Reginald L. Smallwood, III partners with businesses to navigate complex transactions and the evolving legal landscape of data privacy, combining sophisticated deal execution with practical, business-minded counsel that aligns legal strategy with commercial objectives.
Reggie regularly serves as lead counsel on mergers and acquisitions, guiding clients through every phase of a transaction – from due diligence and deal structuring through negotiation and closing. For cross-border transactions, he coordinates and manages local counsel in Europe and Central America, ensuring seamless execution across multiple jurisdictions. He has developed particular depth advising companies in the technology, manufacturing, sports and health care sectors, giving him keen insight into the operational and regulatory challenges that shape decision-making in these industries.
Beyond transactions, Reggie is a trusted outside advisor on day-to-day corporate and commercial matters. He drafts and negotiates a broad range of agreements – including master services agreements, SaaS and technology contracts, licensing arrangements, vendor and procurement agreements and consulting agreements – with an eye toward protecting client interests while facilitating efficient deal flow.
Reggie also maintains an active data privacy practice. As a Certified Information Privacy Professional (CIPP/US) by the International Association of Privacy Professionals (IAPP), he helps clients identify and address data-related risks within transactions and commercial relationships before they become liabilities. He advises on privacy compliance programs, data mapping, privacy policies and notices, data processing agreements, cross-border data transfer considerations and incident preparedness and breach response.
Reggie is the co-chair of the Miles Minority Network, the firm’s affinity group supporting its minority professional community.
Before joining Miles & Stockbridge, Reggie served as a law clerk to The Honorable Robert N. McDonald of the Maryland Court of Appeals (now the Supreme Court of Maryland).
He earned his J.D. magna cum laude from the University of Baltimore School of Law, where he was a Fannie Angelos Program scholar and staff editor of the University of Baltimore Law Review. During law school, Reggie was a judicial intern for The Honorable George L. Russell III of the U.S. District Court for the District of Maryland. He is a magna cum laude graduate of Morgan State University.
Reggie was a summer associate at Miles & Stockbridge in 2019.
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