Meet the Lawyers Who Thrust Chicago Transfer Tax into Limbo

When real estate industry groups decided to challenge the city’s transfer tax referendum in court, they didn’t hire just any attorneys for the job.

They found two well-connected lawyers, each with long histories representing high-profile clients in Chicago and throughout Illinois, including former Mayor Rahm Emanuel and former Secretary of State Jesse White.

The result was a win for real estate Friday, when a Cook County Circuit Court judge invalidated the city’s ballot question asking voters to implement a tiered transfer-tax structure aimed at funding services to prevent homelessness.

Michael J. Kasper, the trade groups’ lead attorney on the case, is an election law expert who specializes in constitutional law and previously served as general counsel for now-disgraced former Illinois Speaker of the House Michael Madigan. Kasper has represented “hundreds” of big names in high-profile cases, including former U.S. presidents Barack Obama and Bill Clinton, according to his firm’s website.

Kasper’s co-counsel in the transfer tax suit, Michael Del Galdo, has made a name for himself working on cases related to state and local governmental matters. He is the founding attorney of Del Galdo Law Group, a firm with 25 attorneys that serve as counsel for municipalities across suburban Cook County.

Del Galdo and Kasper declined to be interviewed Wednesday, stating they do not speak to the media while a case is ongoing — both City Hall and the Chicago Board of Elections have appealed Judge Kathleen Burke’s ruling that gave real estate a win.

The two attorneys sued the Chicago Board of Elections in January on behalf of a slew of real estate trade groups, led by the Building Owners and Managers Association of Chicago.

In a Feb. 14 hearing before Burke, Kasper and Del Galdo successfully argued that the phrasing of the transfer tax referendum wasn’t legal to pose to voters. They claimed Illinois law prohibits what they called “legislative logrolling,” which refers to packaging controversial policies with popular ones. The restriction is meant to protect voters from having to decide on ballot measures that would turn both popular and unpopular policies into law with one action.

The question will still appear on the March 19 ballot, but the votes will not be counted for the time being. It asks voters about both a tax decrease for sales prices under $1 million and an increase for real estate deals totaling $1 million or more.

Shortly before the Feb. 14 hearing, the city moved to intervene in the lawsuit, in part, on the grounds that the Chicago Board of Elections was not the right party to sue and could not adequately defend the case because of its lack of knowledge of the Illinois Constitution and Illinois Municipal Code. In a court filing, the Chicago Board of Elections itself said it did not have the jurisdictional authority to be arguing the case.

Meanwhile, Kasper and Del Galdo are highly specialized in these exact areas.

The lawsuit against the transfer tax referendum, known as Bring Chicago Home, wasn’t Kasper’s first foray into challenging ballot initiatives, either. In 2016, he successfully argued a case in front of the Illinois Supreme Court to remove a ballot measure that would have created an independent process for redistricting, by putting it into the hands of an 11-member commission rather than the state legislature. Similar to the transfer tax case, Kasper argued that the ballot question violated the Illinois Constitution.

Many of the governmental matters Del Galdo has worked on throughout his career are directly related to real estate, including zoning, tax increment financing, economic development, land use and permitting, according to his firm’s website.

Del Galdo’s Berwyn-based firm provides counsel to the towns of Berwyn as well as Melrose Park, Broadview, Chicago Heights, Stickney and others, according to reporting by the Cook County Record. In 2015, the Better Government Association found that Del Galdo’s firm was among the highest paid by Cook County towns, pulling in $14.8 million between 2010 and 2015.

His firm represents various local governments with combined budgets of over $1 billion, according to a biography provided by his spokesperson.

Del Galdo was accused of being part of an “insider deal” when he was hired by the Cook County Land Bank Authority in 2021, while allegedly living with the top aide to Bridget Gainer, the county commissioner who founded the authority and chairs its board, the Chicago Sun-Times reported.

He has left his mark on nearly all areas of local and state government, providing counsel to park districts, representing towns on large-scale redevelopments and drafting multiple state laws to increase the “police powers of local governments,” according to his biography.

In 2013, Kasper came in at No. 59 on Chicago Magazine’s list of the 100 most powerful people in the city. It cited his previous role as general counsel for Madigan, calling Kasper a “big man on campus in Springfield.”

Kasper was also the lead attorney in defending the residency challenge of former Mayor Emanuel in 2011 and served as Illinois House Prosecutor in the 2009 impeachment trial of former Gov. Rod Blagojevich.

Beyond his experience as an attorney, Kasper is also known for his work lobbying City Hall. When then-Mayor Emanuel’s administration made lobbyist data available online in an effort to improve transparency in 2011, Kasper and his associates — Courtney Nottage and, at the time, David Dring — were listed as having taken in almost $236,000 over a 6-month period to “lobby the mayor, alderman and others,” the Chicago Tribune reported. The firm’s lobbying clients included Advocate Health Care Network and Apple.

Kasper also supported the campaign of his late wife, Laura C. Liu, who was the first Chinese-American judge in Illinois history and became the first Asian-American to serve in the Illinois Appellate Court after being elected to the 1st District in 2014. She had breast cancer and died at age 49 in 2016.

Kasper lives in Lincoln Park with his wife Kerry and their two daughters, according to his firm’s website. He is an alumnus of Northwestern University School of Law and the University of Notre Dame, and he grew up on the South Side of Chicago.

Del Galdo went to Drake University in Des Moines before attending law school at DePaul University, according to his biography.