Tom Fitzgerald

Tom Fitzgerald advises law firm leaders on mergers and acquisitions, succession planning, compensation, market positioning, and the management decisions that shape a firm’s long-term direction. His perspective is grounded in nearly two decades leading Winston & Strawn through a period of significant growth, expansion, and organizational change.

Tom became Winston’s Managing Partner in 2006 and later served as Chair after the firm reorganized its leadership structure in 2017. During his tenure, Winston more than doubled its revenue, grew into a billion-dollar global law firm, and expanded its international and domestic footprint to 16 offices. He helped guide the firm through changing market conditions, major investments in talent and geography, and the continued expansion of core practices including litigation and private equity.

Having spent years making decisions from the top of a major law firm, Tom brings a perspective that extends well beyond outside advisory work. He understands the competing interests firm leaders must balance when evaluating growth, partner compensation, succession, lateral investment, combinations, and changes to a firm’s structure or strategy. He also understands how those decisions are received across a partnership and what it takes to move a firm from discussion to execution.

At Oxford Strategic Legal Advisors, Tom works with chairs, managing partners, and executive committees confronting many of the same questions he faced while leading Winston. His experience gives clients a practical sounding board on when to pursue growth, when to change course, how to build consensus, and how to position a firm for its next stage.

After 17 years in firm leadership, Tom stepped away from the chair having helped oversee one of the most consequential periods in Winston’s history. He now brings that experience directly to law firms navigating their own periods of growth, transition, and change.