As a long-only fund — one that invests in securities for their potential gains and doesn’t short stocks, or bet on potential declines — “we benefited enormously from the Trump win,” Mr. Scaramucci said. “It’s true that contrarians often get things wrong. But when they get it right, there’s a tidal wave. Trump is an example. The conventional wisdom was that he couldn’t win. Assets were priced relative to the conventional wisdom. So when he did win, there was huge upside.”

Mr. Scaramucci attributes his contrarian view of Mr. Trump in part to the fact he lives on Long Island, a stone’s throw from his working-class parents, and not among the Manhattan elite, even though he’s an alumnus of Harvard Law School and Goldman Sachs. “Everyone in the local bar, from the bluest- to the whitest-collar workers, was voting for Trump,” he said.

But Mr. Scaramucci isn’t blindly contrarian. He did initially bet wrong on Mr. Bush. “I pivoted,” he said. “Everyone makes mistakes. The question is, How do you adapt? All entrepreneurs have to do that.”

Now Mr. Scaramucci is in the Trump inner sanctum as a member of the transition team, in a position not only to predict the future, but also to help shape it.

Not surprisingly, he’s bullish on the economy and stock market for 2017. He expects the kind of high-dividend, value-oriented stocks his fund invests in (some of its biggest holdings last year were Best Buy, Caterpillar and Boeing) to do well unless “we get to hyper-growth, in which case there will be a rotation to growth stocks.”

He said fears of a Trump-induced trade war were overblown. “No one wants a trade war,” he said. “All we’re calling for are fairer free-trade arrangements around the world.”

He added: “We’re not coming at this from a position of ideological purity. There are a lot of practical business people in the room. We’re not asking if something is right or left, but whether it’s right or wrong.”