His celebrity was transformed into international notoriety in January 1990, when he was videotaped during a sting operation smoking crack cocaine and was arrested by Federal Bureau of Investigation (FBI) officials on drug charges.

[6] While a senior and the president of the NAACP chapter, Barry heard of Walter Chandler—the only white member on LeMoyne-Owen's board of trustees—making comments that black people should be treated as a "younger brother not as an adult".

[15] While in graduate school at Fisk, Barry was arrested several times while participating in the Nashville sit-ins to desegregate lunch counters and other Civil Rights Movement events.

In a protest of their continuing disenfranchisement, African Americans had organized this party to prove that blacks wanted to vote and conducted a trial election.

[10] In 1967, Barry and Mary Treadwell co-founded Pride, Inc., a Department of Labor-funded program to provide job training to unemployed black men.

He also became a board member of the city's Economic Development Committee, helping to route federal funds and venture capital to black-owned businesses that were struggling to recover from the riots.

In response to the 1972 blaxploitation film Super Fly, Barry quickly formed a protest group named Blacks Against Narcotics and Genocide (BANG).

[41] In 1982, Barry faced re-election against a challenge from fellow Democrat Patricia Roberts Harris, an African-American woman who had served in two cabinet positions under President Jimmy Carter, as well as from council members John L. Ray and Charlene Drew Jarvis.

Though Washington experienced a massive real estate boom that helped alleviate the city's fiscal problems for a time,[4] government spending skyrocketed; the administration posted a fifth straight budget surplus,[42] but the next year struggled with a $110 million deficit.

City councilman John A. Wilson commented that "What started out to benefit the minority community at large has meant some politically influential blacks can move out to posh suburbs.

Barry began to be plagued by rumors and press reports of womanizing and of alcohol and drug abuse; in particular, stories abounded of his cocaine use in the city's nightclubs and red-light district.

In 1983, Barry's ex-wife, Mary Treadwell, was convicted of fraudulently using federal funds given to Pride, Inc., a group that helped local youth find employment.

By this time, his dominance of city politics was so absolute that he faced only token opposition in the Democratic primary in the form of former school board member Mattie Taylor, whom Barry dispatched rather easily.

[50] By this time, Barry was openly suffering from the effects of longstanding addictions to cocaine and alcohol; he would later admit that he lost control of his drug habit soon after being sworn in for a third term.

Barry was watching Super Bowl XXI in Pasadena, California when a winter blizzard struck Washington in January 1987; city crews were accused of badly mishandling the road clearing, adversely affecting local businesses.

On January 18, 1990, Barry was arrested with a former girlfriend, Hazel Diane "Rasheeda" Moore, in a sting operation at the Vista International Hotel by the FBI and D.C. police for crack cocaine use and possession.

Against these, five black jurors were convinced that the prosecution had falsified evidence and testimony as part of a racist conspiracy against Barry, and even disputed factual findings that had not been contested in court.

[63] Barry was sentenced to six months in federal prison shortly before the November election,[64] which he lost—the first and only electoral loss of his career—receiving 20 percent of the overall vote, but doing well among the voters of Ward 8.

[76] Despite much opposition, including an abortive effort to recall his 1992 council election,[77] Barry won a three-way Democratic primary contest for mayor with 48% of the vote on September 13, pushing Kelly into last place.

[78] The victory, coming after Barry's videotaped crack use and conviction shocked the nation, carried front-page headlines in newspapers such as the Los Angeles Times and Boston Globe.

[83] Wall Street, which Barry had convinced just after his election to continue investing in municipal bonds, reduced the city's credit rating to "junk status.

[84] The next two years were dominated by budgetary and policy battles between Barry and the control board—along with Chief Financial Officer Anthony A. Williams—for power over the District of Columbia's operation.

The conflict was ultimately settled when in 1997 the Clinton Administration and Senator Lauch Faircloth agreed on legislation that rescued the city from its financial crisis but stripped Barry of all authority (including hiring and firing) over nine district agencies, making them directly answerable to the control board.

Barry was left with control of only the Department of Parks and Recreation, the public libraries, and the Board of Tourism, as well as the ceremonial trappings of his office—a condition he characterized "a rape of democracy".

[93] Barry ran for re-election in 2008 and easily held off all five challengers in the Democratic primary: Ahmad Braxton-Jones, Howard Brown, Chanda McMahan, Sandra Seegars and Charles Wilson.

During his 2008 reelection campaign, Barry had told members of the Gertrude Stein Democratic Club, the city's largest LGBT political group, "I don't think you should make [supporting the bill] a litmus test.

On March 9, 2006, he was sentenced to three years' probation for misdemeanor charges of failing to pay federal and local taxes, and underwent drug counseling.

[100] According to Judge Robinson, sentencing Barry to jail without proving that he willfully failed to file his taxes would contradict precedent set by the United States Supreme Court.

"[136] Several weeks later, Barry sparked a diplomatic incident with the diplomatic mission from the Philippines, after he said at a meeting with UDC personnel that "it's so bad, that if you go to the hospital now, you'll find a number of immigrants who are nurses, particularly from the Philippines ... And, no offense, but let's grow our own teachers, let's grow our own nurses, so that we don't have to be scrounging around in our community clinics and other kinds of places, having to hire people from somewhere else.

A 1993 survey of historians, political scientists and urban experts conducted by Melvin G. Holli of the University of Illinois at Chicago ranked Barry as the eleventh-worst American big-city mayor to have served between the years 1820 and 1993.