When Houston mayoral candidate Sheila Jackson Lee visited Chicago to fundraise last year, she found a faithful ally in Mayor Brandon Johnson.
Standing onstage at an August fundraiser in the West Loop, Johnson applauded their shared progressive values. Then he made a more unique appeal on behalf of the longtime Democratic congresswoman, noting to the crowd her connection to one of his most important City Hall advisers, according to a recording posted on YouTube.
“Now, my senior adviser and the political brain trust that really has affirmed my conscience is the son of the next mayor of Houston, Texas,” Johnson said, referring to his top aide Jason Lee.
Johnson continued: “And so if the son of Houston, Texas, can elect a mayor in the city of Chicago, well, Chicago, we got to make sure that Houston elects Sheila Jackson Lee as the next mayor of the city of Houston.”
Jackson Lee would go on to get a financial boost in her Texas campaign from Chicago City Hall insiders, bringing in more than $51,500 from city contractors, lobbyists and politicians between that August fundraiser and her loss in the December runoff, a Tribune analysis found. In total, her mayoral campaign raised $77,600 from donors with Illinois addresses.
That group includes a prominent entrepreneur with city business dating back to the Daley era, a lobbyist for the White Sox, a former Cook County assessor who’s now a real estate attorney and multiple developers with ongoing city-funded projects. Several have active business with City Hall.
None of the 20 contributors from Chicago had previously given money to a Jackson Lee campaign during her nearly three decades in the U.S. House.
All the while, Jackson Lee’s son was emerging as a key member of Johnson’s nascent administration and quickly gained a reputation as a powerful decision-maker behind the scenes.
There is no evidence Jason Lee urged the Chicago contributors — a handful of whom said they were already familiar with Jackson Lee from her time in Congress — to give her money. But the Chicago-to-Houston campaign funding pipeline presents an unusual situation where local figures who stand to gain from having a close relationship with Johnson’s inner circle have a new path to curry favor.
“This is the problem with the way our campaign finance system works. It’s always hard to tell what people’s motivations are when they donate, so it leaves open these types of questions,” Reform for Illinois executive director Alisa Kaplan wrote in a statement. “It definitely merits a closer look.”
In a phone interview, Lee told the Tribune he did not solicit any contributions or support for his mother in Chicago and had no role in her mayoral campaign besides attending the local fundraisers, where he said he did not give remarks but may have been introduced as her son.
“None of this had anything to do with me,” Lee said. “And most people in Chicago who are involved in politics have known about my mom or know my mom personally for far longer than they’ve known me. And for most of the time that I’ve lived in Chicago — almost all the time I lived in Chicago — no one even knew that was my mom.”
Lee had cut his teeth on organizing for Chicago grassroots and labor groups before helping usher the future mayor into his first elected office during Johnson’s 2018 campaign for Cook County commissioner. When it came to his mother’s political ambitions, Lee said he was “back seat completely,” and the August fundraiser was a “pretty standard” show of Chicago’s mostly Black political class rallying behind a national African American mayoral candidate visiting from out-of-state.
But while it’s clear Jackson Lee has formidable name recognition in her own right, her ties to Johnson’s inner circle have not gone unnoticed.
In November, Cook County Metropolitan Water Reclamation District Commissioner Kari Steele posted a Facebook photo with Jackson Lee captioned, “I’m with Sheila!” Underneath, a user commented, “This should make a certain Brandon Johnson staffer very happy.”
A native of Houston, Steele replied to that person and clarified that she has followed Jackson Lee’s career since high school. But the original remark shows how even without confirmation of pay-to-play politics, some may still be reminded of Chicago’s infamous, unofficial political slogan: “We don’t want nobody nobody sent.”
“It’s concerning because there’s a possibility of bad faith,” Kent Redfield, a political science professor emeritus at the University of Illinois Springfield, said. “I have no reason to believe (Jason Lee) isn’t acting honorably and ethically, but that doesn’t make the situation go away.”
Redfield said the key to discerning what Chicago-based interest in the Houston mayor’s race was “business as usual” and what was less so is looking at that individual’s contributions in other far-flung races.
To be sure, some out-of-state campaign money is indeed par for the course in major cities, and the congresswoman’s mayoral candidacy did generate excitement among supporters who wanted to elect an experienced progressive to be Houston’s first female Black mayor.
But her Chicago contributors did not back prominent mayoral candidates with similar bona fides elsewhere. Some supported Johnson’s runoff opponent, the more conservative Paul Vallas, last spring.
Only three of the 20 Chicago individuals who gave to Jackson Lee also donated to Karen Bass’ 2022 campaign for mayor of Los Angeles, even though she was also seen as a well-established, progressive congresswoman who had chaired the Black Caucus and was fundraising in Chicago, per campaign expenditure reports.
The bulk of Jackson Lee’s Chicago-area contributions were made in September, several on the same date that fell over a week after her West Loop appearance with Johnson. Her political campaign did not respond to Tribune questions about her schedule, but Lee said his mother held multiple fundraisers in the region, upon former Democratic U.S. Rep. Cheri Bustos’ recommendation.
The contributions range from $5,000 — the legal limit in Houston — to as low as $50. Active City Hall contractors are prohibited from giving directly to the mayor, per an executive order enacted by former Mayor Rahm Emanuel because he wanted to build “trust in the public and in public office.”
Chicago-based developers who opened their wallets for Jackson Lee include those with major contracts with City Hall, two who were granted city taxpayer funds for recent projects under former Mayor Lori Lightfoot’s Invest South/West initiative. That program was billed as a catalyst for pumping public dollars into disinvested neighborhoods but has been in limbo as the Johnson administration weighs how to proceed with remaining projects, according to WBEZ.
Lee did not have an update on the fate of the program beyond saying, “I don’t know, but that has nothing to do with anything. Those things have no relation to each other.”
One of the biggest players in Chicago real estate who appears in Jackson Lee’s campaign finance reports is Elzie Higginbottom, CEO of East Lake Management and Development. The longtime construction and development magnate contributed $5,000 to Jackson Lee on Sept. 11. His wife Deborah gave the same amount that day.
During the Chicago mayoral runoff season, Elzie Higginbottom gave $2,500 to Vallas. He also signed a $23.5 million contract with the CTA in March to oversee Lightfoot’s proposed Red Line extension to 130th Street. The fruits of that deal will hinge on whether the Johnson administration, which supports the project, can shore up the remaining $400 million needed.
A.J. Patton, CEO of the 548 Capital firm that saw at least three of its development plans clinch Invest South/West grants, gave $1,000 to Jackson Lee on Sept. 5.
Another Invest South/West awardee, Park Row Development co-founder Matthew Mosher, gave $500 to Jackson Lee’s mayoral campaign on Sept. 11. Prior to starting his company, Mosher was chief construction officer at the Chicago Housing Authority.
And Ryan Green, an executive with the developer DL3 Realty that has received TIF dollars and a tax break for various projects, gave the smallest amount at $50 on Oct. 18. His spokeswoman said he has no relationship with Jason Lee and had happened to meet the congresswoman during a Washington, D.C., event.
The rest of the developers did not return a request for comment.
David Orr, the former Cook County clerk and founder of Good Government Illinois, said the presence of Chicago city contractors on the out-of-state race’s campaign contributors list “certainly raises questions of appearance.”
“There may be nothing more than ‘Hey, I know so-and-so’ ... but the reason I say that it’s worth looking into is because how much we’ve seen in Chicago — over the last several decades and still continuing as we speak — of constant pay-to-play politics in certain sectors of the government,” Orr said.
Several people who registered last year with the city of Chicago as City Hall lobbyists also donated to Jackson Lee’s Houston campaign. Lisa Duarte, a registered lobbyist for the Chicago White Sox and Related Midwest — the developer of The 78 complex, where the franchise hopes to build a new stadium — gave $5,000 on Nov. 30. She did not immediately respond to request for comment.
They also include Alex Sims, a longtime Chicago political consultant who worked for Kim Foxx and Johnson during his mayoral transition; Robert Blackwell, CEO of tech firm EKI-Digital that spearheaded the City Council’s recent transition to an e-voting platform and a friend to the Obamas; Thomas Raines, who represented real estate as well as the parent companies of Instacart and Circle K in dealings with City Hall; Malcolm Weems, who worked on behalf of Xerox and other software interests; and Michael Sutton, an engineering executive.
Blackwell and Sutton did not respond to requests for comment. The other three said their interest in the Houston race had nothing to do with Jason Lee. Sims said she has known Jackson Lee for a “long time,” Raines — also a Bass donor in 2022 — said he donates to Democrats nationwide and Weems said a close mentor from Texas politics sold him on the candidate.
Also, Maze Jackson, a real estate and construction lobbyist, gave $2,500 to Jackson Lee’s mayoral bid on Aug. 31 via the National Association of Promotional Retailers, a small business lobbyist group of his. Jackson is married to Steele, the MWRD head, and told the Tribune his contribution was on Steele’s behalf.
Brad O’Halloran, the former head of Metra who resigned after patronage allegations, also gave $5,000 on Sept. 1, from an Indiana address. He did not immediately respond to requests for comment.
U.S. Rep. Danny Davis contributed $500 to Jackson Lee in Sept. 27, while former chair of the Democratic Party of Illinois U.S. Rep. Robin Kelly donated $500 to Jackson Lee on June 17, and another $500 on Nov. 8. Both of them said the support stemmed from a strong working relationship after serving in Congress together, and Kelly also donated to Bass’ mayoral campaign.
Johnson’s hand-picked vice mayor, Ald. Walter Burnett, 27th, contributed $1,000 to Jackson Lee via his Democratic ward organization on Nov. 6. Burnett told the Tribune it was not Jason Lee but others in Chicago, including Davis, who solicited him about supporting Jackson Lee.
Charles Smith, a longtime member of Johnson’s inner circle who co-chaired his mayoral transition committee, gave $500 to Jackson Lee on Sept. 1, and another $4,500 on Sept. 12. The CEO of CS Insurance Strategies was tapped by the mayor this month to serve as his key executive on World Business Chicago, the city’s agency for tourism and economic development.
Dr. Tariq Butt, a former Chicago Board of Education member, gave $5,000 to Jackson Lee on Sept 5. He gave to Vallas during the April runoff.
And Thomas Tully, the former Cook County assessor and prominent Chicago property tax and real estate attorney, donated $5,000 on Sept. 11. He contributed $5,000 to Johnson days before his inauguration.
Lastly, a $2,500 check to Jackson Lee in September came from Johnnie Chandler, CEO of a Chicago snow removal company, Polar Group LLC. (He and Smith were the other two contributors who also supported Bass’s mayoral campaign.)
Chandler does not appear to have active contracts with the city, and he also donated $5,000 to Johnson on Oct. 2.
Reached by phone, Chandler said, “I’m friends with her son and I support her and her son,” before saying he had to tend to a contractor and hanging up.