Summary: A Kobe Bryant fan is surrounded by various tormented characters. Also, there is a red string.
Insight: To truly understand this masterpiece, each image must be considered by itself, but the entire picture must be assessed as a whole.
Beginning with the maniacally smiling fellow on the left of the picture, we see the immense joy that Kobe winning a title "by himself" brought to fans. Continuing counterclockwise we encounter a bearded, balding man. It can easily be assumed that this man is European, since he looks like a stereotypical cab driver seen in 1980s movies. This is likely an allusion to Pau Gasol, and a statement that says Kobe didn't necessarily win by himself.
The child to the right of the European is clearly pained. We must assume that this character represents the brattiness that Kobe showed as a youngster in the NBA. Since the Kobe character has his back turned to the child, we can infer that he has turned his back on these childish ways. The guy with the scarf/neck brace is the definition of Los Angeles superficiality. He is turned away from Kobe and seems nonplussed. This shows that even though Kobe is a huge sports star, not all of Los Angeles is impressed with him.
The last two notable images are the dual images which represent Phil Jackson. At the top, we see controlling hands, and in the bottom right, a man with an eyepatch. The displaced hands, clearly, are a reference to Jackson's hands-off coaching philosophy. And the way that the eyepatched man and Kobe are sharing a glance confers that they know something no one else does. It is likely the eyepatch represents Jackson's leaving the Lakers for a short period before returning.
Lastly, the red string which ties everyone together is obviously a call-out to Kobe's Michael Jordan obsession, a driving force throughout his career. I think we all know what the blonde woman represents.
Estimated price at auction: $5-10 (this looks like a high school art project)