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.
For skewed distributions, it is quite common to have one tail of the distribution considerably longer or drawn out relative to the other tail. A skewed right distribution is one in which the tail is on the right side.