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Hon. Anna H. Demacopoulos (Ret.)

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Hon. Anna H. Demacopoulos (Ret.) is a veteran of the Cook County courts and the Cook County State’s Attorney’s Office.  She became a sought after pre-trail mediator in the Chancery Division, where she presided over complex, high stakes matters.

Her docket included class actions, shareholder derivative actions, employment and labor disputes, insurance coverage, FOIA, and other commercial litigation. She regularly handled requests for temporary restraining orders and preliminary injunctions, requiring prompt decisions under pressure and careful management of matters with significant financial and reputational implications. This experience informs her ability to guide parties through time-sensitive disputes and difficult negotiations.

Judge Demacopoulos has served as First Assistant State’s Attorney for Cook County, where she was second-in-command of one of the nation’s largest prosecutor’s offices. There, she oversaw more than 700 attorneys and 1,400 staff across criminal and civil divisions and advised on significant legal and policy matters. In this role, she advanced the office’s mission through restructuring, modern policies, and specialized units in forensics, financial crimes, and sexual assault, enhancing collaboration and restoring trust in the criminal justice system. On the civil side, she oversaw the county’s representation in disputes involving taxation, employment and labor, and civil rights, and advised elected officials on legal and policy issues.

Judge Demacopoulos is an experienced mediator who helps parties focus on the core issues and move toward resolution.  She works with counsel and clients to reach clear, practical, and durable resolutions in complex disputes.

Representative Matters

As a judge, she has handled a wide variety of matters, including:

Administrative Law

  • Settled matter involving violations of the City of Chicago Ethics Ordinance by an employee of the Civilian Office of Police Accountability, Lee v. City of Chicago 20CH4524
  • Settled matter involving revocation of a liquor license, CH House Corp. v. Illinois Liquor Control Commission 23CH00620
  • Presided over matter involving revocation of a gaming license where licensee alleged violation of due process and Open Meetings Act, Illinois Interactive Gaming, LLC v. Illinois Gaming Board 17CH13232
  • Presided over an applicant's constitutional challenges to the Conditional Adult Use Dispensing Organization Licenses under the Illinois Cannabis Regulation and Tax Act (CRTA), Big City Ventures v. IDFPR 21CH3921
  • Presided over the denial of a medical cannabis dispensary license by the Illinois Department of Professional Regulation, Capital Mgt. v. IDFPR 16CH15228

Banking/Financial Institution

  • Arbitrated dispute between consumer and financial institution under the Electronic Funds Transfer Act
  • At JAMS, mediated dozens of claims between consumers and a nationwide retail bank alleging unauthorized fees for add-on products, unauthorized fees for late payments, and other claims
  • Arbitrated claim against financial institution for failure to turn over title of vehicle once financial obligation was allegedly satisfied

Business Commercial

  • At JAMS, mediated and settled dispute between three business partners after a purchase agreement of a medical waste disposal company revealed nondisclosed business assets
  • Selected as solo arbitrator and subsequently appointed to mediate a dispute between a major Chicagoland developer and their subcontractor.  The mediation-arbitration focused on the development of 17 mixed-use properties in Cook County
  • Arbitrated a dispute for breach of contract involving the enforcement of a settlement agreement resulting from an asset purchase agreement
  • At JAMS, mediated and settled dispute between supplier of defective lubricant for air compressors and manufacture of the compressors alleging breach of contract.
  • At JAMS, mediated and settled dispute between a manufacturer, distributor and third-party bottler concerning a mislabeled product that was eventually recalled by the FDA resulting in personal injury cases.  The case required resolution of the contractual breach, insurance coverage and crafting a path forward to maintain a decades long ongoing business relationship.
  • At JAMS, mediated and settled dispute involving sophisticated parties to an asset purchase agreement of cannabis distribution licenses; involved complex regulatory issues and restructuring of the purchase agreement
  • Presided over, mediated and settled the largest condominium deconversion in Chicago, with an investor purchase price over $100 million; litigated motions to dismiss, summary judgment and motions in limine, before setting a trial date within 120 days of filing to prevent possible exposure for breach of contract by the board; negotiations involved 12 plaintiffs, allegations of self-dealing against individual board members, improper counting of the vote for deconversion and allegations of self-dealing by the investor/purchaser, Pepper v. River City Condominium Assoc. 18CH12423
  • Presided over, mediated and settled allegations of breach of fiduciary duty between LLC members where one LLC member wrongfully sold the property to an individual and collateralized the same property multiple times to third parties, all while the property was subject to environmental violations by various local and state agencies; global settlement involved satisfying the needs of three LLC members with competing interests, five individuals and four corporations as alleged bona fide purchasers and defendants/counter-plaintiffs, a national finance company, and resolving the environmental violations, Rooney v. Daly, et al. 19CH05954
  • Presided over and mediated a breach of contract and breach of fiduciary duty claim by two partners who owned more than 11 fast food restaurants; complex accounting and legal issues were exacerbated by the lack of sophistication of the parties, who primarily did business based on their long-standing personal friendship, which was stifled by allegations of family infidelity, Yusuf v. Lokuandwala 18CH09372
  • Presided over and subsequently selected to mediate complex cross complaints between two major corporations in manufacturing of household products; claims included allegations of breach of contract, specific performance, reformations and failure to meet EPA standards; Multiple mediation sessions required in-depth discussions of more than 100 patents held by the parties and the reformation of the agreement, requiring international law considerations; the parties settled after the last mediation session,  Stepan v. Elevance Renewable Sciences, Inc. 18CH6596 and 18CH7756
  • Presided over a three-week trial involving claims of breach of fiduciary duty, fraud and misappropriation of funds brought by minority members of an LLC against member managers; evidence included complex testimony from accountants, architects and civilians, and required the review of more than 71,000 pages of business records, emails and bank records; trial resulted in disgorgement of funds and interest in the LLC, as well as a second hearing on attorneys’ fees, Tsai v. Karlik I, 2021 IL App (1st) 182200-U; Tsai v. Karlik II, 2022 IL App (1st) 200845-U
  • Mediated a breach of contract, common law fraud, statutory fraud and request to invalidate a noncompetition agreement alleging that defendant epoxy manufacturer violated the stock share purchase agreement; negations involved multiple defendants, including an international bank holding the funds allegedly withheld from the plaintiff, Sacks v. Corro Shield, 2020 IL App (1st) 190760-U

Construction

  • Settled dispute between public garage and condominium association over the repair of deteriorated garage floor membrane and use and ownership of common elements of the building, Fulton Court Condo Assoc. v. Smithfield Properties XXI 20CH6013
  • Presided over and mediated dispute between condo owner’s allegations of private nuisance against developer of another condo unit; mediations and trial involved complex expert testimony concerning flooring and soundproofing: Frost v. DMMD, LLC 16CH15183

Class Action & Mass Tort

  • Presided over a contested class certification hearing of management-level car salesmen employed at 18 dealerships alleging violations under the Illinois Wage Payment and Collection Act for improper deductions; after class certification was affirmed by the appellate court, mediated and settled the class action and presided over the preliminary and final approval, Meir v. Rohrman, 2020 IL App (1st) 192401-U
  • Arbitrated estate claim for asbestos contamination resulting in death due to exposure at 17 construction sites now administered by a trust.

Illinois Biometric Information Privacy Act (BIPA)

  • At JAMS, mediated and settled BIPA claim against Personal Protective Equipment (PPE) manufacturer involving two separate classes
  • Settled BIPA claims for hospital employees against major hospital in Cook County, Francois v. South Shore Hospital Corp. 21CH02564
  • Settled BIPA claims and insurance coverage dispute as global settlement, Scottsdale Insurance Co. v. Mini Storage Maintenance, LLC, et al. 20CH07294; Romero v. Mini Storage Maintenance, LLC 20CH03021
  • Presided over BIPA litigation addressing whether the federal Labor Management Relations Act preempts claims under BIPA: Walton v. Roosevelt University, 2023 IL 128338
  • Presided over BIPA litigation adjudicating whether the court has personal jurisdiction over an out-of-state manufacturer of biometric key access machines and whether they are subject to the act; subsequently presided over the preliminary approval of the settlement of both the employer and the biometric machine manufacturer, Fisher v. HP Property Management, LLC, et al., 2021 IL App (1st) 201372
  • Presided over BIPA litigation addressing whether the Illinois Workman’s Compensation Act preempts a claim under BIPA, Mims v. Freedman Seating Company 18CH09806
  • Presided over BIPA litigation addressing whether an online beauty “try on” application is subject to the Act as facial recognition, Durheim v. Sally Beauty Supply Inc. 22CH09383
  • Presided over BIPA litigation addressing whether an independent contractor sufficiently produced evidence it received state funds thereby exempting it from the Act, Bayeg v. Eden Management 19CH08821
  • Presided over BIPA litigation addressing whether an individual who claims not to be a franchisee of a statewide pizza franchise is subject to the Act, Pournaras v. Beggers Pizza, et al. 21CH00497
  • Presided over preliminary and final approval of class action lawsuits under BIPA of more than 30 cases involving defendants from the following types of businesses:
    • National food chains
    • National food distributors
    • Nursing homes/home health care companies
    • National manufacturing company
    • Senior living facilities
    • National hotel chain
    • Property management companies
    • Pet supply company
    • National staffing company

Civil Rights

Both as a lawyer and judge, Judge Demacopoulos has extensive experience in criminal law and procedure, including allegations of false arrest, police misconduct, false confessions and wrongful convictions. She brings a unique perspective to civil rights cases with her extensive experience in presiding over FOIA cases involving investigative files. 

  • Adjudicated complex high-profile FOIA request for the investigative file of Valerie Percy’s murder in 1966; conducted in camera review of thousands of pages of the police investigation by multiple law enforcement agencies spanning more than 50 years, including complex issues of privacy and balancing the need for transparency, yet maintaining the integrity of the ongoing investigation; upon remand, mediated and settled all FOIA claims and attorneys’ fees issues, Kelly v. Village of Kenilworth, 2019 IL App (1st) 170780
  • Participated in the largest police corruption case involving police misconduct of the Special Operations Section of the Chicago Police Department; prosecution of more than a dozen police officers, sergeants and lieutenants involved the intensive review of thousands of pages of police reports, bank records, phone records and the interview of civilian witnesses; case involved delicate negotiations between prosecutors and criminal defense attorneys, People v. Jerome Finnigan, et al.

Employment Law

  • At JAMS, mediated and settled pre-suit dispute of sexual harassment between high performing executives. Company wished to retain both employees. Settlement consisted of resolving dispute and assisting the company in establishing formal performance reviews and reporting protocol.
  • Arbitrated claim of wrongful termination of an alleged whistleblower by national financial institution.
  • Mediated and settled a breach of noncompete, nonsolicitation agreement against former employee who agreed to the restrictive covenants after the buyout of his worldwide design magazine; negotiations involved the disgorgement of profits from unauthorized side dealings with an employee and other complex issues in the design industry, Rightsize v. Obstfeld 18CH04551
  • Mediated and settled claims for theft of client private information, financial and consulting information, and company trade secrets, as well as for defamation: Fort Dearborn Partners v. Muehling 19CH01597
  • Presided over pretrial maters and mediated allegations of misappropriation of trade secrets, conversion and breach of noncompete against a 45-year high-ranking manager of an international packing company; multiple mediation sessions required the in-camera review of thousands of pages of confidential material, results of forensic audits of computers and expert opinions; parties settled the matter after the final mediation session: Signode Industrial Group v. Rutsky 21CH00314
  • Presided over allegations of wrongful termination of a profit-interest member of an investment advisory firm; litigation centered on complex legal issues involving the securities industry, accounting and the in-camera review of emails and documentation that led to a confidentially negotiated sale of securities by defendant allegedly depriving plaintiff of millions of dollars in profit sharing: Francis v. SpiderRock 20CH00735

Labor

  • At JAMS, mediated and settled decades long legal dispute between a coalition of employers and the Illinois Department of Labor concerning the classification of laborers and alleged violations of the Illinois Prevailing Wage Act.
  • Mediated allegations of violations of Employee Classification Act by owner of bricklaying company under the Illinois Minimum Wage Law and applicable federal law: Administrative District Council 1 of Illinois of the International Union of Bricklayers and Allied Craft Workers v. Brickster Inc. 20CH6707
  • Presided over BIPA litigation addressing whether the federal Labor Management Relations Act preempts claims under BIPA: Walton v. Roosevelt University, 2023 IL 128338

Insurance

  • At JAMS, mediated and settled decades old litigation dispute between life insurance carrier and surviving spouse.
  • Presided over, mediated and settled insurance claim under the false pretense coverage endorsement, Skyline v. Auto Owners 19CH10541
  • Presided over complex insurance coverage matter involving multiple contractors, subcontractors and additional insured involving a major injury occurring during reconstruction on a major highway, Westfield Insurance Co. v. Walsh Construction, et al. 18CH06143
  • Presided over cross-complaints of multiple insureds’ duty to defend for transportation carrier lease of a trailer involved in accident resulting in death, Star Ins. Co. v. All Way Trucking, et al. 15CH 465
  • Presided over duty to pay a $50 million restitution settlement in the civil prosecution of a violation of Medicare/Medicaid fraud, Liberty Insurance Underwriters v. Astellas Pharma US, Inc., and Astellas US Holding, Inc. 19CH14483

Real Property

  • Presided over class certification hearing creating subclasses of tenants of a multi-building apartment complex managed by defendant management company for violating the Residential Landlord and Tenant Ordinance (RLTO); subsequently presided over the preliminary and final approval of settlement, Doaks v. Related Management Co., et al. 19CH08614
  • Presided over preliminary and final approval of RLTO matter for failure to comply with security deposit requirement, Fisher v. East Lake Management Group 17CH10673
  • Presided over hearing overruling an objection to final approval of class settlement: Rovner v. Forest City Residential 15CH10028
  • Settled property claims between neighboring businesses that shared a common wall of an 1800s-era building: Gallardo v. Old National Bank 23CH07749
  • Adjudicated and mediated dispute between a commercial tenant and several successors of the tenant’s original landlord over the responsibility for paying water charges: Medici Gallery and Coffee House v. Pioneer UC V, Inc., 2023 IL App (1st) 220321-U
  • Adjudicated and mediated claim over a 1911 easement and whether encroachments attached to a building violated the easement: Victoria Entertainment v. Phoenix Steps Inc. 16CH10298
  • Presided over claim of unlawful denial of a harbor permit: NPM v. City of Chicago, et al. 21CH04537

Professional Liability

  • At JAMS, mediated and settled dispute between deceased’s estate and large law firm for breach of fiduciary duty alleging misappropriation of funds by a senior partner who advised on estate planning  
  • At JAMS, mediated and settled dispute between attorneys for the recovery of fees in a national class action lawsuit based on an implied oral contract to split fees.
  • At JAMS, mediated pre-suit dispute between investment firm and national law firm alleging legal malpractice and breach of fiduciary duty when firm partner is alleged to have participated in misappropriation of funds.
  • Mediated and settled claims of breach of fiduciary duty and conversion between two highly successful law partners and allegations against a third attorney; negotiations required multiple sessions and involved complex legal, accounting and ethical considerations,  Morrissey v. Wise, et al. 23CH00142

Securities

  • Presided over a claim under §12(a)(1) of the United States Securities Act of 1933, 15 U.S.C. §77l(a)(1), alleging that AbbVie issued new shares of stock without having a registration statement in effect; plaintiff alleged that AbbVie stock he received was issued in exchange for Allergan stock as part of AbbVie’s acquisition of Allergan; the terms of the exchange were held to be fair by the Irish High Court, at which any interested party had a right to attend, either in person or by counsel; plaintiff further alleged that the Irish High Court’s hearing did not satisfy §77c(a)(10) because COVID-19 travel restrictions prevented him and other Allergan shareholders who live in the U.S. from traveling to Ireland to attend the hearing in person, Twigg v. AbbVie 21CH02334 (Affirmed on appeal.) (25 Ill. App. 1st. 221581)
  • Presided over the request for injunctive relief for a claim of improper deprivation of plaintiff’s right to convert pursuant to its convertible note and improper termination of its contractual right of a shareholder agreement to a board seat in a soon-to-be-public company involving financing of more than $40 million: JVC HFT LLC. v. Endotronix, et al., 2018 IL App (1st) 171298-U
  • Mediated cross-claims for the request for specific performance for the sale of penny stocks allegedly valued at $13,000 and the allegation of securities fraud when the actual value was $1.4 million: Godeaux v. Evergreen 21CH01948

Trusts

  • At JAMS, mediated and settled family dispute between cousins involving inherited commercial property
  • At JAMS, mediated and settled years long dispute between siblings and next generation beneficiaries alleging undue influence, forgiven loans, misappropriation of funds by trustee and various other claims.  
  • Settled a long-standing family dispute involving siblings and half siblings alleging breaches of fiduciary duty and fraud over ownership of land subject to conflicting trust instruments: Wafer v. Jones 19CH03584
  • Adjudicated a bank trustee’s request to interpret whether a deceased beneficiary properly exercised his power of appointment over trust assets as provided by the original settlor; litigation involved issues of choice of law and complex cross-motions for summary judgment filed by multiple parties: Bank of America v. Hendrickson, et al.  21CH0779

Honors, Memberships, and Professional Activities

Memberships and Affiliations

  • Member, Dispute Resolution Section, American Bar Association
  • Member, Dispute Resolution Committee, Chicago Bar Association
  • President, Order of Themis, Hellenic Judges Association, 2022-2023
  • Member, Board of Directors, Officer, Hellenic Bar Association of Illinois, 1989–2026
  • Board Member, Illinois Judges Association, 2008–2023
  • Presiding Judge of Nationally Acclaimed, Emmy Award-Winning Mock Trial, National Hellenic Museum
  • Member, Chicago Inns of Court, 2020–2026
  • Certificate in Mediation, Northwestern University School of Professional Training, 2018
  • Planning Committee Member, WE (Women Everywhere Partners In Service, Inc.), 1998–2020
  • Member, Alumni Board, University of Illinois Chicago School of Law, 1997–2013
  • Member, Hellenic American Leadership Council, 2010–2026

Selected Awards and Honors

  • Lifetime Achievement Award, Hellenic Bar Association, 2024
  • Trailblazer Award, Hellenic Bar Association, 2023Liberatum Award, Illinois Judges Association, 2022
  • Mary Hofelt Hooton Award, Women’s Bar Association of Illinois, 2020
  • Honorary Doctor of Laws, University of Illinois Chicago School of Law, 2017
  • Bishop Sheil Award, Illinois State Crime Commission, 2008
  • Distinguished Alumni Award, Alan B. Shepard High School, 2008
  • Special Commendation, Chicago Police Department, 2007
  • Distinguished Service Award, University of Illinois Chicago School of Law, 2006

Background and Education

  • First Assistant State’s Attorney, Cook County State’s Attorney’s Office, 2024–2025
  • Mediator/Arbitrator, JAMS, 2023–2024
  • Judge, Circuit Court of Cook County (Illinois), 2008–2023
    • Chancery Division, 2015–2023
    • Criminal Division, 2008–2015
  • Cook County State’s Attorney’s Office, 1985–2008
    • Supervisor, Felony Trial Unit, Narcotics Prosecution Bureau, 2003–2008
    • Supervisor, Special Grand Jury/Preliminary Hearings, Narcotics Prosecution, 2001–2003
    • Supervisor, Deputy Supervisor, Felony Review Unit, Criminal Prosecution Bureau, 1998–2001
    • Deputy Supervisor, First Municipal District, Criminal Prosecution, 1993–1998
    • Assistant State’s Attorney, Criminal Prosecutions Bureau, 1985–1993
  • Adjunct Professor of Law, Trial Advocacy, University of Illinois Chicago School of Law, 1987–2023
  • U.S. Department of Justice, Bureau of Justice Assistance, 1997–2002
    • Peer Panel Grant Reviewer
    • Program Developer for Violence Against Women’s Office
  • J.D., University of Illinois Chicago School of Law (f/k/a The John Marshall School of Law), 1985
  • B.A., Communications, Loyola University Chicago, 1982

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