His boss under siege as a federal investigation racked up guilty pleas, D.C. Mayor Vincent Gray’s top aide met last month with a prominent communications consultant who assisted Monica Lewinsky during the firestorm surrounding her relationship with President Clinton.

Judy Smith, a former federal prosecutor who evolved into a high-profile communications consultant, met with Christopher Murphy, Gray’s chief of staff, on July 11 after an initial introduction in mid-June. The Associated Press first reported the contacts, though the Gray administration later provided copies of emails between the two to The Washington Examiner.