5 – Keith Schiller
Keith Schiller has been Donald Trump’s trusted security chief for the past 16 years. He started as Trump’s bodyguard in 1999, following a decade with the NYPD. Trump later promoted him to director of Oval Office operations.
Schiller is with Trump around the clock, often stepping in to manage reporters and protesters. Despite his close relationship with Trump, he is not a billionaire. Ivanka Trump also relied on him to ensure Jared’s safe return from a risky trip to Iraq.