Former mayor Lori Lightfoot knows well what a second Donald Trump administration would look like for Chicago. After all, she had to deal with the former president during his term in the White House. “Trump devalued cities,” she says. “He didn’t provide us with resources, but he constantly held us up for derision and used us as a punching bag.” As you might recall, Trump compared Chicago to a Middle Eastern war zone, carped that its crime rate was “an embarrassment to the nation,” and called the police superintendent “a disgrace” for protecting undocumented immigrants.

When Lightfoot was mayor, her top priority with the federal government was legislation to stop gun trafficking. Trump, she says, “had no appetite for that.” Lightfoot also wanted funding for big infrastructure and transportation projects, including a Red Line extension, but “there was no opportunity for any.” What federal aid the city did receive was unwanted: Operation Legend brought in agents from various law enforcement groups to assist the police in cracking down on a crime surge. Lightfoot dismisses the operation as a publicity stunt, disputing the Justice Department’s claim that it contributed to a 50 percent drop in homicides.

After the 2020 election, President-elect Joe Biden’s team reached out to Lightfoot. “I became so overwhelmed that someone was asking my opinion, I almost broke down in tears,” she says. Under Biden, Congress passed a gun violence bill, and the feds committed $746 million to extend the Red Line south to 130th Street. Lightfoot worries that money could disappear if Trump gets elected: “Of course we’re nervous about that. I think local government and big cities would be big losers under Trump, because I don’t think he understands the importance of our role in the economy, our role in democracy.”

Much of his barrage would likely stem from his No. 1 issue: immigration. Last time around, he tried to cut federal funding to Chicago and other “sanctuary cities” that refused to cooperate with his deportation efforts. That move was thwarted by the courts. But he’s doubling down on what he promises will be the largest deportation program in U.S. history.

Luis Gutiérrez, CEO of the Little Village immigrant support group Latinos Progresando, says his community is already preparing by holding legal-rights seminars and by identifying churches and schools to serve as sanctuaries for immigrants in the event of Immigration and Customs Enforcement raids. “When it comes to a new Trump administration, there’s a lot of fear in the city of him building on what happened the last time he was in office,” Gutiérrez says. “He’s learned a lot. In a second term he’s going to be more determined to do the things he was talking about in his first term. We have to brace ourselves.”

If Trump makes good on his vow to seal the borders and deport migrants with criminal records, that would aid Chicago in one sense: It would reduce the strain the city has felt in trying to accommodate busload after busload of newcomers. That flow has already eased some of late, after Biden implemented restrictions on asylum seekers.

At Trump’s insistence, the Republicans’ campaign platform says decisions on abortion should be left up to the states. What would that mean for Chicago? The city, along with the rest of Illinois, would remain a destination for women seeking the procedure. Planned Parenthood recently opened a Waukegan clinic, to cater to patients from Wisconsin, and a Flossmoor clinic that draws from Indiana.

But Jennifer Welch, executive director of Planned Parenthood of Illinois, doesn’t believe that Trump will stay hands off: “Ending Roe v. Wade was just a warm-up lap.” Among the fears: A Trump-appointed judge could block access to the abortion pill mifepristone. Or a Trump-appointed Food and Drug Administration director could curb use of the morning-after pill. Such changes could force even more pregnant women into what Project 2025, a conservative blueprint for a Trump Administration, dubs “abortion tourism,” making Chicago and Illinois possible targets for federal retaliation.

As for environmental issues, Trump’s administration would be a less-than-vigilant guardian. That might be a plus for industry, and even some city officials, but a threat to residents. During Trump’s presidency, oil refineries in Indiana were “dumping chemicals into Lake Michigan while the Environmental Protection Agency was basically asleep at the switch,” says Jonathan Sack, the Midwest government affairs director for the Natural Resources Defense Council.

Contrast that with the efforts under the Biden administration. After General Iron moved its metal-shredding business to the Southeast Side, a Department of Housing and Urban Development investigation found that the city tended to steer pollutants to poor neighborhoods. HUD threatened to withhold federal funding if the practice continued. “Can you imagine a Trump Housing and Urban Development Department filing a civil rights complaint on behalf of the Southeast Side of Chicago?” Sack asks. “It’s inconceivable.”

One local who would welcome another Trump presidency is Chuck Hernandez, a retired police detective who chairs the Chicago Republican Party. He expects Trump would commit more federal resources to clamping down on crime here. “When I was interviewing convicted felons at [the police station at] Harrison and Kedzie, just that threat of possible federal prosecutions, where you serve 85 percent of your sentence and you aren’t doing your time here in Illinois, changed their demeanor very fast,” Hernandez says.

He also expects that a U.S. attorney appointed by Trump would be more aggressive than a Democratic appointee in rooting out local corruption But Hernandez is a clear exception. Most of Chicago looks back on Trump’s first term with a sense of weariness and ahead to the prospect of a second term with dread.

Given his penchant for progressive rhetoric, Mayor Brandon Johnson would likely give as good as Chicago gets from Trump. But Manuel Pérez, who as Lightfoot’s deputy mayor of intergovernmental relations dealt with the Trump administration (the closest he got to Donald was a White House meeting with Ivanka), has this advice: Focus on building relationships with the civil servants who will outlast the administration. Also, ignore the barbs. “The less we engage with that and the more we focus on the substance, the more we’ll get out of it.”