoever’s there?”

In late 1997, Burke and 11th Ward Ald. Patrick Huels, Daley’s council floor leader at the time, received federal grand jury subpoenas for campaign finance records and payments awarded by the Finance Committee and the Transportation Committee, which Huels chaired.

Huels resigned after admitting he borrowed $1.25 million from a Daley friend, Michael Tadin, who also was a city trucking and hauling contractor. The loan came as Huels’ firm, SDI Security Inc., faced a federal tax lien of nearly $1 million and a backlog of overdue city head taxes.

Burke served as secretary of the company for nearly five years but had left before the tax troubles emerged, according to the Chicago Sun-Times.

Unlike Huels, who faced pressure to quit to minimize the blowback on Daley, Burke had his own political organization to weather the calls for his resignation. A defiant Burke, refusing to give up his chairmanship of the Finance Committee, quoted the late Cardinal Joseph Bernardin, who was falsely accused of sexual abuse.

“My faith reassured me that the truth was all that I had and all that I really needed,” Burke said, quoting Bernardin’s book, “The Gift of Peace.” “It would be my rod and my staff through the dark valleys of the months ahead.”

The next year, federal agents subpoenaed records of payments to a lawyer working for Burke’s Finance Committee on claims filed in work-related accidents.

In 2012, then-city Inspector General Joseph Ferguson sought records related to the workers’ compensation program, but Burke denied access, contending the records fell outside the watchdog’s jurisdiction.

A federal grand jury issued subpoenas for the program’s records dating back to January 2006, similar to a prior federal request. But nothing appeared to have come of those inquiries.

Burke’s world exploded Nov. 29, 2018.

Federal agents raided his City Hall suite, covered his office’s glass entryway with brown butcher paper and carted out boxes, computer equipment and other items detailed by a search warrant.

The raid took place the same day his wife was sworn in to a new term on the Illinois Supreme Court — a strange juxtaposition even for Illinois politics.

A police officer walks past the brown-paper-covered glass door and windows of Ald. Edward Burke's Chairman Committee on Finance office in City Hall on Nov. 29, 2018.
Ald. Edward Burke returns to his Southwest Side home on Nov. 29, 2018, after federal raids on his offices earlier in the day.

As FBI agents rummaged through Burke’s offices, the alderman attended a luncheon at the Chicago Yacht Club celebrating his wife’s new term on the court, where she would soon rise to chief justice.

A criminal charge of attempted extortion was unsealed just weeks later, in January 2019. While Burke stepped down as Finance Committee chairman, he still easily won reelection in February thanks to a strong ward organization and loyal constituents.

“Oh, my God. They rallied behind him,” said Tom Manion, who knocked on doors as an assistant precinct captain in Burke’s 14th Ward and had a daughter who worked for Burke.

But that love only carried Burke so far.

The scandal quickly grew into campaign fodder for mayoral candidate Lori Lightfoot, a former federal prosecutor.

Lightfoot hammered opponent Cook County Board President Toni Preckwinkle, who suffered from revelations that Burke squeezed one of the Burger King owners to send her a campaign contribution. Lightfoot won, and, after taking office, she faced off with Burke during her first City Council meeting.

In a memorable showdown, after Burke rose to test Lightfoot on a minor point, she cut him off and left him slack-jawed.

“Alderman, I will call you when I’m ready to hear from you,” Lightfoot said, an exchange played repeatedly on local news outlets.

Ald. Edward Burke, 14th, speaks May 29, 2019, at Lightfoot's first Chicago City Council meeting. Shortly after, Lightfoot cut him off and said, "I will call you when I'm ready to hear from you."

The next day, Burke was hit with the full 14-count indictment.

The unrelenting string of events sent the old-school Democrat’s political fortunes into a downward spiral.

Having already ended his partnership with his law firm, Burke lost his bid to stay on as Democratic ward committeeman in 2020 and as new city ward maps were redrawn that weren’t favorable to Burke, thanks in part to Lightfoot, he chose not to run for reelection as alderman in 2023.

In addition to fellow defendant Andrews, Charles Cui is also charged. He’s accused of hiring Burke’s law firm in exchange for the alderman’s help with a sign permit and financing deal for a project in the Portage Park neighborhood.

If Burke is found guilty, he will join a club of aldermen convicted of corruption. That includes his old colleague Vrdolyak, who pleaded guilty twice — most recently in 2019, to a federal tax charge alleging he obstructed an IRS investigation.

The fifth anniversary of the butcher-paper raid is expected to land in the middle of a trial that is scheduled now to roll into December.

Burke’s only way out of his unrelenting spiral may be winning an acquittal.

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