Hon. Anna H. Demacopoulos (Ret.) brings over four decades of experience as a judge and attorney to her work as a mediator, arbitrator, and court appointed neutral at JAMS. Judge Demacopoulos was a sought after pre-trial mediator in the Cook County Chancery Division, where she presided over complex litigation.
On the bench, Judge Demacopoulos’ docket included class actions, shareholder derivative actions, employment and labor disputes, insurance coverage, trusts, professional liability, and complex commercial litigation. She regularly handled urgent legal decisions, requiring prompt action under pressure and careful management of matters with significant financial and reputational implications. This experience informs her ability to guide parties to resolution through 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 advising on significant legal and policy matters. Her responsibilities included overseeing significant matters and implementing operational reforms. 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, arbitrator and court appointed neutral who helps parties focus on the core issues and achieve resolution. She works with counsel and clients to reach clear, practical, and durable resolutions in complex disputes.
Representative Matters
Judge Demacopoulos has handled a wide variety of matters as a sitting judge, public sector attorney and as a neutral at JAMS. Matters listed were handled at JAMS unless otherwise indicated.
Administrative Law
- As a sitting judge, mediated matter involving violations of the City of Chicago Ethics Ordinance by an employee of the Civilian Office of Police Accountability.
- As a sitting judge, mediated matter involving revocation of a liquor license.
- As a sitting judge, handled matter involving revocation of a gaming license where licensee alleged violation of due process and Open Meetings Act.
- As a sitting judge, handled an applicant's constitutional challenges to the Conditional Adult Use Dispensing Organization Licenses under the Illinois Cannabis Regulation and Tax Act (CRTA).
- As a sitting judge, handled the denial of a medical cannabis dispensary license by the Illinois Department of Professional Regulation.
Banking/Financial Institution
- Arbitrated to award dispute between consumer and financial institution under the Electronic Funds Transfer Act.
- Mediated dozens of claims between consumers and a nationwide retail bank alleging unauthorized fees and other claims.
- Arbitrated claim against financial institution for failure to turn over title of vehicle once financial obligation has been allegedly satisfied.
Business Commercial
- Mediated dispute of alleged improper invoicing pursuant to a master service agreement between intermodal service facility and terminal operator charged with providing equipment, labor and technology systems.
- Mediated 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.
- Mediated dispute between supplier of defective lubricant for air compressors and manufacturer of the compressors alleging breach of contract.
- Mediated dispute involving sophisticated parties to an asset purchase agreement of cannabis distribution licenses; involved complex regulatory issues and restructuring of the purchase agreement.
- As a sitting judge, mediated the largest condominium deconversion in Chicago, with an investor purchase price over $100 million. Claims involved 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.
- As a sitting judge, mediated 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.
- As a sitting judge, mediated a breach of contract and breach of fiduciary duty claim by two partners who owned more than 11 fast food restaurants. Parties primarily did business based on their long-standing personal friendship, which was stifled by allegations of family infidelity.
- As a sitting judge, mediated 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.
- As a sitting judge, handled matter involving claims of breach of fiduciary duty, fraud and misappropriation of funds brought by minority members of an LLC against member managers.
- As a sitting judge, 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.
Construction
- As a sitting judge, mediated 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.
- As a sitting judge, 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.
Class Action/Mass Tort
- As a sitting judge, handled 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.
- 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)
- Mediated BIPA claim against Personal Protective Equipment (PPE) manufacturer involving two separate classes.
- As a sitting judge, mediated BIPA claims for hospital employees against major hospital in Cook County.
- As a sitting judge, mediated BIPA claims and insurance coverage dispute as global settlement.
- As a sitting judge, handled BIPA litigation addressing whether the federal Labor Management Relations Act preempts claims under BIPA.
- As a sitting judge, handled 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.
- As a sitting judge, handled BIPA litigation addressing whether the Illinois Workman’s Compensation Act preempts a claim under BIPA.
- As a sitting judge, handled BIPA litigation addressing whether an online beauty “try on” application is subject to the Act as facial recognition.
- As a sitting judge, handled BIPA litigation addressing whether an independent contractor sufficiently produced evidence it received state funds thereby exempting it from the Act.
- As a sitting judge, handled BIPA litigation addressing whether an individual who claims not to be a franchisee of a statewide pizza franchise is subject to the Act.
- As a sitting judge, handled more than 30 preliminary and final BIPA class certifications 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
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.
- As a sitting judge, 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 investigative files from law enforcement agencies spanning more than 50 years. The files presented complex privacy issues set against the need for transparency and an ability to maintain the integrity of ongoing investigation. Upon remand, mediated and settled all FOIA claims and attorneys’ fees issues.
- As a prosecutor, 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. The case involved delicate negotiations between prosecutors and criminal defense attorneys.
Employment Law
- Mediated 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.
- As a sitting judge, mediated a breach of non-compete, non-solicitation 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.
- As a sitting judge, mediated claims for theft of client private information, financial and consulting information, and company trade secrets, as well as for defamation.
- As a sitting judge, handled pre-trial matters and mediated allegations of misappropriation of trade secrets, conversion and breach of noncompete against a 45-year tenured, 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.
- As a judge, handled matter involving 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.
Labor
- Mediated 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.
- As a judge, handled BIPA litigation addressing whether the federal Labor Management Relations Act preempts claims under BIPA.
Insurance
- Mediated dispute between life insurance carrier and surviving spouse where insurance carrier claimed cause of death was suicide, but litigation resulted in adverse finding.
- Mediated dispute between general contractor, subcontractor and workman’s compensation insurance carrier because of a construction site personal injury.
- As a sitting judge, mediated insurance claim under the false pretense coverage endorsement.
- As a judge, handled complex insurance coverage matter involving multiple contractors, subcontractors and additional insured involving a major injury occurring during reconstruction on a major highway.
- As a judge, handled matter involving cross-complaints of multiple insureds’ duty to defend for transportation carrier lease of a trailer involved in accident resulting in death.
- As a judge, handled matter involving duty to pay a $50 million restitution settlement in the civil prosecution of a violation of Medicare/Medicaid fraud.
Professional Liability
- Mediated 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.
- Mediated dispute between attorneys for the recovery of fees in a national class action lawsuit based on an implied oral contract to split fees.
- 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 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. Dispute involved issues related to alleged contractual breach, insurance coverage and the development of a framework to facilitate the continuation of a longstanding business relationship.
- Mediated 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.
Real Property
- As a judge, handled matter involving 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).
- As a judge, handled matter involving preliminary and final approval of RLTO matter for failure to comply with security deposit requirement.
- As a judge, handled matter involving hearing overruling an objection to final approval of class settlement.
- As a judge, mediated matter involving breach of easement and trespass between neighboring restaurant businesses that shared a common wall of an 1800s-era building.
- As a judge, handled and mediated dispute between a commercial tenant and several successors of the tenant’s original landlord over the responsibility for paying water charges.
- As a judge, handled and mediated claim over a 1911 easement and whether encroachments attached to a building violated the easement.
- As a judge, handled matter involving claim of unlawful denial of a harbor permit.
Securities
- As a judge, handled complex securities dispute arising from AbbVie’s acquisition of Allergan, involving allegations related to share issuance and the application of a registration exemption under the Securities Act of 1933.
- As a judge, handled matter involving 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.
- As a judge, handled mediation of matter involving crossclaims 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.
Trusts
- Mediated a family dispute between cousins involving inherited commercial property.
- Mediated dispute between siblings and next generation beneficiaries alleging undue influence, forgiven loans, misappropriation of funds by trustee and various other claims.
- As a judge, handled and mediated matter involving 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.
- As a judge, handled matter involving 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.
Honors, Memberships, and Professional Activities
Memberships and Affiliations
- Member, Dispute Resolution Committee, Chicago Bar Association
- Member, Dispute Resolution Section, American Bar Association
- President, Order of Themis, Hellenic Judges Association, 2022-2023
- Member, Board of Directors, Officer, Hellenic Bar Association of Illinois, 1989–2026
- Member, Board Member, Illinois Judges Association, 2008–2026
- Presiding Judge of Nationally Acclaimed, Emmy Award-Winning Mock Trial, National Hellenic Museum
- Member, Chicago Inns of Court, 2020–present
- 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
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Member, Hellenic American Leadership Council, 2010–2026
Selected Awards and Honors
- Lifetime Achievement Award, Hellenic Bar Association, 2024
- Trailblazer Award, Hellenic Bar Association, 2023 Liberatum 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
- Neutral, JAMS, 2025 to present
- First Assistant State’s Attorney, Cook County State’s Attorney’s Office, 2024–2025
- Neutral, 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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