That day when the Facebook genius boy eats shit and starts his very long and heavily defended legal path toward what will likely be a very short stint at Otisville, the cushy upstate Federal prison that all the gilded fraudsters choose to do their time in.

A phrase to describe someone who is cognitively degenerating. Synonym of "going off the deep end". Can have varying degrees of severity.

Reference to the song "Hey You" by Pink Floyd. The line "and the worms ate into his brain" makes no sense in an otherwise linear and literal narration throughout the lyrics.