In October 1926, Ollie May Cooper became the first Black woman admitted to the D.C. Bar by examination, and later became the first Black woman to own and operate a law firm partnership in the District of Columbia. The WBA created the Ollie May Cooper Award in 1978 to recognize Cooper’s role as a legal pioneer who served the District of Columbia, Howard University School of Law and the Washington Bar Association for more than 40 years as a staunch advocate for Black lawyers. The award is presented annually to a distinguished WBA member who makes outstanding contributions to the Bar and the legal profession, and whose leadership enhances the image of the WBA and the legal community at large.

Bolden, a partner in Reed Smith’s Global Regulatory Enforcement practice, serves as managing partner of Reed Smith’s Washington, D.C. office, a role he has held since 2018, and previously from 2008 to 2014. He also served on Reed Smith's Executive Committee overseeing management of the firm's 1,800 lawyers and 30 offices worldwide. Bolden is a member of the firm’s Racial Equity Task Force, convened in the wake of the racial justice protests of 2020, which is designed to deconstruct barriers to equity in the legal industry and in our communities. The task force guides and animates the firm’s Racial Equity Action Plan, Reed Smith’s commitment to hiring, retaining and promoting Black lawyers and to advancing pro bono initiatives that benefit Black communities.

Bolden maintains a successful and robust litigation practice with clients nationwide in many major high-profile cases. Named by the Washington Business Journal as a Top Lawyer in the white-collar category, Bolden is a go-to lawyer for corporations and individuals contending before – or against – federal and local governments. Bolden’s current and former pro bono and nonprofit clients include several national African American community-based organizations, such as the NAACP, the Washington Urban League, Morehouse College and Howard University; as well as the National Bar Association, National Medical Association, National Dental Association, Joint Center for Political and Economic Studies, the National Newspapers Publishers Association and the Congressional Black Caucus Foundation. Outside of his firmwide responsibilities, Bolden regularly provides legal and political commentary to several national and local media outlets, including CNN, Fox News, CBS, WUSA9 and more.