Since he collected the keys to the mayor's office in January 2011, Vincent Gray has repeatedly struggled to hit his stride and avoid controversy.

February 2011: Gray draws attention for paying senior staff members far more than their predecessors earned as the city confronts a budget shortfall and furloughs employees. Gray also finds himself on the defensive for hiring the children of campaign aides.

March 2011: Sulaimon Brown, a minor mayoral candidate, goes public with allegations that the Gray campaign paid him to remain in the 2010 race to criticize incumbent Adrian Fenty, Gray's archrival. Gray denies any wrongdoing, but the allegations prompt a federal investigation.

October 2011: Prosecutors strike a plea deal with Howard Brooks, a Gray campaign consultant, but the agreement isn't publicly announced.

February 2012: In his State of the District remarks, Gray acknowledges "a series of missteps early in my administration."

March 2012: The FBI raids the home and offices of Jeffrey Thompson, a major contributor to Gray and other District politicians. Gray also misses a legal deadline to appoint members to the District's new ethics board, and media outlets report that Gray's campaign included an off-the-books component to help shore up voter turnout.

May 2012: Gray misses his self-imposed deadline to propose campaign finance reforms. Later, two senior aides to Gray's campaign, including Brooks, plead guilty to federal charges related to Brown's allegations. Gray, who had occasionally spoken about the investigation in the past, refuses to comment, on the advice of his criminal defense lawyer.

June 2012: Gray appoints Michael Kelly as the city's housing chief, but soon acknowledges that Kelly left his previous post after admitting to an affair with a subordinate. The same week, the Gray administration defends a plan to overhaul the city's open records laws and the mayor departs for a long-planned trip to China.