Note that the high school dropout mentioned -- Sidney Weinberg -- dropped out of high school over a century ago, at a time when only about 6% of students finished high school. The headline "High school dropout becomes Goldman Sachs chairman" surprises us because of our current ideas of what being a high school drop-out entails; but times have changed over the past century.

Translating to a credential which is comparably scarce right now, we should read this headline as we would read "MBA dropout becomes Goldman Sachs chairman" (currently about 9% of students obtain some form of Masters degree), which might be anomalous, but is hardly a shocking notion.