Kaitlin Elizabeth O'Brien — professional portrait

Kaitlin Elizabeth O'Brien · Senior Associate · Lippes Mathias LLP

Rochester · New York · Counsel at Law

Kaitlin Elizabeth O'Brien, J.D.

Seven years after the crimson and purple regalia on the steps of Marsh Chapel, the J.D. has been put thoroughly to work. Kaitlin is now a Senior Associate in the Litigation Practice Team at Lippes Mathias LLP, based in the firm's Rochester office, where she represents clients in complex commercial disputes across New York State.

Admitted to practice in both New York and Massachusetts, she moves easily between state court litigation, hospital-side guardianship proceedings, and the kind of document-heavy commercial cases where the answer lives three layers down in an assignment clause nobody read carefully enough.

In September 2024 she was named an "Up and Coming Lawyer" by the Rochester Business Journal in its annual Attorneys of the Year awards — a recognition that the people practicing alongside her already saw coming.

Seven Years at the Bar

A Career in Progress

Jan 2025 — Present

Senior Associate

Lippes Mathias LLP · Rochester, New York

Promoted to Senior Associate in January 2025 — one of eleven attorneys elevated across the firm's footprint that cycle. Continues her commercial litigation docket and leads the firm's internal social committee.

Apr 2024 — Jan 2025

Associate

Lippes Mathias LLP · Rochester, New York

Joined Lippes Mathias with fellow Rochester litigator Kelly S. Foss in a notable lateral move, bringing a commercial litigation practice focused on life settlements, contract disputes, and health care guardianship matters.

Jun 2021 — Apr 2024

Associate

Harris Beach PLLC · Rochester, New York

Nearly three years at one of upstate New York's storied regional firms, broadening the commercial litigation practice and building the network of judges, clerks, and opposing counsel that defines a Rochester attorney's career.

Sep 2018 — May 2021

Litigation Associate

Cain Hibbard & Myers PC · Pittsfield, Massachusetts

First post-J.D. position — nearly three years learning the craft of litigation at a Berkshires firm with deep roots in Western Massachusetts. The groundwork: motions, depositions, courtroom hours, and the thousand small disciplines of actually practicing law.

Aug 2017 — May 2018

3:03 Student Prosecutor

BU Law Criminal Clinic · Quincy District Court

Under Massachusetts Supreme Judicial Court Rule 3:03, independently prosecuted drug and motor vehicle offenses — real cases, real defendants, real consequences, with a supervising ADA but on her own two feet in the courtroom.

May 2017 — Aug 2017

Law Clerk

Swartz & Swartz P.C. · Boston, Massachusetts

Summer clerkship at a Boston plaintiff-side trial firm known for product liability and personal injury litigation. Drafting motions, researching case law, and learning how a working courtroom practice runs from the inside.

Practice & Pursuits

The Work

Complex Commercial Disputes

The bread and butter of a commercial litigator's docket: contract disputes, non-compete enforcement, business torts, disagreements between parties that were, at some prior and more optimistic moment, supposed to be working together. Kaitlin has handled these in New York state court across a range of industries, preparing complaints and motions, conducting records review, and — in the cases that don't need a jury — negotiating settlements that let everyone move on.

Life Settlements & UCC Article 8

A specialty corner of the commercial world: disputes over who owns what slice of a life insurance policy's proceeds, often involving undisclosed collateral assignments, interpleader actions, and the protected-purchaser and securities-entitlement defenses buried in Article 8 of the Uniform Commercial Code. The sort of case where the legal theory matters as much as the facts.

Health Care & Guardianship

Kaitlin represents hospitals, health care providers, and skilled nursing facilities in Article 81 Mental Hygiene Law proceedings — the New York statute governing guardianships for adults who can no longer manage their own affairs. These are delicate cases, often contested, almost always involving a family that is grieving something even when nobody is dying. Good counsel here is more than good lawyering.

Estates, Employment, & Administrative Challenges

A rounded commercial litigation practice also touches estate administration disputes, employment claims, and challenges to administrative agency decisions — the moments when the state's machinery gets something wrong and someone needs to push back through the proper channels. Kaitlin handles these alongside her primary commercial docket.

Research & Appellate Support

As a research assistant at BU Law, Kaitlin annotated legislative history to support an Amicus brief filed with the United States Supreme Court. She also served as a law clerk for the Criminal Justice Institute at Harvard Law School and as a Legal Writing Fellow at BU Law — the sort of preparation that makes a young attorney's first appellate brief feel like familiar terrain.

Recognition & Associations

Named "Up and Coming Lawyer" in the Rochester Business Journal's 2024 Attorneys of the Year Awards. Inaugural class (2023) of the Monroe County Bar Association Leadership Academy. Member of the New York State Bar Association and the Greater Rochester Association of Women Attorneys.

Of Counsel

Representative Matters

Life Settlement Interpleader

Counsel to a life settlement investor in a dispute involving multiple claimants to policy proceeds under an undisclosed collateral assignment, and a verification of coverage that warranted the policy was not assigned. The interpleader involved claims for breach of contract, estoppel, negligent misrepresentation, and protected-purchaser and securities-entitlement defenses under Article 8 of the UCC.

Commercial Landlord v. Repudiating Tenant

Counsel to a commercial landlord in a dispute with a commercial tenant that anticipatorily repudiated its lease. Successfully moved for summary judgment on claims of anticipatory repudiation and declaratory judgment.

Article 81 Guardianship Proceedings

Counsel to hospitals and skilled nursing facilities in complex Article 81 Mental Hygiene Law proceedings, including contested guardianship matters where the interests of patient, family, and institution require careful legal navigation.

At Home in
Rochester

She lives in Rochester, New York with her partner Tyler McNamara and her standard poodle Lincoln — a breed she comes by honestly, having grown up with the same in the family house on Chautauqua Lake.

Rochester is a good city for a lawyer. The federal courthouse on State Street, the Hall of Justice a few blocks away, the historic downtown, the Genesee River cutting the city in two. It is serious without being ponderous, and it has preserved an architectural character that Buffalo and Syracuse have, in places, let slip.

The Essentials

City · Rochester, New York
Partner · Tyler McNamara
Companion · Lincoln, standard poodle
Firm · Lippes Mathias LLP
Office · Rochester
Bars · New York & Massachusetts

A Father's Note

The Long View

"A father's job, in the best version of the story, is to be present at these moments — not as the protagonist, but as a witness."

There is a version of this story where the 2018 BU Law graduation is the end of the arc — the robes, the ceremony, the photograph on the steps of Marsh Chapel, and then whatever comes next is off camera. But the interesting part of any commencement is precisely what it says on the tin: this is a beginning. The degree is the ticket to the arena, not the trophy at the end of it.

Seven years on, the ticket has been used. Kaitlin has built an actual practice — a docket, a reputation among the judges and clerks of the Fourth Department, clients who call her because they have been told she knows what she is doing, opposing counsel who have learned to prepare carefully for her filings. She has moved from a first-job firm in the Berkshires to a major regional practice in Rochester, then laterally to Lippes Mathias, and then up. This is not a credential. It is a career.

Litigation is one of the harder ways to make a living as a lawyer. The hours are unpredictable, the adversarial posture is wearing, and the cases that matter most are rarely the ones that resolve cleanly. It takes a particular kind of mind to enjoy the work — a tolerance for ambiguity, a gift for reading a statute and finding the seam, a willingness to argue a position in the morning and spot its weakness by lunch. Kaitlin has always had some version of that mind. Law school merely handed it a vocabulary.

The "Up and Coming Lawyer" recognition from the Rochester Business Journal is the kind of honor that looks, at first glance, like professional politeness — a nod from the business community to a younger attorney on the way up. It isn't. Rochester is a small legal market; the lawyers who vote on these things have actually seen the work. When they pick someone, they are choosing from among people they have watched in court, across the table, and at the bar association dinners where the real conversations happen. It means something.

There is a standard poodle in Rochester named Lincoln, a partner named Tyler, a good place to live, a standing reservation at a favorite restaurant, and a career that is now fully her own. A father cannot claim credit for any of it. The best he can do is notice, carefully and in full, what has been built.