 Engskov started his career at the White House working for the travel office in 1993 shortly after the White House travel office controversy erupted; his work in keeping travel for White House correspondents flowing smoothly during the transition was praised by a "Washington Times" reporter, who wrote that Engskov "stood out, clearing travel plan hurdles with his dry humor and confidence," as when he stepped in to convince the Air Force not to block takeoff of a charter flight whose pilot had no money to pay for fuel at Andrews Air Force Base.He then worked as an assistant press secretary for about two years, during which Clinton once made an April Fools' Day announcement of Engskov to replace an injured Mike McCurry