My dad wasn't a gangster, and he wasn't a criminal, but he sure liked to rub padded shoulders with them.

In this quote, Jerry Heller reflects on his father’s complex relationship with the underworld and the people associated with it. While Heller makes it clear that his dad was not a gangster or a criminal, he notes that his father enjoyed associating with those who were. The phrase "rub padded shoulders with them" implies that his father was comfortable in the presence of individuals involved in illegal activities and possibly admired their lifestyle, even if he did not directly partake in their actions.

The quote reveals a certain ambivalence about his father's relationship with the criminal world. Heller suggests that while his dad may not have crossed legal lines, there was an affinity or fascination with the figures who operated in that world. This creates an image of someone who, although not directly involved in crime, was still drawn to the influence and power associated with those who were.

The origin of this quote likely comes from Heller's experiences growing up and observing his father’s interactions with various figures in the entertainment or criminal sectors. As a music manager, Heller himself had close ties with the rap community, which sometimes intersected with the more questionable aspects of the industry. His commentary on his father’s behavior may be an attempt to explain how certain individuals, while not breaking laws themselves, are nonetheless attracted to the aura of those who do.

Ultimately, Jerry Heller’s quote reflects a broader theme of association and the influence of one's social circles. It highlights the way people can be connected to worlds they don't directly participate in, yet still find themselves drawn to, shaping their experiences and identities. It also touches on the complexity of relationships, where admiration or respect can exist without direct involvement in illicit behavior.