On October 24, 2025, a livestreamed conversation hosted by City Club Chicago brought together Democracy Forward President Skye Perryman and Illinois Governor J.B. Pritzker to discuss what they described as an alarming new chapter in American democracy. Their central message was stark: the Trump administration’s recent actions have set disturbing precedents, threatening constitutional freedoms and reshaping the boundaries of government power in the United States.
Perryman didn’t mince words as she described the environment since Donald Trump’s return to office in January 2025. According to City Club Chicago, she argued, “There were certain policies that could be politicized or things that people disagreed on, but the right to stand up and say what you think was not something that presidents and members of Congress that were allied with the president tried to come after.” She drew a clear distinction between the usual push-and-pull of American politics and what she called “persistent and widespread attacks” on democracy itself.
Among the most controversial of these actions was the administration’s deployment of National Guard and military forces to quell protests against immigration policies in cities like Los Angeles, Memphis, and Washington, D.C. As reported by Democracy Forward, court orders have at least temporarily halted similar deployments to Chicago and Portland, Oregon. Yet, the mere threat of military presence has left many residents and officials uneasy. The Seventh Circuit U.S. Court of Appeals, in blocking the deployment to Chicago, pointedly stated, “political opposition is not rebellion.”
The legal battles don’t end there. The administration’s approach to immigration enforcement has drawn fierce criticism, particularly the granting of broad powers to Immigration and Customs Enforcement (ICE) agents. On October 3, 2025, Chicago Alderwoman Jessie Fuentes was detained by ICE agents after she questioned whether they had the judicial warrant required to arrest someone in a hospital—a move Governor Pritzker called emblematic of a wider erosion of rights. “All of us are seeing that rights are being taken away,” Pritzker said, adding, “The First, Fourth, Fifth and Tenth amendments are the ones that are actually under attack by this administration, and I’ve never seen this before in my entire life.”
Those amendments, of course, guarantee fundamental freedoms: speech, assembly, protection from unreasonable search and seizure, due process, and limits on federal power. According to Pritzker, the Trump administration’s tactics are not just policy disputes, but direct assaults on the American constitutional framework. “And it is going on because the Congress is unwilling to do anything now because they are all lackeys for the president,” he charged.
Perryman echoed these concerns, arguing that the administration’s use of military force and ICE raids is designed to normalize a sense of occupation and intimidation. “The abuse of ICE is another place where the president is trying to normalize terror and fear and intimidation,” Perryman said. “It is unconscionable. It shocks the conscience of people across this country, regardless of what their views are about particular immigration policies.” She highlighted the administration’s authorization of ICE raids in hospitals, schools, and churches—a step so controversial that Democracy Forward has filed multiple lawsuits to challenge it.
These legal challenges are not abstract. Plaintiffs include the Alliance of Baptists, Quaker, and Evangelical Lutheran Church in America jurisdictions, as well as the Cooperative Baptist Fellowship, Sikh, and Quaker communities. In several cases, courts have sided with the plaintiffs, issuing orders to block ICE raids in their congregations and houses of worship. The underlying concern, Perryman said, is that law enforcement activity is “preventing not just people targeted by ICE, but everyone who wants to exist in communal worship from being able to do so.”
Governor Pritzker praised Chicagoans for their active resistance—blowing whistles, recording ICE agents during arrests, and mobilizing to protect their neighbors. “They don’t want their neighbors taken away and disappeared, so this city has activated like I have never seen it before. I’m so proud of the people here and we need that to happen all across the country — and it is happening,” he said. Yet, as Democracy Forward noted, Pritzker did not address the actions of his own State Police in confronting clergy and peaceful protesters in Chicago, a detail that adds complexity to the local response.
With Congress largely gridlocked, both Perryman and Pritzker agreed that the courts have become the last reliable check on executive power. Recent decisions by the Ninth Circuit and Seventh Circuit Courts of Appeals have provided some relief by halting military deployments to Portland and Chicago. However, the administration has responded by sending large numbers of ICE and Customs and Border Protection officers to Chicago, a move many see as an attempt to intimidate protesters and stifle dissent against federal immigration policies.
In the midst of these constitutional battles, another controversy has emerged: the Trump administration’s approach to disaster relief. Just days after the City Club Chicago event, on October 28, 2025, Chicago and the state of Illinois announced they were appealing the administration’s denial of a disaster declaration following severe summer flooding. As reported by local news outlets, the flooding caused widespread damage and power outages across the region. Illinois was one of three Democrat-leaning states denied federal disaster aid for flooding, while several Republican-leaning states received approval for their requests.
Governor Pritzker’s administration is now conducting additional damage assessments at residents’ homes, hoping to bolster their case for federal assistance. The timing and political pattern of the disaster aid denials have raised eyebrows throughout Illinois and beyond, with critics suggesting that the administration’s actions reflect a broader pattern of politicization and selective enforcement.
Perryman, for her part, sees a silver lining in the growing wave of civic engagement and legal resistance. “In this moment with this great overreach, what we are seeing in our work is people who might not be on the same side on a lot of issues actually finding common cause. We’re representing people in cases where we have businesses and unions and folks that used to fight with each other, all pushing back on the same thing,” she said. “There is an opportunity in this moment for the people to take back what it means to be in a democracy, to rebuild that democracy because this highly politicized, highly partisan, very far-right activity that we are seeing doesn’t represent the vast majority of people in this country.”
While the nation grapples with the implications of these unprecedented moves, the battle lines are drawn not just in the courts and the streets, but in the hearts and minds of Americans. The coming months will test the resilience of democratic institutions and the capacity of ordinary citizens to defend the freedoms they hold dear.
