Illinois’s two new taxes aimed at the digital economy do not take effect until January 1, 2027. They are already in court.
On September 11, 2026, NetChoice filed two separate complaints in the Circuit Court of Cook County, Chancery Division,
Jake Leahy Blogs
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Forced Annexation in Illinois: Supreme Court to Decide Whether a Boundary Gap Can Be “De Minimis”
Illinois municipalities have several ways to annex unincorporated property. One of the most consequential is Section 7-1-13 of the Illinois Municipal Code, which permits a municipality, without a landowner’s consent, to annex certain unincorporated territory containing 60 acres or less
IRS Notice 2026-28: New Guidance on Calculating the Paid Family and Medical Leave Credit
The federal employer credit for paid family and medical leave was scheduled to expire after 2025. Congress instead made the credit permanent and substantially changed how employers may calculate it. For taxable years beginning after December 31, 2025, an eligible
When Does Government Regulation Become an Unconstitutional Taking? The Seventh Circuit’s Answer After Tyler
The Supreme Court’s decision in Tyler v. Hennepin County arose from a property tax foreclosure. Its influence may extend well beyond delinquent taxes.
In BBLI Edison, LLC v. City of Chicago, No. 25-1713 (7th Cir. July 22, 2026), the
First-in-the-Nation Illinois Digital Asset Tax Faces Constitutional Challenge
The first major legal challenge to Illinois’ newly enacted Digital Asset Tax Act has arrived.
On July 21, 2026, the Chamber of Digital Commerce d/b/a The Digital Chamber filed a lawsuit in the Circuit Court of Sangamon County seeking to
Can Illinois Tax Prediction Markets? Kalshi’s Federal Lawsuit Tests the Boundary Between Sports Wagering and Federal Derivatives Law
Illinois has joined the growing national fight over prediction markets. It did so through Senate Bill 3019, a revenue and gaming measure that attempts to bring sports-related prediction-market contracts within the Illinois Sports Wagering Act. KalshiEX LLC has now
Settlement Agreements, Forms 1099, and Tax Trouble: Lessons from Adusei v. Auer
A recent federal decision out of Arizona offers a useful reminder about the tax treatment of settlement payments, as well as risks that arise when settlement agreements fail to address tax characterization clearly.
In Adusei v. Auer, a former
IRS Announces New Conservation Easement Settlement Initiative as Litigation Pressure Mounts
The IRS announced a new time-limited settlement initiative for conservation and historic preservation easement cases, offering reduced penalties amid continued government success in Tax Court litigation.
United Center’s 1901 Project Shows How Chicago Property Tax Incentives Really Work
The United Center’s 1901 Project is seeking a Cook County Class 7(b) property tax incentive. Here is how the incentive works, how the project appears to qualify, and why it differs from the Bears stadium tax fight.
IRS Grants Late Section 754 Election Relief After Partner’s Death: Practical Lessons for Partnerships
In PLR 202619013, the IRS gave a partnership 120 days to make a late Section 754 election after a partner died. The ruling is useful, but not because it creates precedent. Its practical value is the reminder that late relief