While he understands why some may have trouble sympathizing with a three-time drug offender, Tyler offers perspective. A life sentence, people don't really understand it. A man raped his daughter, got probation. A man killed people with his car, got probation.
A skewed left distribution is one in which the tail is on the left side. The above histogram is for a distribution that is skewed right. Skewed distributions bring a certain philosophical complexity to the very process of estimating a typical value for the distribution.
Now the picture is not symmetric around the mean anymore. For a right skewed distribution, the mean is typically greater than the median. Also notice that the tail of the distribution on the right hand (positive) side is longer than on the left hand side.