What the Trump Administration Can Do for Chicago

February 3, 2025

It will fall on the Trump White House to stabilize the Windy City

The American public’s response to the election of New York businessman and former President Donald Trump has been mixed. To nearly half of the country, the news Trump was victorious in the presidential election was greeted with fear, anxiety, and frustration. In contrast, to the other half of the country, the return of Trump to the White House is a welcome response to four years of President Joe Biden’s incompetent and bankrupt progressivism.

Since his electoral victory last November, Governor J.B. Pritzker and Mayor Brandon Johnson have spared Trump no word of condemnation. In a statement one day following Trump vanquishing Vice President Kamala Harris at the ballot box, Pritzker was unrelenting in his criticism of the then-president-elect. In a statement convulsing with cheap shots and alarmism, Pritzker declared:

“Our most vulnerable communities woke up to new uncertainty about their future, scared that their rights will no longer be protected, and unsure whether this nation still stands with them.”

Promising to protect Illinois in a statement resembling a third-rate “Dirty Harry” impersonation, Pritzker said: “You come for my people, you come through me.”

In Chicago, Mayor Johnson behaved little better. In a statement released by City Hall, Johnson postured morally righteous, bemoaned Trump’s return, and promised to protect “vulnerable communities” from the new president’s “hate” and “attacks.” At a later press conference, Johnson preposterously claimed that Trump intended to destroy public education in reaction to the incoming administration's plan to dismantle the Department of Education. Though Trump aims to return authority over education issues that states had historically controlled, Johnson chose to assail Trump as an authoritarian bent on destroying Chicago and pose as the defender of the weak, the powerless, and the vulnerable.

Considering their overwrought reactions to the return of Trump to the Oval Office, it is obvious Pritzker and Johnson view Trump as an asset to their political fortunes. Pritzker, who is positioning himself for a run for the White House and Johnson, who is running for his political life, both believe opposing all things Trump will enhance their political futures. A state and city facing multiple crises — fiscal dislocation, failing schools, and broken transit systems — Pritzker and Johnson might want to rethink their strategy of inciting a public feud with Trump. After all, with the departure of Joe Biden from Washington, D.C., Illinois can no longer rely on $54 billion handouts.

It would be prudent for the Trump Administration to avoid being lured into a public scrap with either Pritzker or Johnson. The new administration would be wise to look beyond Pritzker and Johnson and consider several actions which can help Chicago overcome several crises and lift Democrats’ bootheels off the Windy City.

Public safety consent decree

CWB Chicago reports that since 2020, nearly 400 suspects arrested for murder or attempted murder while on bail or electronic monitoring were awaiting trial for another felony. With police making arrests in only a third of murders and five percent of attempted murder cases since 2020, the number of murders and attempted murders by those released while awaiting trial for other felonies is many times higher. Currently, at least 90 percent of those who have committed the most violent crimes are walking the street. The criminal justice system in Cook County is failing residents.

The criminal justice system is a multifaceted and multibillion-dollar enterprise, and city, county, and state agencies are all involved. Yet only Chicago Police are under a federal consent decree that measures success by the number of police shootings and unfortunately ignores the significant increase in both city violence as well as violence against police officers. It is time for real transparency and an examination essential to holding all the criminal justice system players to account.

It is important for voters to be aware that Cook County Board President Toni Preckwinkle and the ecosystem of lawyers, lawyers, advocates, researchers, consultants, and consent decree monitors who help her stay in power will use all means to fight efforts to bring transparency. Expect Preckwinkle and her allies to gaslight critics or wage a war against anyone who questions or deviates from progressive criminal justice reform measures applied under former State’s Attorney Kim Foxx. For those skeptical of how determined this effort to undermine attempts to stray from the progressive ethos, the election of Cook County State’s Attorney Eileen O’Neill Burke’s serves as a cautionary tale. While campaigning for office Burke was assailed by Preckwinkle and her associates, who engaged in a well-coordinated smear campaign alleging Burke was a MAGA Republican determined to return to the “racist policies and practices” of the past.

If the ISC effort to bring real transparency, and with it, accountability, fails, it may be time to seek a federal consent decree that will force Cook County’s criminal justice system to do its job. This means the Cook County Board, the Sheriff, the States Attorney and the judges. The primary goal of that consent decree should be to keep dangerous and habitual criminals off the street and fully protect both witnesses and victims as well as police and other first responders.

Public education consent decree

The Chicago Public Schools (CPS) does not suffer from a revenue problem but a spending problem. At the very center of CPS’ financial problem is what the district spends its budget dollars on. Unfortunately, school district leaders have long collaborated with the Chicago Teachers Union (CTU) to preserve the status quo. The administration seeks to sustain its resource consuming bureaucracy and maintain control over local school resources. CTU leaders need the central administration to enforce its contract which increases its numbers and members' pay and benefits while limiting accountability and protecting the unions education monopoly.

There is a pathway to address the current financial crisis and dramatically expanding quality school choices. This requires not only tying a contract to available revenues but also by radically decentralizing the school district and allowing the majority of funding to flow directly into local schools. It also requires empowering school principals and their elected Local School Councils (LSCs) to determine how best to spend education dollars. This would include the authority to select the best school model and determine the best uses of the school facility.

It is time for Governor Pritzker to intervene and revive the Chicago School Finance Authority (SFA), similar to the panel established in 1985, which kept the district from financial collapse, to exercise financial control over and furnish financial guidance to the Chicago Board of Education. The goal should not only be to approve budgets and contracts to secure a financial basis for continued operation of the schools but to also strengthen local school autonomy and expand public school choices for all families.

Simultaneously, school reform advocates, who are fighting to keep the CTU from controlling the elected school board, should push for a federal consent decree that will end an education system that sees poor overwhelming minority families in Chicago confined to failing schools by virtue of their income and zip code. The objective would be to ensure that the money follows the students, parents are empowered to select the best school for their child, and local school leaders are empowered to select the best model for their neighborhood.

An independent United States Attorney

It has been decades since the federal government carried out a sweeping investigation into political malfeasance in the Windy City. A city known for its tough urban politics, corruption and incompetence run through Chicago city government like a thread. Long known as a cesspool of corruption, one area in which President Trump can be of great use to Chicago is the appointment of a truly independent U.S. Attorney determined to scrupulously and dispassionately investigate the epidemic of corruption in Chicago.

For starters, a new U.S. Attorney should move swiftly to probe the misuse or fraud involving COVID-19 relief funds. In response to the Coronavirus ravaging the globe, the federal government distributed $53.8 billion in assistance statewide. Of the nearly $54 billion allotted to the state, local governments, universities, mass transit agencies, and health care providers, Chicago accepted $1.9 billion, Chicago Public Schools (CPS) received $2.8 billion, and Chicago Transit Authority (CTA) collected $2.1 billion.

Although the aim of the CARES Act was to impart financial assistance to cover necessary expenses incurred due to the COVID public health emergency, Chicago spent profligately, mainly on expanding government and services. Far from what CARES Act assistance was intended, the reckless misspending of COVID relief has left Chicago in a lurch as the city and CPS are facing budget deficits of $1 billion each for 2025. The CTA is contending with a $567 million deficit, equal to 25 percent of its current budget.

In collaboration with the Justice Department’s COVID-19 Fraud Enforcement Task Force (CFETF), a new U.S. Attorney would best serve Chicago to conduct a thorough probe into how COVID funding was frittered away. As for the justification for this action, it is necessary to consider clear, documented evidence of unemployment benefits fraud, proven instances of Paycheck Protection Program (PPP) involving hundreds of city employees, and an unwillingness to cooperate with the federal government in the enforcement of federal law.

Homelessness

Though President Trump and Mayor Johnson are on opposite ends of the political spectrum, in at least one area — homelessness — Mayor Johnson might be able to come to a mutual understanding with the Trump White House. As he ran for mayor in 2023, the very center of Johnson’s campaign for City Hall was a determination to solve the vexing problem of homelessness.

It is estimated some 18,000 individuals have fallen into the netherworld of homelessness in Chicago, a majority of whom live in tent communities scattered throughout the city. Though from a distance these tent communities appear to be harmless settlements, upon closer examination, the conditions in these tent communities resemble a small scale third-world country. In homeless tent encampments broken lives are everywhere: The filthy and crazed — homeless with knapsacks and blankets — wander aimlessly, stopping here and there to pick through garbage piles, the clutter of drug needles and litter pockmark the landscape, the stink of urine, filth, and fire hazards are found all over.

Although Johnson’s remedy to address homelessness, "Bring Chicago Home," a $100 million ballot initiative, failed at the voting booth, Trump is proposing a different, temporary solution. Under Trump’s proposal, large parcels of land would be set aside for the fabrication of tent cities to relocate and house homeless individuals. Trump’s plan would staff the tent cities with medical and mental health professionals to assess each individual’s condition and offer treatment for the mentally ill and addicted.

Like Johnson, Trump understands being both homeless and mentally ill is a terrible combination.

Trump’s plan includes a national ban on urban camping and directing individuals diagnosed with mental illness to institutions where their conditions can be treated. Although Illinois and Chicago set their own homeless policies, the federal government administers funding and Trump could use federal aid as leverage to persuade Chicago to align with his plan.

Opportunity Zones

Lamentably, too many neighborhoods in Chicago remain blighted by poverty, massive inequality, and scarred by decades of crime. Since arriving in office, Mayor Johnson has been fond of bandying around the term “disinvestment” when describing the South and West Sides of Chicago. While Johnson is correct these neighborhoods have suffered from neglect, the mayor has ignored the role Chicago’s unfriendly tax rates have played in discouraging private investment in economically depressed areas.

Regrettably, Mayor Johnson has shown no indication of reversing Chicago’s unreceptive tax rates to bolster private investment.

To Johnson, the antidote for decades of low capital flowing into poorer communities is to tax heavily and turn the wealthy’s riches into the property of the many. Johnson insists progressive “streams of revenue” — another version of the old “soak the rich” routine — will be an acorn which will sprout into a giant economic oak tree in neighborhoods crippled by poverty.

Unlike Johnson, who is four-square behind big-government programs, President Trump believes in the might of the private investment to revitalize impoverished neighborhoods, create jobs, and drive upward social mobility.

Therefore, with Trump returning to the White House, Chicago can expect a revival of Opportunity Zones. Created in the 2017 Tax Cuts and Jobs Act, Opportunity Zones (OZ) are a federal tax incentive which permits investors with recognized capital gains to deploy capital into projects and businesses located in designated areas in exchange for federal tax advantages. One of the most innovative programs ever created for the purpose of urban renewal, OZs were envisaged with flexibility in mind and its tax incentives can be used for commercial and industrial real estate, housing, infrastructure, and existing or start-up business investments. 

Unlike the traditional tax cut model to lure investment in blighted areas, OZs use capital gains incentives to propel investment. Between its establishment in 2017 and 2020, Opportunity Zones unleashed $48 billion worth of direct equity capital for investing in targeted low-income communities affecting over 30 million residents nationwide.

Trump can reestablish a norma of civility and law-abidingness in Chicago

The Trump White House is both positioned and disposed to come to the aid of Chicago. Trump clearly demonstrated his desire to restore America’s declining urban centers in his first term. The question here is, of course, is Mayor Brandon Johnson amenable to Trump’s willingness to come to the aid of Chicago. Though President Trump has expressed a genuine desire to address the pervasive, trans-generational poverty which plagues Chicago, failing schools, and the contagion of crime overwhelming the city, it is highly unlikely under virtually any circumstance Johnson will cooperate with Trump.

A progressive theologian and incompetent, the only assistance from Washington, D.C., Johnson recognizes comes in the form of massive amounts of federal aid. For Johnson to expect only a generous federal aid package is a terrible but unsurprising error on the mayor’s part, for if Johnson were to work jointly with Trump, the mayor could claim credit for raising living standards and quality of life in Chicago and be commended for setting aside ideological differences for the benefit of residents.

Unfortunately, Brandon Johnson is not a competent mayor and his declining assistance from Trump should be viewed as a missed opportunity. Instead of greeting Trump with open arms, Chicago should expect Mayor Johnson to wage an ideological war on the Trump White House, complete with the mayor’s standard shtick of name calling, vengefulness, sarcasm, and claiming victimhood. Chicago should also be prepared for Johnson to ratchet up the charges of racism against Trump over the next four years.

Trump should avoid taking Johnson’s bait. Trump does not need the aggravation, a distraction, or a public feud with the mayor and Trump can take action in Chicago with or without Johnson’s cooperation. In the absence of any collaboration the mayor, Trump should take steps where he is at liberty to improve Chicago’s schools, clean up corruption, and improve the conditions on Chicago’s crime-ridden streets.

Should Trump make even the slightest difference, the president can then claim a victory and condemn Johnson as an unreliable, inept, and lazy mayor.

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