He has on clean clothes, a nice watch and bracelet. He's wearing brand new sneakers, clean. He is not poor. He is simply tired.
Now with that said we can talk about the symbols. The sign on the back right, "cashed", "for rent", signify he is tired. The key West sign over his head is a fantasy to a better, more relaxed state. The sign with the word "money" symbolizes a deep though of financial comfort. The smoke symbolizes the control over fire. It is perceived that smokers have a connection (Three of the four elements are shared by all creatures, but fire was a gift to humans alone. Smoking cigarettes is as intimate as we can become with fire without immediate excruciation. Every smoker is an embodiment of Prometheus, stealing fire from the gods and bringing it on back home. We smoke to capture the power of the sun, to pacify Hell, to identify with the primordial spark, to feed on them arrow of the volcano. It's not the tobacco we're after but the fire. When we smoke, we are performing a version of the fire dance, a ritual as ancient as lightning.
The man covering his one eye is symbolic to Illuminati. He knows more than we perceive. :)