After earning a law degree in 1976 Cummings began offering free tutoring to help black students meet the state exam standards. After hearing about this, former Baltimore Delegate Lena Lee pushed him to campaign for her seat. She began fundraising for him because of how impressed she was with his efforts.

November 5th, 1996 Cummings won his first general election and was appointed to the House of Representatives. Cummings won this election by a landslide, having 83.5% of the votes against republican Kenneth Kondner. From that point on Cummings has won every election easily up until his passing. In his predominantly African American district he showed through his landslide victories that he was a consistent leader among that demographic.

In office: Issa, a California businessman, cut off Cummings’ mic during a key IRS hearing. Cumminings, unlike any other person in his seat, maintained his composure. Issa later issued a public apology that gained great attention. Cummings was being stopped in airports and stores, people were telling him, even thanking him for keeping his composure and not overreacting. While most Congressmen and Congresswomen would’ve lost their cool, Cummings keeping his composure proved he was mature enough for this job, boosting his reputation and gaining many followers.