She joined the United States Army's Judge Advocate General Corps after law school, serving at the rank of Captain as an assistant for intelligence and special operations in the office of the Army's general counsel. That office detailed her as a Special Assistant U.S. Attorney for the Southern District of Florida to assist with the use of classified information in the prosecution of Panamanian military leader Manuel Noriega.
Justice Department
After completing her four-year obligation to the U.S. Army, Wilkinson became a full-time Assistant U.S. Attorney for the Eastern District of New York in 1991, prosecuting various kinds of cases including narcotics, white collar offenses, and violent crimes. Among her cases was the first United States prosecution of a bombing of an airliner—the 1994 case against Colombian narcoterroristDandeny Muñoz Mosquera, whom she successfully prosecuted for the bombing of an Avianca civilian airliner as well as murder of U.S. citizens and other drug-related crimes. Wilkinson won the Justice Department's highest honor, The Attorney General's Exceptional Service Award, for her work on the Mosquera case. She then became special counsel to the deputy attorney general, advising the top management of the Department on criminal policy and investigations. She was promoted to principal deputy of the Department's Terrorism and Violent Crime Section, and it was in that capacity that she participated in the trial team in U.S. vs. McVeigh and Terry Nichols. She won the Attorney General's Exceptional Service Award an unprecedented second time.
After the Justice Department
After leaving the Justice Department, Wilkinson became a co-chair with Gerald Kogan of the Constitution Project's Death Penalty Committee of the Criminal Justice Program, "a bipartisan committee of death penalty supporters and opponents who all agree that the risk of wrongful executions in this country has become too high." She also became a partner in Latham & Watkins, LLP, Washington, D.C., where she co-chaired the White Collar Practice Group and advised clients on internal investigations.
In 2006, Fannie Mae recruited Wilkinson as parts of its effort to rebuild its relationship with regulators after accounting scandals and complaints about its corporate culture. Her compensation at Fannie Mae was not disclosed when she was hired. She served as Fannie Mae's executive vice president, general counsel and corporate secretary from February 2006 until September 2008. She resigned her position at Fannie Mae along with three other senior executives on September 19, 2008, after the troubled mortgage giant was taken over by the government.
In a letter addressed to Congress on February 10, 2016, Wilkinson announced that she was representing four of Hillary Clinton’s closest aides: Cheryl Mills, Heather Samuelson, Jake Sullivan, and Philippe Reines.
In June 2020, Wilkinson represented Federal Judge Emmet G. Sullivan before the United States Court of Appeals for the District of Columbia Circuit, which was concerned with resolving Michael Flynn's petition for writ of mandamus in a criminal proceedings against Flynn. As a trial judge Sullivan didn't immediately grant the United States Department of Justice's request to drop criminal charges against Flynn, subsequent to Flynn's guilty plea, but appointed retired United States District JudgeJohn Gleeson as a "friend of the court" and scheduled an oral argument on government's motion. Before the hearing The Washington Post described Sullivan's hiring of an attorney as a "rare step that adds to this criminal case’s already unusual path".
Personal
She married David Gregory, the former moderator of NBC News' Meet the Press in June 2000. They have three children. Her husband practices Judaism while she is a Methodist. Wilkinson was previously married to Timothy Ogilvie, a Washington, DC consultant. The couple had no children and later divorced. She is a close personal friend of former Supreme Court nominee Merrick Garland.