
Hailey Oestreicher
Attorney Hailey Oestreicher represents insurers, businesses, correctional facilities, healthcare providers, and other clients in civil litigation throughout Montana. Her practice focuses on civil defense, insurance defense, and medical malpractice defense, with an emphasis on careful case analysis, strategic preparation, and clear advocacy.
Hailey brings an especially valuable perspective to litigation from her experience working inside both Montana’s highest state court and the federal trial court system. That background informs how she evaluates legal issues, develops arguments, and prepares cases with an eye toward both the immediate dispute and the issues that may matter later in the litigation.
A native of Roundup and fifth-generation Montanan, Hailey also brings a strong connection to the businesses, professionals, and communities she serves.
Civil Defense Litigation
Hailey handles a broad range of civil defense matters involving businesses, contractors, correctional facilities, and other institutional clients. Her work includes third-party liability claims and other disputes where the factual record, contractual relationships, and allocation of responsibility can become central issues.
She is particularly drawn to the problem-solving side of litigation: sorting through competing accounts, identifying the legal and factual issues that will drive the case, and building a compelling defense around the evidence that matters most. That process allows her to approach each matter with a clear understanding of both the immediate litigation strategy and the client’s broader interests.
Insurance Defense
Hailey represents insurers and insureds in civil liability matters involving a variety of claims and industries. She works closely with clients to assess exposure, evaluate the factual and legal issues presented, and develop a defense strategy tailored to the circumstances of the case.
Her experience clerking at both the trial and appellate levels gives her insight into how courts analyze legal arguments, evaluate the evidentiary record, and address issues that may later become the subject of appellate review. She draws on that perspective when researching complex issues, drafting motions and briefs, and preparing cases for resolution or litigation.
Medical Malpractice Defense
Hailey also represents physicians, clinics, and healthcare institutions facing medical malpractice claims. These cases can involve more than financial exposure. Professional reputation, relationships with patients and colleagues, and the demands of defending a complex claim can all weigh heavily on healthcare professionals.
Hailey approaches medical malpractice matters with an understanding of both the legal and personal concerns involved. She works to expeditiously develop a thorough factual record, analyze the medical and legal issues at the center of the claim, and provide clients with clear guidance throughout the litigation process.
Hailey is a fifth-generation Montanan who grew up in Roundup and was the first in her family to attend college and law school. Her ranching background and small-town upbringing helped shape her practical approach to problem-solving, strong work ethic, and commitment to the communities she serves.
While in law school, Hailey served on the Hamline Law Review, earned a Certificate in Dispute Resolution Theory and Practice, and was selected as both a Blackstone Fellow through Alliance Defending Freedom and a Lex Legal Fellow. Her law review article, The Most Substantial Factor: Analysis of Ambiguous Causation in STAUB as Trustee of Weeks the Myrtle Lake Resort, LLC, was published in Volume 49 of the Mitchell Hamline Law Review.
Outside the office, Hailey is a mother of three and an avid gardener. She and her husband enjoy camping and exploring Montana’s breathtaking outdoors.
- D., summa cum laude, Mitchell Hamline School of Law
- Certificate in Dispute Resolution Theory and Practice
- A. (Political Science and International Relations), Carroll College
- Siena Italian Studies
- Montana (All state courts)
- United States District Court for the District of Montana
- Hamline Law Review, Former Member
- Former Blackstone Fellow, Alliance Defending Freedom
- Former Lex Legal Fellow
- Graduated summa cum laude, Mitchell Hamline School of Law
- Author, The Most Substantial Factor: Analysis of Ambiguous Causation in STAUB as Trustee of Weeks the Myrtle Lake Resort, LLC, 49 Mitchell Hamline Law Review 512 (2023)























