If you show up at McDonalds asking for a job and the most recent experience on your resume is a 150K job with the government, the Pimply Faced Youth doing the hiring is going to gloss right over.
Let's say the Mr. Whistle does get by the the initial screening and becomes a serious candidate. As the company is doing due diligence like reference checks and background checks, it is very easy to tank someone's chances. I'm not talking about nefarious shadow men showing up making dire innuendo. The 'secret' question to ask when checking references is "Would you hire this person again?". If the answer is no, you are black flagged at the vast majority of places.
It sure as hell does not help to google a candidate's name and the top 600 hits are news stories about looming indictments and comment vitriol both for and against.
Hope this helps.