Breakdown of Chicago Mayor-elect Brandon Johnson's proposed taxes

On the morning after his big victory, Chicago Mayor-elect Brandon Johnson greeted commuters at the CTA’s Chinatown Red Line stop.

"The work that we have to do together ahead is something that I’m looking forward to," he said.

Johnson takes office in five-and-half weeks, when the hard work really begins.

He won the mayor's office despite drawing fire for proposing $800 million in new taxes. He promised the revenue would expand anti-violence programs, mental health services, and other social spending, including a big round of new hiring at Chicago’s public schools.

But even some of Johnson’s City Council allies are skittish of that huge price tag.

"Before we jump into a revenue conversation, the money that we may be looking to do these programs with may already be there if we just do some adjustments," said Ald. Jason Ervin.

Still, Ervin of the West Side’s 28th ward predicts that a majority of the council will eventually approve Johnson's tax agenda. Parts of Johnson’s mammoth tax increase plan, though, also requires approval by the state and even federal governments.

So, one big challenge facing Johnson is how to pay for the new public spending he has promised.

Johnson’s proposals include a new real estate transfer tax and a new tax on aviation fuel at the airports — both need state or federal approval and can't be done by City Hall alone.

"Campaign promises aren't always things that can be kept. When the rubber meets the road, there's a lot of rules in place that prevent you from just doing whatever you want," said Ald. Scott Waguespack.

Also on Johnson’s list of proposed tax increases is to make Chicago’s hotel-motel tax the highest in America. Before the pandemic, the local hospitality and tourism industry was the city's number one private employer, with many minorities among the work force. Millions of pre-pandemic tourists have not returned, nor have thousands of pre-pandemic jobs, a big reason Johnson’s proposed tax increase on hotels could face a fight in the City Council. Not to mention Johnson’s proposed $100 million user fee on North Michigan Avenue and the nearby commercial district.

"You don't want to lose those jobs by putting such a heavy tax on that the restaurants close or the hotels have to restrict the work that they do. So, you don't want to impact those workers as well," Ald. Waguespack said.

The taxpayer watchdog Civic Federation explained all of this in a 92-page report four years ago, as Lori Lightfoot was about to take office. It's still online, where a new mayor-elect can read it anytime he wants.

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Then, there's a possible financial transaction tax that experts say wouldn't general much revenue at all, since the CME Group and others could easily begin to execute trades outside of Chicago, putting them beyond the reach of local tax collectors. Supporters of the idea note that financial trades in London pay such a tax, but that tax is imposed by the national government, making it harder to dodge.

Meanwhile, Illinois Governor JB Pritzker says he looks forward to working with Johnson, who he says he will bring a "new vibrancy to the city."

"I do believe that this is a change for the city. Something new," Pritzker said on Wednesday.

The win in Tuesday night's runoff election is a major victory for the Democratic Party’s progressive wing, as the heavily blue city grapples with high crime and financial challenges.

Outgoing Mayor Lightfoot had some words of advice for Johnson: stay humble and be grateful.

Those words came on Wednesday during an emotional news conference following the fire department's second loss of a firefighter in as many days. Lightfoot was asked what advice she has for Johnson in leading the city through similar tragedies. She described how during her term she regularly reached out to firefighters, police officers, and 9-1-1 call takers and dispatchers to show her support.

"When you've seen what I’ve seen. When you've had to make the calls that I’ve had to make, you better be humble and you better be grateful," Lightfoot said. "It's hard to motivate people when they don't think that their leader has their back, and it's absolutely essential."

Lightfoot says she will share her thoughts directly with the mayor-elect as soon as they have time to meet in-person.