Matthew W. O'Toole

Matthew O’Toole is a member of the firm’s General Commercial group where he focuses on estate planning, trusts and estates administration, and business succession planning. Prior to joining Gentry Locke, he worked at a boutique law firm in Richmond that specialized in all facets of trust and estate planning, administration and trustee services. Before practicing law, Matthew worked in private wealth management at SunTrust Bank, as a Vice President of the Closely Held Business group.

Matthew earned his J.D. from the University of Richmond School of Law and his B.A. from James Madison University. He is a proud Richmond native and remains deeply connected to the area he calls home.

A quick handshake

•You worked in broadcasting before deciding to go to law school. What inspired you to make that career change?

Watching and covering sports has always been a passion of mine, but the further along I got in the industry during my short career, the more I realized I preferred to be a fan and a spectator and enjoy the games. As I got older, I also realized I wanted to be closer to home with my friends and family, and knew there would be fewer opportunities in sports broadcasting in this market. Studying law was something that always intrigued me growing up, so I decided to pivot and pursue law school.

•We’d love to hear the story behind you catching a tennis ball from Serena Williams.

U.S Open 2019, a good friend and I went to opening day and night at Ashe Stadium. We had great seats on Ashe to see Serena play Maria Sharapova. She beat Maria pretty soundly, 6-1 6-1. After the match, the winner hits a few tennis balls into the crowd. I was about to go back to the concourse and grab merchandise in between the matches when my friend told me to hang tight as Serena is known to hit the tennis balls to the lower sections as opposed to the upper sections. Sure enough, he was right. She hit the ball to our section, I extend my arms, and the rest was history. The moment was caught on TV, so it has been fun to go back and watch our jubilation when I tell that story.

•What is your guiding philosophy for your law practice?

To educate and be a trusted advisor for my clients. Estate planning is an essential part of ones life that can often be ignored for various reasons. My goal is to educate clients on the process of estate planning, how I can best be of a resource to them, and give them the peace of mind that their wishes will be implemented appropriately in the various stages of life. I strive to be the trusted advisor for my clients and to be a resource for their families to carry out legacies for generations to come.

Experience

•Represents clients in the structuring and implementation of estate plans, wills, and trusts
•Counsel’s clients through probate and trust administration
•Assists clients with business succession planning
•Serving as a corporate trustee and handling fiduciary duties associated in that capacity
•Represents trustees, personal representatives, and beneficiaries in trust administration matters.
•Served as a corporate trustee and handled fiduciary duties associated in that capacity
•Assists companies in general corporate matters including formation, drafting, or revising operating agreements or bylaws, developing, and implementing liquidation or succession plans.

Library

•Gentry Locke Adds Two New Associates to the Firm
News
May 2025