
Business Law | Litigation | Estates & Trusts | Commercial Transactions
Liff, Walsh & Simmons is a full-service business law firm located in Annapolis, Maryland. We serve the legal needs of small businesses and privately held companies, their owners, and operators in the mid-Atlantic region.
Business Law | Litigation
Estates & Trusts | Commercial Transactions
Liff, Walsh & Simmons is a full-service business law firm located in Annapolis, Maryland. We serve the legal needs of small businesses and privately held companies, their owners, and operators in the mid-Atlantic region.
SCHEDULE A CONSULTATIONATTORNEYS
Our Committed Team
At Liff, Walsh & Simmons, our attorneys are trusted advisors who understand both the law and the realities our clients face. We take a collaborative, solutions‑driven approach to help clients navigate complex legal matters with confidence.

James R. "Jay" Walsh
Managing Partner
Banking & Finance Law | Business Contracts, Counseling & Transactional Law | Real Estate Law

Thomas W. Simmons
Partner
Banking & Finance Law | Business Contracts, Counseling & Transactional Law | Real Estate Law

Jonathan W. McGowan
Partner
Banking & Finance Law | Business Counseling, Contracts & Transactions Law | Estate Planning & Administration Law | Real Estate Law | Labor & Employment Law

Kelly E. Callahan
Partner
Banking & Finance Law | Business Counseling, Contracts & Transactions Law | Real Estate Law

Andre S. Habib
Associate
Banking & Finance Law | Business Counseling, Contracts & Transactions Law | Real Estate Law

Kathleen S. Millrood
Associate
Banking & Finance Law | Business Counseling, Contracts & Transactions Law | Real Estate Law

Peter M. Shenouda
Associate
Banking & Finance Law | Business Counseling, Contracts & Transactions Law | Real Estate Law
OUR TEAM
Attorneys

James R. "Jay" Walsh
Managing Partner
Banking & Finance Law | Business Contracts, Counseling & Transactional Law | Real Estate Law

Thomas W. Simmons
Partner
Banking & Finance Law | Business Contracts, Counseling & Transactional Law | Real Estate Law

Jonathan W. McGowan
Partner
Banking & Finance Law | Business Counseling, Contracts & Transactions Law | Estate Planning & Administration Law | Real Estate Law | Labor & Employment Law

Kelly E. Callahan
Partner
Banking & Finance Law | Business Counseling, Contracts & Transactions Law | Real Estate Law

Andre S. Habib
Associate
Banking & Finance Law | Business Counseling, Contracts & Transactions Law | Real Estate Law

Kathleen S. Millrood
Associate
Banking & Finance Law | Business Counseling, Contracts & Transactions Law | Real Estate Law

Peter M. Shenouda
Associate
Banking & Finance Law | Business Counseling, Contracts & Transactions Law | Real Estate Law



PUBLICATIONS
News & Articles
Expert Authors
Thought leadership from our attorneys, offering clear insight on legal issues that impact businesses, employers, and families.
Important Updates
Firm hirings, recognitions, and timely announcements shaping what matters to our clients and community.
Liff, Walsh & Simmons and Eagle Title Expand Community Impact Through Q2 “Denim for a Cause” Giving Initiative
Annapolis, MD (July 2026) -- Liff, Walsh & Simmons, together with Eagle Title, continues to make an impact across the community through Denim for a Cause, a firmwide giving initiative…
Personal Guaranties Explained: What Business Owners Should Know Before SigningPersonal Guaranties Explained: What Business Owners Should Know Before Signing
Forming a limited liability entity can help create separation between a business owner’s personal assets and the company’s liabilities and obligations. However, when you are operating and growing your business,…
Do I Have an Estate Planning Problem? | Choosing a FiduciaryDo I Have an Estate Planning Problem? | Choosing a Fiduciary
"I’m Not Sure Who to Trust to Execute My Estate Planning Wishes. Do I Have an Estate Planning Problem?" The short answer is no. If the thought of selecting…
2026 Best Places to Work Honoree | Baltimore Business Journal2026 Best Places to Work Honoree | Baltimore Business Journal
Liff, Walsh & Simmons / Eagle Title Named a 2026 Best Places to Work Honoree by the Baltimore Business Journal Annapolis, MD (June 26, 2026) -- Liff, Walsh &…
”"They have proven themselves to be versatile, responsive, and competent in all areas of the law. Regardless of the size and scope of the issue, they have someone on their team that specializes in that area of the law and swiftly handles the issue."
”"I had an excellent experience receiving estate advice and planning guidance. Everything was explained clearly and thoughtfully, which made a complex process feel much more manageable."
”"Jay and his team at Liff, Walsh & Simmons truly understand what it means to delineate between legal advice and business advice and their business insights have been invaluable. They have stepped up for me in ways that have been truly game changing for my business."
”"There are a lot of attorneys out there who understand the law but very few who can put themselves in the position of the business owner and give recommendations as a partner."
”"Greg was terrific—he carefully listened to us, our concerns, and questions. He is grounded, friendly and clearly, very well educated in his field. He took time to explain the “language” and guided us through the entire and on-going process."
”"Attorney Jesse Walsh was a strong advocate and provided an open line of communication, as well as much appreciated guidance. I highly recommend the law firm of Liff, Walsh, & Simmons."
PUBLICATIONS
News & Articles
Liff, Walsh & Simmons and Eagle Title Expand Community Impact Through Q2 “Denim for a Cause” Giving InitiativeLiff, Walsh & Simmons and Eagle Title Expand Community Impact Through Q2 “Denim for a Cause” Giving Initiative
Annapolis, MD (July 2026) -- Liff, Walsh & Simmons, together with Eagle Title, continues to make an impact across the community through Denim for a Cause, a firmwide giving initiative…
Personal Guaranties Explained: What Business Owners Should Know Before SigningPersonal Guaranties Explained: What Business Owners Should Know Before Signing
Forming a limited liability entity can help create separation between a business owner’s personal assets and the company’s liabilities and obligations. However, when you are operating and growing your business,…
TESTIMONIALS
Why Use Liff, Walsh & Simmons?
”"They have proven themselves to be versatile, responsive, and competent in all areas of the law. Regardless of the size and scope of the issue, they have someone on their team that specializes in that area of the law and swiftly handles the issue."
”"I had an excellent experience receiving estate advice and planning guidance. Everything was explained clearly and thoughtfully, which made a complex process feel much more manageable."
”"Jay and his team at Liff, Walsh & Simmons truly understand what it means to delineate between legal advice and business advice and their business insights have been invaluable. They have stepped up for me in ways that have been truly game changing for my business."
”"There are a lot of attorneys out there who understand the law but very few who can put themselves in the position of the business owner and give recommendations as a partner."
”"Greg was terrific—he carefully listened to us, our concerns, and questions. He is grounded, friendly and clearly, very well educated in his field. He took time to explain the “language” and guided us through the entire and on-going process."
”"Attorney Jesse Walsh was a strong advocate and provided an open line of communication, as well as much appreciated guidance. I highly recommend the law firm of Liff, Walsh, & Simmons."













