Overview

Madeline Hailer is a business litigation associate based in Henderson Franklin’s Naples office, where she assists attorneys in the representation of clients in commercial disputes and civil litigation matters. With a strong background in legal research and writing, Madeline contributes to case development, legal drafting, and litigation strategy with attention to detail and a thoughtful approach.

Prior to joining the firm, Madeline completed two federal judicial clerkships at the U.S. District Court for the District of Oregon. She served under Chief U.S. District Judge Michael McShane and Magistrate Judge Mark Clarke, gaining firsthand insight into federal procedures and judicial reasoning. Her responsibilities included drafting opinions, managing active dockets, preparing judges for hearings, and mentoring legal externs.

Madeline earned her J.D. from the University of Oregon School of Law, where she served on the Executive Board of the Oregon Law Review, worked as a tutor in the nation’s top-ranked Legal Research and Writing Program, and received multiple academic awards for writing and leadership. She also interned with a Portland-based law firm and the Legal Aid Low-Income Taxpayer Clinic, further developing her skills in administrative law and client service.

Madeline holds a Bachelor of Arts in Communications and International Studies from the University of Wisconsin–Madison, where she first cultivated her interest in legal systems and advocacy.

Originally from Kenosha, Wisconsin, Madeline now resides in Naples with her partner, Will, and their dog, Eleanor. Outside the office, she enjoys running, plant-based cooking, historical fiction and traveling.

Professional & Civic Involvement

Madeline is a member of The Florida Bar and the Oregon State Bar. She is actively building professional connections in Southwest Florida and looks forward to engaging in local and pro bono service initiatives.