Michelle Caiola, a Partner at Phillips & Associates, PLLC, is a New York employment lawyer and civil rights litigator who exclusively represents employees and survivors in workplace sexual harassment, sexual assault, pregnancy discrimination, sex and gender discrimination, disability discrimination, and other employment discrimination matters. Earlier in her career, Caiola litigated employment discrimination cases for the U.S. Equal Employment Opportunity Commission (EEOC), where she litigated individual, class, and systemic discrimination cases.
At Phillips & Associates, Caiola handles high-stakes employment and sexual assault litigation involving executives, financial institutions, technology and media companies, medical professionals, law firms, and public figures. She currently represents former model Crystal McKinney in federal litigation in the Southern District of New York alleging sexual assault by Sean Combs and Harvey Weinstein. Caiola has also handled pregnancy discrimination and compensation litigation involving RBC Capital Markets. She has negotiated millions of dollars in settlements for clients through pre-suit negotiations, mediation, and litigation. Caiola is also counsel of record in Faruque v. JPMorgan Chase, No. 1:24-cv-05734, in the Eastern District of New York, where the court denied the employer's motion to compel arbitration under the Ending Forced Arbitration Act.
At the EEOC, Caiola litigated class and systemic cases involving sexual harassment and sex, race, national origin, age, and disability discrimination. She led a high-profile glass-ceiling sex discrimination lawsuit against Morgan Stanley that settled for $54 million. She also played a key role in a major sexual harassment case against Mitsubishi that settled for $34 million and a class-wide age discrimination case against a major retailer that settled for $3.5 million. Caiola received the EEOC Chair’s Organizational Award, the agency’s highest honor, three times.
Lawdragon Honors
| Honor | Year | Practice |
|---|---|---|
| The 2026 Lawdragon 500 Leading Civil Rights & Plaintiff Employment Lawyers | 2026 | Sexual Abuse, Harassment, Pregnancy Discrimination |
Caiola later oversaw legal departments at Legal Momentum and Equal Rights Advocates, two women’s rights organizations, where she focused on pregnancy and sex discrimination litigation involving law professors, service workers, police officers, firefighters, shipyard workers, tradeswomen, and women in other traditionally male-dominated occupations. She has been a strong advocate for workplace pregnancy accommodations and job protections related to domestic violence.
As Managing Director of Disability Rights Advocates, Caiola obtained court victories and negotiated settlements addressing disability access and civil rights.
As a long-standing workplace advocate, Caiola has testified at government hearings and presented at employment discrimination conferences. She co-authored employment discrimination amicus briefs filed with the U.S. Supreme Court in Mach Mining, LLC v. Equal Employment Opportunity Commission, addressing EEOC enforcement, and Young v. United Parcel Service, Inc., supporting workplace pregnancy accommodations.
Caiola attended Washington University School of Law in St. Louis and received her J.D. with distinction from the University of Iowa College of Law. She earned her undergraduate degree from Kent State University. Caiola is admitted in New York and Missouri and before federal courts including the Southern and Eastern Districts of New York, the U.S. Courts of Appeals for the Second and Ninth Circuits, and the Supreme Court of the United States. She is a member of the National Employment Lawyers Association, New York State Bar Association, New York City Bar Association, and New York State Academy of Trial Lawyers.