Because Craigslist is a monopolist with no real competitive pressures. Their CEO and founder are also crunchy anti-capitalists who take pride in being luddites.

Because Craigslist is a monopolist with no real competitive pressures. Their CEO and founder are also crunchy anti-capitalists who take pride in being luddites. This endears them to much of the left-wing, San Francisco tech crowd, but their shitty UI combined with monopoly power wastes dozens of human lives worth of user hours every year.