Tom Homan has crisscrossed America since President-elect Donald Trump named the former cop and immigration official his border czar, promising “shock and awe” alongside the biggest deportation the U.S. has ever seen.

But wherever Homan goes, from New York City to Texas, he’s zeroed in on two cities he plans to target in the first days of Trump’s new presidency: San Diego and Chicago.

Both places have reason to be high on the priority list for the incoming administration. The San Diego region has emerged as one of the busiest illegal border crossing spots along the Mexican border. Chicago — a perennial punching bag for Trump and a sanctuary city since 1985 — has housed tens of thousands of migrants bused and flown in by Texas Gov. Greg Abbott.

What San Diego and Chicago also have in common are leaders who have vowed to defy Homan by protecting undocumented migrants from deportation. The San Diego County Board of Supervisors voted last month to become what one member called a “super sanctuary” community. In Chicago, Mayor Brandon Johnson has been reiterating in recent weeks that local law enforcement is prohibited from cooperating with federal immigration officials.

“San Diego better get the hell out of the way. We’re coming,” Homan, told a Republican group this month in Texas. “The Chicago mayor,” Homan continued, “said I am not welcome in Chicago. Well, guess where I am going to be on a day one?”

Trump’s team is planning a big immigration raid in the city starting Tuesday and continuing all week, the Wall Street Journal reported, citing people familiar with the planning.

Trump said Saturday that the mass deportations would “begin very early, very quickly.” In an exclusive phone interview with NBC’s Kristen Welker, Trump declined to name the cities in which the raids would occur “because things are evolving.”

While experts questioned whether the plans — dubbed Operation Safeguard, according to the New York Times — would differ dramatically from previous major actions by U.S. Immigration and Customs Enforcement, the signaling right after Trump’s inauguration would be unmistakable.

The Chicago-based National Immigrant Justice Center is advising migrants to consult with an immigration attorney, memorize family phone numbers, establish an emergency contact with their children’s schools and keep all necessary documentation in a secure place.

U.S. Rep. Chuy Garcia, an Illinois Democrat, is working with churches and community groups to help immigrants understand their rights if ICE agents come calling.

“There are good reasons to expect that Chicago would be the primary target,” Garcia said. “We can expect ICE, under new leadership starting on Monday, to be targeting high visibility locations, whether it’s factories or possibly larger restaurants.”

While a flurry of executive orders on immigration and the border is expected when Trump takes office Monday, logistical details of the deportation operations have remained shrouded. Homan has signaled he’ll initially focus on deporting violent criminals, a view largely shared by Democratic leaders such as Illinois Gov. JB Pritzker.

But Pritzker warned of the negative impact, including on the economy, of Homan’s gung-ho attitude.

“He seems like a blowhard to me, and I know that he’s going to go do things that really do affect people’s lives in a terribly negative way,” Pritzker said in an interview Jan. 14. “He thinks that he’s carrying out something that’s good for the country. But it’s not.”

Trump has threatened to withhold federal funding unless cities and states comply with the administration’s wishes. In Chicago, Mayor Johnson has fired back by vowing to defend his city’s immigrant community.

“I promise you we will not bend or break,” Johnson said after the November election. “Our values will remain strong and firm.”

Other cities are dealing with similar challenges while taking different approaches to the change of administration. New York Mayor Eric Adams, who was indicted on federal corruption charges in September, met with Trump on Friday as an adviser emphasized City Hall’s willingness to work with the new president.

In San Diego, by contrast, the board of supervisors last month approved a policy to bar county agencies from working with federal immigration authorities trying to carry about mass deportations.

“We should be deporting felons, not farm workers,” said Terra Lawson-Remer, one of three Democrats who voted for the measure. “We are very concerned about the specter of mass deportations that will make our communities fundamentally less safe.”

Jim Desmond, a Republican supervisor in San Diego County and the lone dissenter in the vote on the super sanctuary proposal, predicted the measure would have little impact. The county sheriff, Kelly Martinez, downplayed the new policies and said her office will continue to follow California state law.

California Attorney General Rob Bonta underlined that state law already limits when and how local authorities can work with federal immigration agents.

“Here in California we are not going to spend our time, money and resources going backward,” Bonta said at a briefing Friday. “You can be sure that as California’s attorney general, if Trump attacks the rights of our immigrants I will be there. If Trump breaks the law, we will see him in court and hold him accountable.”

It remains to be seen exactly how the threats from Homan and vows of protection from local authorities will play out in the coming weeks and months. It’s also unclear which groups of immigrants the new administration will prioritize for deportation. And federal officials face limits in staffing, money and temporary detention space.

But cities are girding for a showdown amid the uncertainty of how Trump’s crackdown will play out. Restaurants from Texas to Colorado are grappling with the uncertainty around potential deportations.

In Denver, Mayor Mike Johnston has said he’s willing to go to jail in order protect migrants in his community. Homan said he’s willing to put him there if Johnston blocks ICE agents from doing their jobs.

“Look, me and the Denver mayor, we agree on one thing — he’s willing to go to jail, I’m willing to put him in jail because there’s a statute,” Homan said in an interview with Fox News in late November. “And what it says is it’s a felony if you knowingly harbor and conceal an illegal alien from immigration authorities. It’s also a felony to impede a federal law enforcement officer.”

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(With assistance from Miranda Davis, Daniela Sirtori and Kate Seaman.)

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