Smith, a 53-year-old with a demeanor that’s about equal parts aggressive and affable, has long been the face of Vice. When he was pushed out of his CEO role four years ago following revelations about a culture of sexual harassment at the company, Vice announced that he would focus on making large deals. During the period in question, Smith brokered a multi-million-dollar content-distribution deal with Saudi Arabia’s largest broadcaster, MBC, according to the contract and people familiar with the deal. He was also crucial in brokering the deal with Antenna, which is also backed by Saudi money, one person familiar with that deal said. The deal explicitly allowed Smith to cash out his shares upon a “change in control” — meaning Vice being sold or going public.