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Paul Vallas Blasts Chicago Teachers Union, Questions Billionaire Influence in Mayoral Race During “Two Guys on Politics” Podcast
Former Chicago Public Schools CEO joins Ray Hanania and former Congressman Bill Lipinski on their Video Podcast “Two Guys on Politics” to discuss Chicago’s 2027 mayoral election, school finances, President Trump’s handling of Ukraine and the growing influence of money in politics. Video posted below.
CHICAGO — October 17, 2026 — Former Chicago Public Schools CEO Paul Vallas delivered a sharp critique of the Chicago Teachers Union, Mayor Brandon Johnson and the influence of wealthy political donors during an appearance Saturday on the Two Guys on Politics podcast hosted by political columnist Ray Hanania and former Congressman Bill Lipinski.
The three discussed Chicago’s upcoming mayoral election, the financial challenges confronting city government and public schools, and President Donald Trump’s policies toward Russia and Ukraine.
Vallas, who previously led school systems in Chicago, New Orleans and Connecticut and ran for Chicago mayor in 2023, argued that the city’s financial problems have been aggravated by the Chicago Teachers Union (CTU), which he accused of exercising excessive political influence.
“Whoever the next mayor is, if the Chicago Teachers Union has control of the elected school board, you don’t wanna be mayor,” Vallas warned. “Every single year you’re gonna have a financial crisis because you’re gonna be out there trying to bail out the schools.”
Vallas said the union has moved beyond its traditional role of representing educators.
“They’re not a union anymore. They are a left-wing political party,” he declared.
He argued that Chicago’s financial problems extend beyond pensions and employee compensation, citing increased spending on contractual services and financial support for Chicago Public Schools.
Vallas claimed the city provided schools with an additional $1.3 billion last year, beyond their existing property tax revenues. He contrasted that with his tenure leading CPS alongside Gery Chico, when he said the district operated without comparable supplemental city funding.
Lipinski agreed that the CTU has become unusually influential, although he distinguished it from other labor organizations.
“I assumed everyone knew that the teachers’ union had enormous influence in the city of Chicago, and in the Board of Education,” Lipinski said, adding that other unions have suffered from the city’s political and financial priorities.
Hanania questioned whether the relationship between Johnson and the union that helped elect him creates an inherent conflict of interest.
“The unions have a major role to play in politics, but when they put a candidate in who runs the government that they have to negotiate with for wages and for benefits and stuff, it seems like the system’s jacked,” Hanania said.
Vallas questions billionaire influence in Chicago elections
Turning to the 2027 mayoral election, Vallas criticized wealthy political donor Michael Sacks, accusing him of attempting to influence both the mayoral contest and the leadership of Chicago’s elected school board.
“Michael Sacks is trying to pick the next mayor, and he’s trying to pick the next school board president. Pure and simple,” Vallas said.
Vallas alleged that Sacks was using his financial influence to support Secretary of State Alexi Giannoulias for mayor and Jessica Biggs for school board president.
He also criticized Giannoulias’ political record and raised allegations involving his previous service as Illinois treasurer, banking connections and campaign contributions. These were Vallas’ allegations during the discussion, not independently established findings.
Vallas said other potential mayoral contenders deserved consideration, including Susana Mendoza, John Kelly and Maria Pappas. He also praised Victor Henderson as a stronger candidate for school board president.
Hanania raised the possibility that Sacks’ opposition to Johnson was influenced by political disagreements over Israel and the Gaza conflict. Vallas rejected framing the donor’s political activity primarily through that issue.
“He’s an influencer who has used his money to buy influence and to elect people and to keep people in office,” Vallas said.
Vallas argued that Sacks’ political activity reflected a broader pursuit of influence rather than a single foreign-policy issue.
Lipinski expressed reservations about Giannoulias’ advertising, arguing that commercials financed through his secretary of state campaign appeared designed to build support for a mayoral bid.
Hanania questioned whether Giannoulias was emphasizing national partisan issues at the expense of Chicago’s immediate problems.
“What about taxes? What about the economy? What are you gonna do? I haven’t seen any of that,” Hanania said.
Johnson’s political future
Lipinski suggested Johnson faces a difficult reelection campaign because of his limited experience managing city government.
“I think Johnson’s big problem is and was that he was really an amateur in politics,” Lipinski said.
He acknowledged that Johnson had become increasingly visible at public events but questioned whether those appearances could overcome voter dissatisfaction.
“I really don’t see how he manages to recover,” Lipinski said.
Vallas offered a similarly critical assessment while acknowledging that Johnson inherited longstanding financial and administrative problems.
“Brandon Johnson and I agree on one thing, that he inherited a lot of problems. The only problem is he’s made things significantly worse,” Vallas said.
Vallas also blamed former Mayor Rahm Emanuel for contributing to the city’s difficulties, arguing that Chicago’s problems predated both Johnson and Lori Lightfoot.
Asked whether he might enter the next mayoral contest, Vallas said he had promised his wife he would not run again, although he jokingly left a small opening by adding, “You never know.”
Trump, Putin and the war in Ukraine
The discussion opened with Hanania questioning Trump’s approach to Russia and Ukraine, particularly whether efforts to reduce attacks on Russian oil facilities were intended to lower energy prices before the November midterm elections.
Vallas said he believed Trump’s actions were motivated partly by domestic political considerations, but rejected suggestions that Trump was controlled by Russian President Vladimir Putin.
“Trump’s a salesman, and Trump seems to think, often naively, that he can negotiate with anyone,” Vallas said. “To a certain extent, he’s really out of his league in that respect.”
Vallas acknowledged that Ukraine had received additional lethal weapons under Trump, but argued that the president was concerned about rising gasoline prices.
“It’s definitely an election year move,” Vallas said.
Lipinski doubted the strategy would produce meaningful economic benefits before Election Day.
“I don’t think there’s time to do that, Ray,” Lipinski said, arguing that any substantial reduction in gasoline prices would have needed to occur months earlier.
Lipinski also praised Ukrainian President Volodymyr Zelenskyy’s wartime leadership and criticized Trump’s suggestion that Ukraine needed new leadership.
“I think this guy has done a hell of a job leading his country,” Lipinski said.
Independent journalism and political cooperation
The conversation concluded with a discussion of veteran Chicago columnist John Kass, whose health problems have affected his publishing schedule.
Vallas, a regular contributor to Kass’ publication, said he hoped Kass would continue writing and participating in political commentary.
Hanania recalled helping Kass gain access to the Chicago City Hall press room early in his journalism career.
The participants also emphasized the importance of independent journalism and the declining willingness of politicians to work across party lines.
Lipinski recalled cooperating with Republican leaders on major transportation and infrastructure projects during his congressional career.
He concluded by calling for political leadership capable of uniting Americans across ideological divisions.
Discussing his latest column, Lipinski said the country needed a president combining the qualities of George Washington, Abraham Lincoln, Franklin Roosevelt, and Ronald Reagan.
The October 17 episode was Season 5, Episode 28 of Two Guys on Politics, available at TwoGuysOnPolitics.com.
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For more information OPaulk Vallas visit https://www.chicagocontrarian.com/writers/paul-vallas
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Hanania also writes about Middle East issues for the Arab News, and The Arab Daily News criticizing government policies in the Israeli-Palestinian conflict.
Hanania was named "Best Ethnic American Columnist" by the New America Media in November 2007, and is the 2009 recipient of the SPJ National Sigma Delta Chi Award for column writing.
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