Chicago billionaire Michael Sacks has sent a legal cease-and-desist letter demanding that an advertising firm stop soliciting, ghostwriting, financing, publishing or republishing false or misleading statements about him, escalating a fight over paid influencer content just weeks before the city's first-ever citywide vote for Board of Education president. The letter, sent through Sacks' attorney, accuses the firm Good Influence of soliciting false, misleading and defamatory statements about Sacks tied to the November school board race.
According to the Chicago Tribune, Good Influence — an advertising firm that connects clients with social media influencers — received the letter. The letter was sent on September 14. The firm had solicited videos discussing Sacks' involvement in Chicago politics, including posts criticizing him and posts supporting Hilario Dominguez's campaign for Board of Education president, per the Tribune's reporting. Sacks' attorney, Ed Siskel, demanded that Good Influence immediately stop soliciting, ghostwriting, financing, publishing or republishing false or misleading statements about his client. Siskel brings considerable institutional weight to the fight: he began serving as White House Counsel under President Joe Biden in September 2023, previously worked as Deputy White House Counsel under President Barack Obama, and served as Corporation Counsel for the City of Chicago under Mayor Rahm Emanuel, according to Wikipedia.
A Proxy Fight Over the School Board Presidency
The dispute lands squarely inside a high-stakes contest for the only seat on Chicago's new 21-member Board of Education elected citywide. That race already forced one candidate, Jennifer Custer, to drop out in August 2026 over what she called millions in special-interest spending, Hoodline previously reported. Dominguez, the candidate Good Influence's pitch materials sought to promote, served as the Chicago Teachers Union's political director, and roughly 99.4% of the money he had raised to date came from the CTU, according to A City That Works. Dominguez is a former CPS special education teacher, per the same account.
Per the Tribune's reporting, Good Influence's proposed messaging mentioned Sacks by name, and the firm sought posts framing him as an opponent of Dominguez's candidacy. The Tribune notes that identity of the party ultimately behind any published videos remains unclear, and whether Good Influence's solicitation directly prompted social media criticism of Sacks also remains unclear.
Sacks' Ties to Chicago Power Politics
Sacks, CEO of investment firm GCM Grosvenor, served as a top advisor to former Chicago Mayor Rahm Emanuel and has advanced Democratic causes including gun control, the Tribune reports. He led the committee that raised funds for the 2024 Democratic National Convention in Chicago. He also helped raise $10 million to launch Common Ground Collective, a political action committee that has spent heavily opposing Mayor Brandon Johnson and his progressive allies, according to the Tribune's account, and Sacks added more than $900,000 to that PAC in September 2026.
Common Ground Collective's involvement in this race is not new. The group spent over $840,000 alongside corporate allies in March 2026 backing Democrat State Rep. Jaime Andrade, who ultimately lost to CTU-backed candidate Miguel Alvelo Rivera, according to the Illinois Times. Tensions between Sacks and CTU leadership had already surfaced by May 2026, when CTU President Stacy Davis Gates circulated a delegate letter criticizing Sacks, while Sacks published an op-ed defending AIPAC, per the Northside GOP Club. The Tribune separately reports that Sacks contributed $1.2 million to AIPAC-organized PACs. Sacks also contributed $500,000 to Alexi Giannoulias, Illinois Secretary of State and a top opponent of Johnson, the Tribune reports.
Mayor Johnson's Criticism and the Antisemitism Dispute
Mayor Johnson has cast Sacks as a central opponent in his own mayoral race, saying his opponents get money from Sacks, corporate interests, billionaires and millionaires, per the Tribune. Sacks' legal letter separately argued that a public smear campaign attributing the closure of 50 Chicago schools under Rahm Emanuel's administration to Sacks was false, and suggested that Johnson's criticism of Sacks evoked antisemitic stereotypes. The Jewish United Fund called on Johnson not to use Jewish Chicagoans as political foils and condemned his remarks as dangerous and irresponsible, according to the Tribune's reporting.
Crystal Gardner, identified in the Tribune's report among Sacks' critics, compared Sacks to Donald Trump and Elon Musk and accused him of using his power to protect his wealth and ego while trying to censor critics. Gardner said critics would not stay silent about Sacks, the Tribune reports. Sacks faces increasing attacks from Chicago's political left, according to the same account.
Good Influence's Response and the Disclosure Gray Area
Good Influence's spokespeople pushed back on the demand. CEO Stuart Perelmuter and president Josh Cook lead the firm, which the Tribune describes as requiring that any influencer partnership be clearly disclosed. Cook said the firm considers the matter closed and denied that Good Influence is liable for the purported false statements about Sacks, while the firm asserted indemnification rights against Mori Strategies, a Washington, D.C.-based political consulting firm that had contracted Good Influence for the work, per the Tribune. Becky Carroll, Sacks' spokesperson, said a paid influencer campaign targeting Sacks is not organic and contains lies and defamation, according to the Tribune.
Financial records cited by the Tribune show the Chicago Teachers Union paid Mori Strategies $23,543.34 and separately $33,455.79 for professional services. Good Influence is an advertising firm that connects clients with social media influencers.
The dispute highlights disclosure questions surrounding paid political influencer posts. Influencers are playing a growing role in Chicago politics.
A Board Already Tightening the Rules
Chicago's Board of Education has been trying to get ahead of outside money flooding the race. In July 2026, the board voted 16-1 to ban all school board candidates from accepting campaign contributions from current or prospective CPS vendors or outside board counsel, Hoodline previously reported. The board's finances remain contested on other fronts too: in July 2026, it approved a budget that passed 11-7 and relied on $150 million in projected, uncommitted state revenue, a budget fight Hoodline covered in its reporting on the budget fight.
Whether any paid influencer videos were actually posted before Sacks' legal demand remains unclear, and whether Mori Strategies or CTU directly authorized the influencer outreach has not been established. How election authorities will ultimately evaluate dark-money influencer spending under existing campaign finance disclosure laws is an open question that could shape how future Chicago races are fought online.
