Jake Leahy

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Just this morning, the IRS just announced a new, time-limited settlement initiative for conservation easement and historic preservation easement cases. And the agency is making clear that it views continued litigation as increasingly risky for taxpayers.
The new initiative offers eligible taxpayers significantly more favorable terms than the results taxpayers have generally achieved in Tax Court. Under the program, eligible partnerships may resolve cases with no charitable contribution deduction, but with an “other deduction” for approximate out-of-pocket costs and a substantially reduced gross valuation misstatement penalty, that is, 10% during the initial 90-day window, increasing to 20% during a subsequent


Continue Reading IRS Announces New Conservation Easement Settlement Initiative as Litigation Pressure Mounts

The proposed tax break for the United Center’s 1901 Project has been described as a $55 million subsidy for the owners of the Chicago Bulls and Chicago Blackhawks. That is understandable shorthand, but it is not the precise tax mechanism.
The proposal is a Cook County Class 7(b) property tax incentive. It does not write the owners a check. It would reduce the property’s assessment level for 12 years, which in turn lowers the property tax bill that would otherwise apply to the first phase of the project.
That distinction is key, because Class 7(b) is an existing Cook


Continue Reading United Center’s 1901 Project Shows How Chicago Property Tax Incentives Really Work

The IRS released PLR 202619013 on May 8, 2026. A limited partnership taxed as a partnership had a partner die. The partnership inadvertently failed to make a Section 754 election for the relevant tax year. The partnership then requested late-election relief under Treas. Reg. § 301.9100-3. The IRS granted the partnership 120 days from the date of the letter to make the election effective for that year.
A Section 754 election allows partnership property basis adjustments under Section 734(b), for certain distributions, and Section 743(b), for certain transfers of partnership interests. The election is made by


Continue Reading IRS Grants Late Section 754 Election Relief After Partner’s Death: Practical Lessons for Partnerships

Federal law generally prohibits candidates from using campaign funds for personal expenses. But under a narrow exception administered by the Federal Election Commission, certain nonincumbent federal candidates may receive compensation from their campaign committees during the course of a campaign.
The rule is intended to make federal office more accessible to candidates who otherwise would lose income by leaving employment or reducing work to campaign full-time. At the same time, the FEC has repeatedly emphasized that campaign salary is not a general living stipend and cannot become a mechanism for converting campaign funds into personal income.
That tension explains why


Continue Reading Can Federal Candidates Use Campaign Funds to Pay Themselves?

Alexander County had the highest annual average unemployment rate in Illinois in 2025 at 6.8%, followed by Pulaski County at 6.0% and Macon County at 5.8%, according to the Illinois Department of Employment Security. Monroe County had the lowest rate at 3.0%. Statewide, Illinois’ annual average unemployment rate was 4.6%, compared with 4.3% nationally.
A county unemployment rate is not the same thing as the percentage of adults without jobs. IDES reports these figures through the Local Area Unemployment Statistics program, which estimates the labor force, employment, unemployment, and unemployment rate for counties and other local areas. The unemployment


Continue Reading Illinois County Unemployment Rates 2025: Full Ranking from Highest to Lowest

Illinois’ first-in-the-nation Interchange Fee Prohibition Act has become more than a dispute over credit card “swipe fees.” It has since evolved into a test of state authority, federal banking preemption, payment-card infrastructure, and the practical limits of regulating national payment systems one state at a time.
The Illinois Interchange Fee Prohibition Act or IFPA, is scheduled to take effect on July 1, 2026. In general terms, the Act prohibits an interchange fee from being charged or received on the portion of a credit or debit card transaction attributable to taxes or gratuities. That means, for example, that if a customer


Continue Reading Illinois Swipe Fee Law Update: Federal Agency Action Adds Uncertainty Before July 1

A proposed Illinois constitutional amendment that would impose a 3% surtax on income over $1 million is no longer just an introduction. It is now moving through the House.
As of yesterday (April 21, 2026), the resolution passed out of the House Revenue & Finance Committee (13–7) and has been read a second time, where it now sits on the House calendar for short debate. A hearing is also scheduled, signaling that leadership is at least willing to keep the proposal in play.
Substantively, the measure remains straightforward. It would amend the Illinois Constitution to impose an additional 3% tax


Continue Reading Illinois “Millionaire Surtax” Draws Opposition from Business Groups as Amendment Advances

On April 6, the Supreme Court denied certiorari in Stroble v. Oklahoma Tax Commission. The denial leaves in place an Oklahoma Supreme Court decision allowing the State to tax a Muscogee (Creek) Nation member who works for the Tribe on trust land but resides on unrestricted fee land within the reservation recognized in McGirt.
The question presented was ultimately not whether McGirt recognized a reservation (it did) but instead, whether that recognition carries through to state income taxation. The Oklahoma Supreme Court answered no. The Court declined review.
Arguments Presented on the Petition for Certiorari
The amicus brief filed by


Continue Reading Supreme Court Denies Certiorari in Stroble v. Oklahoma Tax Commission

Illinois lawmakers are moving to regulate, and heavily tax, prediction markets. Prediction markets are a fast-growing corner of online wagering that has largely operated outside traditional gaming frameworks.
Senate Bill 4168, introduced by State Sen. Michael Hastings on March 5, 2026, would create a new Prediction Markets Regulation and Taxation Act, requiring any platform offering prediction contracts to Illinois users to obtain a license from the Illinois Gaming Board and pay a $1 million upfront fee and $1 million annual renewal.
The bill is currently pending in Assignments and State Sen. Cristina Castro has been added as a


Continue Reading Illinois Bill Targets Prediction Markets With 50% Tax and $1M License Fee (SB 4168)

On March 11, 2026, Cheesie’s Wicker Park filed a Petition at the Illinois Independent Tax Tribunal challenging a “Notice of Tentative Denial of Claim” issued by the Illinois Department of Revenue for Sales/Use Tax & E911 Surcharge.
Cheesie’s Wicker Park, LLC alleges it overpaid sales tax for the period January 2021 through November 2021 by including tips in taxable receipts and failing to account for tax already remitted through a marketplace facilitator. The company filed ST-1-X Amended Sales and Use Tax and E911 Surcharge Returns seeking approximately $46,453 in credits.
The Department’s September 2, 2025 Notice of Tentative Denial of


Continue Reading Illinois “Notice of Tentative Denial of Claim” Dispute: Sales/Use Tax & E911 Surcharge Refund Challenge

On March 6, 2026, Jeffrey Somers filed a Petition at the Illinois Independent Tax Tribunal challenging Illinois income tax assessments for tax years 2018 and 2019.
The petitioner, Jeffrey Somers, alleges that he was a California resident who performed all services remotely from California and had no physical presence in Illinois during the years at issue. He contends that his wages were incorrectly reported as Illinois-source income on Forms W-2 due to his employer’s Illinois headquarters, leading to an improper assessment by the Illinois Department of Revenue.
The Department issued Notices of Deficiency totaling approximately $53,000 in tax and interest


Continue Reading Illinois Remote Work Tax Dispute: California Worker Challenges Illinois Income Tax Assessment

Earlier this week, Lake County Judge Luis A. Berrones ruled that the name of Lake County Board candidate Juan Beto Ruiz (Reynoso) should not be on the ballot. The Lake County Clerk has already printed ballots with the name of candidate Ruiz on them. Ruiz is challenging incumbent Esiah Campos; and his name has been printed as Juan Beto Ruiz. But his full legal name is Juan Beto Ruiz Reynoso. Unless Ruiz appeals, any ballots cast for him will not be counted.
Under the Illinois Election Code, candidates may use given names, initials, or commonly known nicknames when filing nomination


Continue Reading Can a Candidate Be Removed From the Ballot for Not Using Their Full Legal Name in Illinois?

Earlier this week, the U.S. Supreme Court clarified an important question in sovereign immunity law: when does a state-created entity qualify as an “arm of the State” entitled to share the State’s immunity from suit? In a unanimous 9–0 decision authored by Justice Sotomayor, the Court held that the New Jersey Transit Corporation is not an arm of the State of New Jersey and therefore cannot invoke the State’s sovereign immunity in out-of-state lawsuits. Galette v. New Jersey Transit Corp.
The case arose from two accidents involving New Jersey Transit buses: one happened in New York City, and the


Continue Reading When Is a State-Created Entity an “Arm of the State” for Sovereign Immunity?

The First District Appellate Court has confirmed the removal of Joseph “Joe” Severino and Rantch Isquith from the March 17, 2026 Republican primary ballot for Governor and Lieutenant Governor after they failed to meet the 5,000-signature requirement for statewide candidates. Severino v. Illinois State Board of Elections, 2026 IL App (1st) 260151-U (Feb. 20, 2026).  While the case is not groundbreaking, it is instructive to future candidates.
The candidates filed nomination papers containing 6,336 signatures. An objector challenged 2,520 of them. After a records examination, the State Officers Electoral Board sustained objections to 1,588 signatures, leaving the candidates with


Continue Reading Illinois Appellate Court Affirms Ballot Removal of Gubernatorial Candidates for Falling Short of 5,000 Signatures

Yesterday the Supreme Court decided GEO Group, Inc. v. Menocal, 607 U.S. ___ (2026), holding that the federal contractor doctrine recognized in Yearsley v. W.A. Ross Construction Co., 309 U.S. 18 (1940), is a merits defense rather than an immunity from suit. Because it is a defense to liability and not a right to avoid litigation altogether, a district court’s rejection of the defense cannot be immediately appealed under the collateral-order doctrine.
The decision is nominally about government contractors. Its real significance is about appellate timing and litigation leverage. The Court sharpened the line between arguments that defeat


Continue Reading When Can a Defendant Immediately Appeal a Denied Defense in Federal Court?

A complaint filed February 24, 2026, with the Federal Election Commission alleges that Daniel Biss, his principal campaign committee (Biss for Congress), and his state committee (Friends of Daniel Biss) violated the Federal Election Campaign Act by using nonfederal funds in connection with a federal election. See Complaint, Fine v. Biss, FEC Complaint (Feb. 24, 2026).
The complainant, Carol Ronen, asserts that Biss is simultaneously a candidate for U.S. House in Illinois’s 9th Congressional District and for Democratic State Central Committeeman. According to the complaint, Friends of Daniel Biss, which is rasiing money for the state central committee race


Continue Reading FEC Complaint Alleges Use of Nonfederal Funds in Illinois 9th District Congressional Race