A 17 year old kid was given an old iPhone for free, and using the “barter” section of Craigslist made 14 trades, ending with a Porsche. Along the way he traded for newer phones, computers, motorcycles, and eventually cars.
Free services like Craigslist have decimated the classified advertising departments of newspapers, some of which depended on classifieds for 70% of their ad revenue. Research has shown that Craigslist cost the newspaper industry $5.4 billion from 2000-2007.
A bank robber hired decoys on Craigslist and escaped down a creek on a Inner tube.
There is a strange subculture of Craigslist art, which involves artists posting offbeat requests on craigslist and seeing what happens. Some examples:
Kenneth Tam offered cash to any couple who would let him observe, and film, an ordinary dinner in their home while he sat, silent, in the background.
A California teenager traded up an old phone on Craigslist for different items until he eventually acquired a Porsche.
A bank robber escaped the scene of a crime by arranging (via Craigslist) for a dozen identically dressed and unwitting civilians to be standing at the exact place and time of the arrival of the armored car he intended to hijack.