As the man widely viewed as Chicago's shadow mayor, Jason Lee is busy these days.
His boss, Mayor Brandon Johnson, barely got his 2025 budget through a frustrated and defiant City Council after an agonizing process made worse by the rookie mayor's missteps.
The budget fumble capped a disastrous year for Johnson, which included self-inflicted wounds on staff, the defeat of his signature “Bring Chicago Home” referendum, and the clumsy and protracted struggle to oust Chicago Public Schools CEO Pedro Martinez after Johnson’s boss resigned en masse. Special appointed school board.
Meanwhile, Lee is battling another bout of a chronic illness — Crohn's disease — while defending his decision to cast a ballot in November's presidential election in Texas even though he lives in Chicago. This decision fulfilled a pledge he made to his late mother, U.S. Rep. Sheila Jackson Lee, to cast his ballot in Texas for his sister Erica Lee Carter, who was running for the vacant congressional seat left by Jackson Lee's death.
“I've been living with it for a while – even before I came along,” he told me of the condition. “It's just a matter of trying to manage it as best I can, which is what I've been doing.” “I'm not going to say I can't do it with this job. I just have to stay diligent with my regimen.”
Lee says he was not at all surprised by the extraordinary pressures he and Johnson were under in the shark tank known as Chicago politics.
He noted that then-Mayor Rahm Emanuel had “thousands of people take to the streets calling for him to resign and looking to see if they could impeach” amid the uproar that followed a court order for a video showing police shooting 17 people. Year-old Laquan McDonald in 2014.
“This is Chicago. All eyes are on the fifth floor,” he told me. “If you sign up to participate in this, there will be people who don’t want you to be in the position you are in and they will work hard in every way possible to prevent you from getting there or staying there.” .
He assures me that he is in Chicago “by choice.” He knows that “there's not a long shelf life for people at the highest levels” of city government.
Senior Counsel Jason Lee, right, with Mayor Brandon Johnson at McCormick Place in July.
“It's not something, 'If I don't do this my life will be over, or I'll go into a deep depression.' He told me, 'I'm doing it because I believe in this mayor.' “I'll do it as long as I feel I can add value to him and the city. If this is no longer the case, I will move forward without any hatred or negative feelings.
Brandon Terry, a professor of social sciences at Harvard, who Lee describes as his “mentor,” says he 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 way to City Hall
Lee followed a winding path to becoming Johnson's right-hand man.
The son of a civil rights hero, Lee went from Eagle Scout to Morehouse College to Harvard and back, a second time, to earn a rare triple master's degree — in religion, ethics and politics.
Between degrees, Lee spent two years as an investment banker on Wall Street before moving to an energy company based in Africa.
Only then did he become convinced that the labor movement, community organizing, and politics were essential to the upliftment of 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 a laboratory for social change.
It was Johnson who agreed to put doubts aside and give the former Wall Street banker with political pedigree a chance to learn the organizational 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’m going to train you,’” he said, recalling his first conversation with the man who would eventually help him become Chicago’s 45th mayor.
“He and I were on the same wavelength immediately,” he told me. “At the time, I was studying a lot of the work of Martin Luther King and other black liberation theologians. He put it in this context. “We are building a movement,” he said. You should come to Chicago. “She is like Salma.”
Lee moved 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 Austin neighborhood. That flowed into Johnson's 2018 campaign for Cook County commissioner, followed by his stint as political director for the CTU-funded and affiliated United Working Families.
In 2019, he served as deputy campaign manager for Cook County Board Chairman Toni Preckwinkle.
Preckwinkle campaign 'an important learning experience'
Preckwinkle lost the runoff in a landslide to Lori Lightfoot in a campaign dominated by the federal corruption scandal revolving around the now-indicted 14th Ward. Edward Burke. For Lee, this was an “important learning experience” that would come in handy four years later.
It was a catastrophic change in Chicago's political history when the (first) indictment of Burke was unveiled. All four (leading) candidates were significantly negatively affected by their proximity to Burke. “That was a big headwind to our campaign,” he said.
It was tough. For me, it was good. I learned the mechanics of the Chicago mayoral race and the dynamics I needed to consider along with media headwinds. Things could snowball. “Managing campaign infrastructure can be difficult and expensive, but I had the opportunity to understand the city-level calculations,” he said.
Terry says he has “bothered” Lee “a million times” about becoming a candidate for political office himself one day.
“He'd be great. He's what we need. But it's hard to convince him of that. He knows better than anyone the cost to the family. He was always close to his mother,” Terry said. “But you could tell there were parts of that life that were really hard for him.” “.
Dr. Elwyn Lee admitted that his wife's frequent absences affected Jason and his sister Erica Lee Carter.
“It's always hard for children when their mother isn't around like other mothers. You've been a great father, but they still miss their mother,” Elwyn Lee said. “But when he came to understand what she was doing and why she did it, he began to look at it in a different light.” A little different because he understood the reason for the sacrifice. He was interacting with people who I had done so much for. He realized how valuable that was.”
President Joe Biden takes a selfie with U.S. Rep. Sheila Jackson Lee, Democrat of Texas, after delivering the State of the Union address last February.
Jacqueline Martin/Getty Images
Family crisis
When Sheila Jackson Lee was diagnosed with pancreatic cancer and given only a few months to live, it was Jason Lee who convinced his mother to be more specific about announcing her medical condition and diagnosis. Elwyn Lee said he wrote the heartfelt letter sent in her name to her constituents in Houston.
“There was weight loss. You could tell she was weak and frail and having trouble moving. It was clear that something was going on. But my wife was a very secretive person. She didn’t “She didn’t want people to know she was sick.”
“Jason was very firm in his belief that you needed to be more specific than she wanted to be. He knew that if you made something public and asked for privacy because of your condition, people would be crawling around trying to figure it out, and that wouldn't be good. By being Specific and just by naming cancer, people have been given the ability to connect with it.
President Joe Biden was among those who paid their respects as Jackson Lee lay in state at Houston City Hall. Vice President Kamala Harris delivered the eulogy at the funeral, praising Jackson Lee as a “social justice warrior.”
Jason Lee planned the funeral and mustered up the courage to pay tribute to his mother who still made his father cry.
“He was the one who was in the room when she died. He talked about how, in her last moments, she wanted to know: Was she a good mother?” the elder Lee said, his voice breaking.
“He said: Yes, mother.” I was a good mother. With this mental strength, he was able to do it without crying. But it made everyone cry.”
Erica Lee Carter is serving out the remainder of her mother's term in Congress, having won that special election in which her brother voted. She's sure 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 for progress and change is what drives him,” Carter told me.
