A Washington, D.C. native, Fenty graduated from Oberlin College and Howard University Law School, then served for six years on the D.C. Council.

He served one term as D.C. mayor and lost his bid for reelection at the primary level to his eventual successor, Democrat Vincent C. Gray.

[7] He has served as a paid speaker, part-time college professor, and adviser for state and local governments with an information technology consulting firm.

In 2000, Fenty won a seat on the Council of the District of Columbia, defeating longtime Ward 4 Councilmember Charlene Drew Jarvis by a margin of 57 to 43 percent after engaging in an aggressive door-to-door strategy.

Then-Council Chair Linda Cropp, businesswoman Marie Johns, then-Councilmember Vincent Orange, and lobbyist Michael A.

Fenty ran on a platform of bringing a more energetic and hands-on approach to district government,[citation needed], advancing bold ideas for change, and sticking to them.

[23] Fenty said he would take his uncompromising style to the mayor's office, and cited with approval, Margaret Thatcher's saying that, "Consensus is the absence of leadership".

[23] Cropp stressed her 25 years of experience in district government and her desire to continue the progress made by Anthony Williams, who endorsed her candidacy.

Cropp's campaign began running negative attack ads during the month before the primary, painting Fenty as unfit for the job and as a careless lawyer who had been admonished by the D.C.

The attacks backfired and Fenty won all 142 district precincts in the Democratic Primary—a feat unparalleled in earlier mayoral elections[27]—defeating Cropp by a 57 to 31 percent margin.

[31] At the beginning of Fenty's term, student test performance scores and graduation rates were among the lowest in the nation and District residents had been demanding that the schools be "fixed".

[35] The power shift also allowed Fenty to make swift changes in the system's central office, alter teacher qualification requirements, and implement a school consolidation process.

In choosing Rhee, Fenty consulted with national education figures including New York City School Chancellor, Joel Klein.

Additionally, the Fenty administration improved the delivery of emergency medical services and expanded health care coverage for the uninsured.

It also finalized the sale of Greater Southeast Community Hospital (now United Medical Center) in a public-private partnership that kept the facility open.

Fenty was known to carry three BlackBerry devices: one directly connected him to the police chief, the second was for other district business, and the third was for personal matters.

[48] Fenty officially launched his reelection bid in April 2010, defending his management style and pledging to remind voters that had made the types of tough decisions that are necessary for real change.

[49] On August 1, 2010, the editorial board of The Washington Post officially endorsed Fenty, citing his attempts to fix the District's struggling public school system.

[63] Since then, District law was changed to prohibit an elected official from incorporating a nonprofit organization at the end of his or her term in office and transferring constituent services fund money into it.

[64] The same month, Fenty became an outside adviser and counsel to Heffler, Radetich & Saitta, an accounting and consulting firm based in Philadelphia.

[65] Also in January 2011, it was announced that Fenty would become a distinguished visiting professor of politics, a featured lecturer and a career adviser in the Department of African American Studies at Oberlin College in Ohio.

[69] In July 2011, Fenty joined the plaintiff and litigation oriented law firm of Klores Perry Mitchell as special counsel.

[70] On Morning Joe on March 8, 2011, Fenty backed Wisconsin Republican Governor Scott Walker's anti-union efforts and broadly condemned the concept of public employee collective bargaining.