Bloomberg

Chicago is racing the clock.

Nowhere will political power evaporate more dramatically at noon on Jan. 20 than in the third-largest U.S. city, a bastion of Democratic power that’s enjoyed special access to Washington during President Barack Obama’s eight years in the White House.

When Donald Trump becomes the 45th president, Chicago will trade a first family and top advisers with deep ties to the city for a chief executive who has repeatedly called it a violent mess embodying the failed policies of his predecessor and the Democratic Party.

Mayor Rahm Emanuel is urgently seeking $1.1 billion in federal grants to renovate mass-transit lines. The city and state of Illinois are trying for $110 million in U.S. Department of Transportation grants for grade-crossing improvements to speed trains through the nation’s busiest rail hub. They also want federal financing for improvements to Union Station, a downtown landmark.

Not since the era of Abraham Lincoln have Chicago and Illinois enjoyed such strong ties to the White House and Washington. Obama’s exit will bring an end to that, as he leaves along with fellow Chicagoans including Commerce Secretary Penny Pritzker and senior White House adviser Valerie Jarrett.

“A state does have a home-town advantage through longtime friendships, greater access and more attentive and sympathetic ears when one of its own sits in the Oval Office," said Karen Hughes, an adviser to former President George W. Bush. "Illinois’s elected officials may now find themselves on the outside and opposite side of many policy debates with the new administration, much as Texas elected officials did during the years of President Obama’s administration.”

In the Loop

In some ways, Chicago already has been easing into the post-Obama era. When the former junior senator from Illinois moved into the White House in 2009, many of the administration’s top jobs were held by Chicagoans, including Emanuel as chief of staff, Arne Duncan as education secretary, Desiree Rogers as social secretary and David Axelrod as senior adviser.

“It changes the game,” said Dick Durbin, the senior senator from Illinois and an Obama confidant. “We didn’t have to explain to the Obama administration where they could find Chicago or Illinois. They knew. And when we talked about issues back home, here, there was usually somebody in each Cabinet department who was from Illinois and could help us.”

For Trump, Chicago has often been a weapon for attacks against Obama and Democratic policies. During the campaign, he questioned the city’s policing and said he could in “one week” stop its violent crime -- Chicago recently recorded its 700th homicide of the year.

Chicago also is the one U.S. city where Trump canceled a 2016 campaign event because of unrest. In March, he abruptly called off a rally near downtown at the University of Illinois campus, setting off a melee of shoving and taunting between supporters and opponents inside an arena. Trump said the situation violated his rights to free speech, while opponents blamed him for fomenting the confrontation.

Heightening tensions, the city council voted a week before the election to remove an honorary street sign designating “Trump Plaza” near the 96-story Trump International Hotel & Tower, a building that bears his name in large, white letters.

Chicago has long been a punching bag for Republicans looking to criticize Obama. In the 2008 presidential campaign, Senator John McCain of Arizona ran a national television ad that attacked him as “born of the corrupt Chicago political machine.”

Emanuel has said he’s not worried about Chicago getting shut out during Trump’s tenure. He has some standing with the billionaire businessman, who donated $50,000 to Emanuel in 2010 when he was first running for mayor. After Trump’s election victory, the president-elect called Emanuel to pick his brain on transition matters, Politico reported.

The mayor has one other point of access to the president-elect: Ari Emanuel, his younger brother, has acted as Trump’s entertainment agent.

The incoming president won’t have a lot of reasons to look kindly on Illinois. He won just 39.4 percent of the state’s vote, his eighth-lowest percentage, according to unofficial election returns.

Going Begging

The state’s lost power comes as Illinois faces a budget standoff and fiscal crisis that have triggered dismissals at universities, left $9 billion in unpaid bills and cut into services for the poor. Investors are demanding yields about 2.2 percentage points higher for 10-year Illinois debt compared with benchmark securities.

Representative Dan Lipinski, a Democrat who serves on the U.S. House Transportation and Infrastructure Committee and represents a moderate district on Chicago’s southwest side, said he’s keeping an open mind when it comes to dealing with the new president.

“I would assume we won’t be as well off under the Trump administration,” he said, “but I’m not going to count us out yet.”

The project Illinois is most urgently seeking is the one involving two elevated mass-transit lines. The so-called “core capacity” money, a program created at Durbin’s urging, is pending before the U.S. Department of Transportation. Speaking to reporters last week, Emanuel expressed confidence in securing the $1.1 billion. 

“Literally, in Washington, there’s a check with Chicago’s name on it,” he said. “Over 50 percent of the resources are going to come from Washington, and I don’t want to miss an opportunity.”