Prior to his current position, DeStefano worked for Ohio Republican Congressman John Boehner. From 2007 to 2011, he was Boehner's political director. From 2011 to 2013, when Boehner was Speaker of the United States House of Representatives, DeStefano served him as senior adviser. DeStefano also worked for the Republican National Committee building "a 2016 voter file and political database."
DeStefano's appointment as the Trump administration's director of presidential personnel drew strong criticism from some conservatives. "What? Trump appoints John DeStefano, a longtime aide to former House Speaker John Boehner, as Director of Presidential Personnel for the entire administration!" conservative radio host Mark Levin posted on January 4, 2017. Conservative political activist Richard Viguerie's organization ConservativeHQ said DeStefano's appointment was designed "to funnel Capitol Hill staffers loyal to the congressional Republican establishment into key jobs in the executive branch." The organization also pointed out that DeStefano has zero experience in human resource functions, which are at the core of his new role.
On the evening of January 30, 2017, John DeStefano wrote the letter to Acting Attorney General Sally Yates informing her that "the president [had] removed [her] from the office of Deputy Attorney General of the United States." Yates' dismissal was a result of her decision to inform the United States Department of Justice that she did not see defending Trump's executive order "Protecting the Nation from Foreign Terrorist Entry into the United States" as consistent with her responsibilities.
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