A mass deportation that transforms a sanctuary city that has spent more than $440 million to welcome migrants.A federal spigot that runs dry before completing the $5.3 billion extension of the CTA Red Line to 130th Street.An O’Hare Airport expansion project — already revised to rein in $1.5 billion in cost overruns — that grinds to a halt before a global terminal and two satellite concourses get built.Mayor Brandon Johnson’s administration has good reason to be on edge one day after former President Donald Trump overcame multiple indictments and a conviction, a pair of assassination attempts and the withdrawal of an incumbent Democratic president to pull off the biggest political comeback in modern American history."There's a couple of fears. One is implementing a plutocracy, upward re-distribution, governing on behalf of billionaires and not for everyday working people, which is what the mayor's vision is based on," senior mayoral adviser Jason Lee told the Sun-Times Wednesday."The other fear, obviously, is the authoritarian impulses. The enemy within. Going after political dissidents. Curtailing freedom of speech, freedom of movement. Curtailing rights as it pertains to women."Chicago was a political pincushion for Trump during his first term as president. The city is likely to be an even bigger target during a second Trump presidency if the GOP controls both houses of Congress.Chicago a frequent punching bag for TrumpThe city Trump has long condemned as a crime-infested cesspool could be in line for political payback. A notoriously vindictive Trump may be itching to get even with Mayor Brandon Johnson, who campaigned for Vice President Kamala Harris and hosted her coronation at the Democratic National Convention.Johnson was simply doing “what most prominent Democratic politicians, including governors” have been doing by “making the case for their candidate," Lee argued.“All we can do at this point is take the President-elect at his word that it’s time to unify the country and hope that he wants to be a president for all of America, including Chicago. … We have powerful allies in Washington and allies in other cities. And we’ll work together to make sure cities like Chicago continue to get the resources they’ll deserve.” Looking south from 95th Street at the end of the Red Line. The city is about to begin construction of an extension of the Red Line to 130th Street, but has not yet secured all the federal funds it needs, and that money could be at risk in a second Trump administration.Sun-Times file Will Red Line extension be derailed?One of the Johnson administration’s biggest fears involves the 50-year-old dream of extending the Red Line south to 130th Street from its current terminus at 95th Street.Earlier this year, U.S. Rep. Mike Quigley and his fellow Illinois Democrats persuaded the Biden administration to speed up federal funding for that project. Instead of receiving $350 million for the 5.6-mile extension during the first year of the full-funding agreement, the CTA will get $746 million, saving the city $213 million in financing costs.The CTA Board has since awarded a $2.9 billion contract in hopes of starting construction later this year or early next year — but only if the project clears another major hurdle.“We expect to sign a full-funding grant agreement with the [Federal Transit administration] and do so at the end of this year or early next year,” said CTA spokesperson Catherine Hosinski.In 2016, then-Mayor Rahm Emanuel moved heaven and earth to nail down $1.1 billion in federal grants to modernize the CTA's Red Line before then-President Barack Obama left the White House. Emanuel convinced the City Council to authorize a transit tax increment financing district to provide the local matching funds that once would have been provided by a state capital bill and signed the ordinance on the final day for the city to demonstrate its commitment.Hosinski was asked if the CTA would nail down that full-funding agreement before President Joe Biden leaves office.“I don’t know if it’s necessary to race. Our timeline already aligns with that,” she said.Quigley could not be reached for comment.Lee said he expects the full-funding agreement to be “wrapped up prior to” Trump’s second inauguration."We'll have to be vigilant" about a new Trump administration trying "to claw something back," Lee said, but he added: “This is a major infrastructure project. You would hope that he would see the value of that and focus on other issues.” Efforts to expand and modernize O’Hare International Airport will require federal funds.Associated Press O’Hare expansion could hit turbulenceYet another big-ticket item is the long-stalled O’Hare modernization.To cut costs and appease the two major airlines footing much of the bill, Johnson proposed a major change in the order of construction.The new agreement will allow the city to build a 19-gate satellite concourse first, before the "global terminal" that would replace what is now Terminal 2. A second satellite concourse, with a connecting tunnel, would be completed only if sufficient funds remain after other work is finished.The city will provide regular cost estimates, and also will need approval from United and American before either cutting the scope of the project or spending more than $6.1 billion.Johnson has refused to even entertain the possibility of running out of money before the second satellite concourse gets built — but Trump may leave the mayor little choice.“O’Hare is significant to American competitiveness. It’s one of the nation’s most important airports," Lee said. Trump "has been an advocate for both infrastructure and for things that enhance America’s global position. You would hope that he would see this expansion in keeping with some of the values that he professes." Mayor Brandon Johnson meeting migrants staying at the 12th Police District station, 1412 S. Blue Island Ave., in May 2023.Anthony Vazquez/Sun-Times file Mass deportations ‘self-defeating’Johnson also wants more federal funding for policing and violence intervention, as well as for a migrant crisis that already has cost Chicago taxpayers more than $440 million and could get worse.Still, noting the city's recent move to a “unified” shelter system for both asylum seekers and the unhoused, Lee said that "flows into the country have been significantly reduced over the tail end of the Biden administration. We’ll stay vigilant on advocating for whatever resources are available."As for threatened mass deportation, Lee said he can only hope it’s more rhetoric than real.“A mass deportation without due process would seem to be self-defeating for someone who wants to bring down costs for the average American,” Lee said.“It would have significant negative moral and ethical impact but also significant negative economic impact on not just Chicago, but on the entire country. It would contribute to rising costs.”