Chicago Mayor Brandon Johnson is intensifying his confrontation with President Donald Trump’s immigration enforcement agenda, signing a new executive order that places additional requirements on companies seeking lucrative contracts with the city.
The sweeping order requires certain contractors to disclose information about their corporate leadership, workplace practices and business relationships with government and law enforcement agencies, including U.S. Immigration and Customs Enforcement (ICE).
Johnson argues the new requirements will give taxpayers greater transparency about companies receiving public money. Critics, however, are raising questions about whether Chicago should use its enormous purchasing power to scrutinize businesses that cooperate with federal immigration authorities.
The Department of Homeland Security has already fired back, making clear that the Trump administration has no intention of backing away from immigration enforcement in Chicago.
The escalating dispute puts two very different approaches to immigration, government spending and law enforcement on a collision course.
Chicago Puts New Requirements On City Contractors
Johnson signed Executive Order 2026-6, officially titled “Establishing Ethical Procurement Standards to Protect Taxpayers and Our Communities.”
The mayor said Chicago should know more about the companies benefiting from taxpayer-funded contracts, including information about the people running those businesses.
Johnson said companies seeking contracts with Chicago should be transparent about whether their leadership reflects the diverse communities whose tax dollars fund city business.
The executive order directs Chicago’s chief procurement officer to establish new rules governing contractors.
Under the plan, vendors found responsible for certain public integrity violations, workplace discrimination or wage theft during the previous five years could be barred from doing business with the city.
Contractors will also face additional disclosure requirements concerning their relationships with other government and law enforcement agencies.
ICE Relationships Could Face Greater Scrutiny
One of the most politically significant provisions concerns companies that work with law enforcement agencies such as ICE.
Contractors must disclose whether they received more than $500,000 from government or law enforcement agencies. Companies must also disclose certain proceedings involving allegations of excessive force, unlawful detention, unconstitutional policing, discrimination or other civil rights violations.
That could expose companies involved in federal immigration enforcement to additional public scrutiny in one of America’s largest Democratic-controlled cities.
There is, however, an important distinction.
Doing business with ICE does not automatically disqualify a company from receiving a Chicago contract.
Instead, the executive order creates disclosure requirements while establishing separate restrictions related to specified integrity, discrimination and wage theft violations.
That distinction matters as the political fight surrounding the order intensifies.
Trump Administration Fires Back At Johnson
The Department of Homeland Security strongly criticized Johnson’s latest action, accusing the Chicago mayor of targeting American companies that cooperate with federal immigration authorities.
A DHS spokesperson accused Johnson of using taxpayer money to advance Chicago’s sanctuary-city policies while resisting enforcement of federal immigration law.
The department then delivered a direct message to City Hall.
The spokesperson stressed that the administration has no plans to back down, saying ICE will continue carrying out federal immigration enforcement in Chicago under President Trump regardless of opposition from city leaders.
The response demonstrates how dramatically immigration policy has divided the Trump administration and Democratic leaders in cities such as Chicago.
Trump has made immigration enforcement a major priority of his administration, while Johnson has repeatedly attempted to limit Chicago’s cooperation with federal immigration operations.
Neither side appears prepared to retreat.
Billions In Taxpayer-Funded Contracts At Stake
The controversy is particularly significant because of the enormous amount of taxpayer money involved in Chicago’s contracting system.
Johnson announced the executive order alongside the “Not With Our Money” campaign, which has urged governments to examine companies involved with federal immigration enforcement.
According to research cited by the campaign, 42 companies holding approximately $3.19 billion in Chicago contracts also conduct business with ICE.
That figure puts billions of dollars in government contracts at the center of the debate.
Johnson’s supporters argue taxpayers should know more about the companies receiving city money and how those businesses operate elsewhere.
Critics may see the policy differently, particularly if businesses cooperating with federal law enforcement face additional political pressure or administrative requirements as a result.
For taxpayers, the bigger issue may be whether the new rules improve accountability or simply add another layer of bureaucracy to Chicago’s already massive procurement system.
Major Companies Face Diversity Reporting Requirements
Immigration enforcement is only part of Johnson’s executive order.
Large private companies whose corporate families report at least $1 billion in net income will also face additional disclosure requirements involving leadership demographics, board composition and diversity policies when they are not already covered by applicable Illinois reporting requirements.
Contractors must additionally provide information concerning efforts to hire and promote formerly incarcerated individuals.
Future companies receiving city contracts will generally be expected to update required disclosures at least annually.
The information will also be made public, creating another layer of scrutiny for companies competing for Chicago taxpayer dollars.
The move comes as the Trump administration takes a different approach at the federal level.
The Equal Employment Opportunity Commission has proposed rescinding certain annual reporting requirements involving aggregate employee race, sex and job-category information.
EEOC Chair Andrea Lucas has argued those requirements raise constitutional concerns and could interfere with the enforcement of federal equal employment laws.
Chicago is now moving in the opposite direction by seeking additional information from companies receiving city business.
Johnson’s Previous Battles With ICE
The latest executive order isn’t Johnson’s first confrontation with federal immigration authorities.
In October 2025, Johnson issued a separate executive order barring ICE from using Chicago-owned parking facilities, empty lots and garages to stage operations, process individuals or conduct civil immigration enforcement activities.
The policy generated criticism from federal officials and became another flashpoint in the broader battle over sanctuary-city policies.
Johnson has continued taking an aggressive stance toward Trump’s immigration policies since then.
Meanwhile, federal authorities have continued immigration enforcement operations in the Chicago area.
DHS previously reported that Operation Midway Blitz resulted in more than 4,500 arrests by December.
The latest contracting order indicates Johnson’s resistance is expanding beyond where federal immigration officers can conduct operations.
Now, the dispute extends to private businesses, government contracts and billions of dollars in taxpayer spending.
Taxpayer Money Becomes The Next Battleground
The political disagreement ultimately centers on a larger question: Should a city use its purchasing power to advance policies that conflict with the federal government’s immigration agenda?
Johnson believes Chicago has every right to demand greater transparency from companies benefiting from public contracts.
His administration argues taxpayer money should support businesses that meet the city’s standards on workplace practices, integrity and corporate responsibility.
The Trump administration has a dramatically different view, particularly when companies cooperating with federal immigration authorities become part of the equation.
For conservatives, the executive order is likely to fuel an already heated national debate over sanctuary cities, federal immigration enforcement and whether Democratic-controlled local governments are creating unnecessary obstacles for ICE.
For businesses, the issue is more practical.
Companies seeking Chicago contracts may now have additional information to disclose, additional compliance requirements to consider and potentially greater public scrutiny surrounding their government relationships.
And for taxpayers, billions of dollars in city contracts make this more than another political disagreement between Trump and a Democratic mayor.
It is also a fight over how government spends public money — and what conditions politicians should be allowed to attach to it.
With Johnson continuing to challenge Trump’s immigration policies and DHS promising that ICE enforcement will continue regardless of City Hall’s objections, the battle between Chicago and Washington appears far from finished.