Wilder then served in the Korean War, earning a Bronze Star. After his service, he attended Howard University School of Law under the G.I. Bill, graduating in 1959 and co-founding the law firm Wilder, Gregory, and Associates.
Wilder began his career in public office after winning a 1969 special election to the Senate of Virginia from a Richmond-area district, becoming the first African American state Senator from Virginia since Reconstruction. In 1985, still holding office in the state Senate, he was narrowly elected Lieutenant Governor of Virginia on a Democratic ticket under then-Attorney General and fellow Richmonder Gerald Baliles. Upon his election, Wilder became the first African American elected to statewide executive office in the South in the twentieth century.1.
Wilder had a comfortable lead in the last polls before election. The unexpected closeness of the election, while likely due in part to the traditionally strong get out the vote efforts of Republicans, has also been observed in selected elections involving African Americans and other minority candidates. Called the "Bradley effect", it alleges that white voters being more likely to tell pollsters that they will support a candidate than to actually vote for them.
During his tenure as governor, Wilder granted a controversial pardon to basketball star Allen Iverson. Iverson, then a popular high school sports figure, was convicted after being accused of assaulting a woman in a bowling alley and sentenced to 5 years in prison. However, due to Wilder's own judgment, after Iverson had served just five months, Governor Wilder granted Iverson clemency and released Iverson from his prison sentence.
Since the 1970s Wilder has supported the death penalty and has generally run on an "anti-crime" platform. In response to a waning budget balance during his period as governor, Wilder supported some of the most dramatic cuts in allocations for higher education in the United States. He came under scrutiny in the mid-1990s for his attacks on fellow Democrat Chuck Robb and his support of Republican Mark Earley. Wilder declared himself a candidate for President in 1992 and briefly considered running for the U.S. Senate in 1994.
On November 2, 2004, Wilder received 79% of the vote (55,319 votes); R.C. "Rudy" McCollum Jr. received 11% (8,079 votes), Charles H. Nance received 8% (5,912), and Lawrence E. Williams Sr. received 2% (1,138). Free Socialist candidate, Silver Persinger ran as a write-in candidate in this election. Wilder is the first directly elected Mayor of Richmond in sixty years. Upon winning the election in November, Wilder communicated his intentions of aggressively taking on corruption in the city government by issuing several ultimatums to the sitting City Council even before he took office. He was sworn in on January 2, 2005.
He is a member of the Mayors Against Illegal Guns Coalition, a bi-partisan group with a stated goal of "making the public safer by getting illegal guns off the streets." The Coalition is co-chaired by Boston Mayor Thomas Menino and New York City Mayor Michael Bloomberg.
On 16 May 2008 Wilder announced that he would not seek reelection to another four-year term as mayor.