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  1. Professionals

Bailey Brandon

Partner

Chicago

+1 312-558-7963

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  • Overview
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Bailey is a complex commercial litigator who represents companies across a broad spectrum of industries in high-stakes disputes. She has substantial experience in state and federal courts nationwide, bringing a practical, business-focused approach to every matter. Drawing on her deep understanding of her clients’ legal and commercial priorities, she delivers efficient, effective advocacy tailored to the demands of each case.

Bailey handles all phases of litigation and is a zealous advocate from pre-suit strategy through trial. Her practice includes dispositive motion briefing, managing extensive and often contentious fact and expert discovery, and preparing cases for alternative dispute resolution and trial. She is adept at coordinating multi-party and multi-jurisdictional matters and navigating the procedural and strategic complexities that accompany them.

In addition to general commercial disputes, Bailey has defended class actions, mass tort matters, securities litigation, and antitrust cases. She also regularly advises clients on responding to third-party subpoenas and discovery requests, ensuring compliance while safeguarding sensitive business information.

Key Matters

Bailey’s notable past engagements include:

  • Dismissal of US$450M investor class actions. Obtained dismissal of breach of contract and common law tort claims against a major financial services company in multi-party, multi-jurisdictional investor class actions seeking approximately US$450M.
  • Consumer fraud and antitrust claims dismissed at the pleadings stage. Secured dismissal of claims under the Illinois Uniform Deceptive Trade Practices Act and federal antitrust laws against a professional specialty board in the Northern District of Illinois on a motion to dismiss.
  • Defeated class certification in billion-dollar shareholder litigation. Prevented certification of a putative class in a shareholder action arising from a transaction involving a medical device and health care products company, where claimed damages exceeded US$1B.
  • Trial victory defeating injunctive relief in complex business tort case. Represented a global investment manager through trial against tortious interference, negligent misrepresentation, and state antitrust claims; the court denied the plaintiffs’ request for a permanent injunction.
  • Favorable damages verdict for Fortune 500 aerospace client. Achieved a favorable damages verdict following trial on behalf of a Fortune 500 company in mass-tort case where liability was stipulated to.

  • The Best Lawyers: Ones to Watch®in America—Recognized for Mass Tort Litigation and Class Actions (2025-2026) - Defendants, Commercial Litigation (2026), and Product Liability Litigation - Defendants (2026)

Bailey is also active in the firm’s pro bono program, representing individuals seeking asylum, those with previous convictions seeking Certificates of Good Conduct to aid in their employment search, and individuals seeking protection orders. She also regularly serves as a volunteer at the Legal Aid Chicago Clinic, assisting clients with a variety of legal issues. Prior to joining Winston, Bailey served as a Public Interest Law Initiative Graduate Fellow with the Loyola Community Law Clinic. She worked as a Guardian ad litem for children of low income families to ensure they were in safe and caring homes.

While in law school, Bailey was a member of the Loyola Law Journal and the American Lawyer’s Association moot court team. She was also a fellow in Loyola’s Institute for Consumer Antitrust Studies and served as a volunteer for the American Bar Association monitoring and writing about state antitrust and consumer law developments.

Capabilities

Commercial Litigation & Disputes
Financial Services Litigation
Class Actions & Group Litigation
Litigation/Trials
Securities, M&A & Corporate Governance Litigation
Antitrust/Competition
Insurance Litigation

Key Matters

Bailey’s notable past engagements include:

  • Dismissal of US$450M investor class actions. Obtained dismissal of breach of contract and common law tort claims against a major financial services company in multi-party, multi-jurisdictional investor class actions seeking approximately US$450M.
  • Consumer fraud and antitrust claims dismissed at the pleadings stage. Secured dismissal of claims under the Illinois Uniform Deceptive Trade Practices Act and federal antitrust laws against a professional specialty board in the Northern District of Illinois on a motion to dismiss.
  • Defeated class certification in billion-dollar shareholder litigation. Prevented certification of a putative class in a shareholder action arising from a transaction involving a medical device and health care products company, where claimed damages exceeded US$1B.
  • Trial victory defeating injunctive relief in complex business tort case. Represented a global investment manager through trial against tortious interference, negligent misrepresentation, and state antitrust claims; the court denied the plaintiffs’ request for a permanent injunction.
  • Favorable damages verdict for Fortune 500 aerospace client. Achieved a favorable damages verdict following trial on behalf of a Fortune 500 company in mass-tort case where liability was stipulated to.

Credentials

Education

Bailey received a J.D., magna cum laude, from Loyola University Chicago School of Law in 2017, and her B.S., summa cum laude, in Law and Economics from Central Michigan University in 2013.

    Admissions
    • Illinois

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    Capabilities

    Commercial Litigation & Disputes
    Financial Services Litigation
    Class Actions & Group Litigation
    Litigation/Trials
    Securities, M&A & Corporate Governance Litigation
    Antitrust/Competition
    Insurance Litigation
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