Gregory Craig, White House counsel
Cost (1990): $2 million.
Assessed value: $3.4 million.
President Obama is the most recent star in Craig’s long list of high-profile clients, who include Bill Clinton during his impeachment trial, Senator Ted Kennedy, would-be presidential assassin John Hinckley, and Juan Miguel González, father of shipwrecked Cuban refugee Elián González.
Jim Messina, deputy chief of staff
Cost (2003): $320,000
Assessed value: $600,000
A longtime Washington player, Messina has been chief of staff for three congressional Democrats, including Senator Max Baucus of Montana. The legendary workaholic lives in this 1,400-square-foot, red-brick house in Takoma Park, one of the area’s most liberal neighborhoods.
Costs and assessments were obtained through land and tax records, where available.