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Sex has been used for years as an espionage tool, the most famous spy that used sex was Mata Hari. Thus jimmy-jeff's 2nd carrier should have caused the WH concern, was he trying to take advantage of WH staffer's to get classified information and/or to get to a place where the "pillow talk" could be useful to enemy of the state or "terrorists"? That is one concern.
But let's assume that he was just an innocent businessman who just so happened decided to begin a second job as a journalist, he was at the right place at the right time and Eberle said "you would make a good journalist, would you like to be partisan news agency's WH press correspondent?" It could all have been quite "innocent" but, jimmy-jeff had a huge tax debt and debt makes folks vulnerable to blackmail.
Because of his sextracurricular activies, he was also vulnerable to blackmail and manipulation. He just got a "respectable" job as a WH correspondent, what if a terrorist or other enemy of the state go hold of recent compromising photos of him and blackmailed him to do their bidding, plant listening devices, deliver odd envelopes containing deadly chemicals, plant bombs. His tax debt, his prostitution, his failure to pay income tax on his "wages" earned as the escort all made him an easy target of manipulation.
Jimmy-jeff was a security threat and in this day of terror as professed and proclaimed by the administration, the enhanced security measures implemented by the admin should have prevented jimmy jeff from gaining one day pass, let alone an endless supply of them.
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