Chicago has always been about hustling or selling something. Jean-Baptiste-Point Du Sable, after being arrested by the British during the American Revolution, became the first non-native person to settle in what would become the Chicago area in the late 1780s. A successful trader, he sold out in 1800, took the money, and retired to St. Charles, Missouri. Had Du Sable been around today, he might have started a freight brokerage instead, or at the least, he might have been an early employee of...
https://www.freightwaves.com/news/an-ode-to-chicago-and-its-freight-hustlers