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.

Yes, but the point is in "the old days", connections counted for more, especially in Wall Street.

To be able to rise, arguably, to the top position in Wall Street is incredible (especially for a high school dropout :)

James Cayne of Bear Stearns is a college dropout. He did okay (until recently).

Very inspiring indeed!