Jason Lee, Chicago's shadow mayor, helps Brandon Johnson weather the political storm

As the man widely viewed as Chicago’s shadow mayor, Jason Lee has his hands full these days.

His boss, Mayor Brandon Johnson, barely got his 2025 budget through a frustrated and emboldened City Council after an excruciating process made worse by the rookie mayor’s own mistakes.

The budget bungling ended a disastrous year for Johnson that included self-inflicted wounds involving staff, the defeat of his signature “Bring Chicago Home” referendum and a clumsy and protracted struggle to oust Chicago Public Schools CEO Pedro Martinez after the mass resignation of Johnson’s own appointed school board.

In the meantime, Lee is battling another flare-up of a chronic condition — Crohn’s disease — while defending his decision to cast his November presidential election vote in Texas even though he lives in Chicago. That decision honored a pledge to his late mother, U.S. Rep. Sheila Jackson Lee, to cast his vote in Texas for his sister, Erica Lee Carter, who was running for the vacant congressional seat created by the death of Jackson Lee.

“I’ve been living with it for a while — before I even came in. It’s just a matter of trying to manage it as best I can, which I’ve been doing,” Lee said of the condition. “I wouldn’t say that I’m unable to do that with this job. I’ve just got to stay diligent on my regime.”

Lee said he’s not at all surprised by the extraordinary pressure that both he and Johnson have been under in the shark tank otherwise known as Chicago politics.

He noted that then-Mayor Rahm Emanuel “had thousands of people in the streets asking for him to resign and looking to see if they could do a recall” in the furor that followed the court-ordered release of the video showing the police shooting of 17-year-old Laquan McDonald in 2014.

“This is Chicago. All eyes are on the fifth-floor," Lee said. "If you sign up to participate in that, there’s going to be people who don’t want you to be in the position you’re in and who will work diligently in every way they can to prevent you from either getting there or staying there.”

Lee stressed that he is in Chicago “by choice.” He knows there is “not a long shelf life for people in the highest echelons” of city government.

“It’s not something where, if I don’t do this my life is over or I’m going to go into a deep depression. I do it because I believe in this mayor,” Lee said. “I’ll do it as long as I feel like I can add value to him and the city. If that becomes no longer the case, I’ll move on with no malice or hard feelings.”

Brandon Terry, a professor of social sciences at Harvard whom Lee describes as his “mentor,” said he has spent “a lot of time with a lot of smart people.

"Jason Lee is among the smartest. He’s probably a genius,” Terry said.

Lee’s path to City Hall

Lee followed a winding road toward becoming Johnson’s right-hand man.

The son of a civil rights champion, Lee went from Eagle Scout to Morehouse College to Harvard and back, the second time for a rare trifecta masters degree in religion, ethics and politics.

In between degrees, Lee spent two years as a Wall Street investment banker before moving on to an energy company based in Africa.

It was only then that he became convinced that the labor movement, community organizing and politics held the key to lifting up poor and working-class African Americans.

At a time when the Chicago Teachers Union was making international headlines for its marathon strike against Emanuel, Lee chose Chicago as his laboratory for social change.

It was Johnson who agreed to put suspicions aside and give the former Wall Street banker with a political pedigree a chance to learn the organizing skills needed to build political power from the ground up.

“Brandon Johnson called me. He said, `Someone put your resume in my hand. You should come to Chicago. I’ll train you,’ “ Lee said, recalling his first conversation with the man he would ultimately help to become the 45th mayor of Chicago.

“He and I were immediately on the same wavelength. At the time, I was studying a lot of Martin Luther King and other Black liberation theologians. He put it in that frame. He said, `We’re building a movement. You should come to Chicago. It’s like Selma.’ “

Lee bounced back and forth between Washington and Chicago while working for AFSCME International in Washington.

He then reconnected with Johnson while organizing in the mayor’s home neighborhood of Austin. That flowed into Johnson’s 2018 campaign for Cook County commissioner, followed by a stint as political director for the CTU-funded and affiliated United Working Families.

In 2019, he served as deputy campaign manager for the mayoral campaign of Cook County Board President Toni Preckwinkle.

A setback, the Preckwinkle mayoral campaign

Preckwinkle lost the runoff in a landslide to Lori Lightfoot in a campaign dominated by the federal corruption scandal swirling around now-convicted Ald. Edward Burke (14th). For Lee, it was a “significant learning experience” that would come in handy four years later.

“It was a cataclysmic sea change in Chicago political history when the [first] Burke indictment was unsealed. All four [leading] candidates were significantly negatively impacted by their close proximity to Burke. Those were significant headwinds for our campaign,” he said.

“It was a tough one. For me, it was good. I got to learn the mechanics of a Chicago mayoral race and the dynamics I needed to account for along with the media headwinds. Things can snowball. The infrastructure in a campaign organization can be difficult and expensive to manage. But I got a chance to understand the citywide math.”

Terry said he has “pestered” Lee “a million times” about becoming a candidate for political office himself some day.

“He’d be fantastic. He’s what we need. But it’s hard to convince him to do it. He knows better than anybody the cost of it on family. He was always close to his mom. But, you could tell there’s parts of that life that were really hard on him," Terry said.

Dr. Elwyn Lee acknowledged that his wife’s frequent absences took its toll on Jason and his sister, Erica Lee Carter.

“It’s always hard on kids when their mother is not around as much as other mothers. I was a great dad, but they still missed their mother,” Elwyn Lee said. “But when he grew to understand what she was doing and why she did it, he grew to look at that a little differently because he understood what the sacrifice was for. He was interacting with people for whom she did so much. He realized how valuable that was.”

A family crisis

When Sheila Jackson Lee was diagnosed with pancreatic cancer and given just a few months to live, it was Jason Lee who convinced his mother to be more specific about the announcement of her medical condition and prognosis. He wrote the heartfelt letter that went out in her name to her Houston constituents, Dr. Elwyn Lee said.

“There was weight loss. You could tell she was weak and frail and having mobility issues. It was clear something was going on. But my wife was a very secretive person. She didn’t want people to know she was ill,” the elder Lee, vice president of the University of Houston, told the Sun-Times.

“Jason was very firm in his belief that you need to be more specific than she wanted to be. He knew that if you put something out there just general and ask for privacy given your status, people will be crawling around trying to find out and that wouldn’t be good. By being specific and just by naming the cancer, it gave people the ability to reach out to her."

In July, President Joe Biden was among those in attendance. Vice-President Kamala Harris delivered the eulogy, hailing Jackson Lee as a “social justice warrior.”

Jason Lee choreographed the funeral and summoned the courage to deliver a tribute to his mom that still brings his father to tears.

“He was the one who was in the room when she passed. And he talked about how, in her last moments, she wanted to know had she been a good mother,” the elder Lee said, his voice breaking.

“He said, `Yes, mom. You were a good mother.’ With that mental toughness, he managed to do that without crying. But he made everybody else cry.”

Erica Lee Carter is serving out the remainder of her mother’s term in Congress. She is certain that her younger brother — who volunteered to tutor classmates in economics during high school and helped build a sandbox for a local church as an Eagle Scout — will make a difference no matter where he goes from here.

“His compassion to make progress and change," Lee Carter said, "that’s what drives him.”