He joined Senator John McCain's presidential campaign in August 2008 as senior advisor and counselor to Sarah Palin.

"[10] According to ABC News, "When the media first reported push-poll phone calls from Voter/Consumer Research, a company hired by the Bush campaign, asking South Carolinians if they knew about McCain's role in the S&L crisis and his scandal as a member of the Keating Five, it was Eskew -- Bush's South Carolina spokesman – who acknowledged, and defended, the calls.

[16] In this position, Eskew directed the administration's strategy for regional American news and specialty media, including talk radio.

[7] In November 2001, Eskew was moved to 10 Downing Street and the Foreign and Commonwealth Office in London to help plan media strategy in opposition to Osama bin Laden.

[9] He later worked as Deputy Assistant to the president and Director of the White House Office of Global Communications where he managed American press internationally and oversaw US wartime messaging.

[7] Eskew continued to support President Bush as a supersurrogate, or advisor, planning media strategy during the 2004 election.

[22] In 2008, Eskew was brought on board the McCain campaign to aid vice presidential candidate Sarah Palin in the preparation of speeches and press appearance management.

[23] Eskew's work with Palin was portrayed by actor Colby French in the 2012 HBO original film Game Change.