The word “hustler” carries a variety of positive and negative connotations, mostly related to how one defines its root verb, “to hustle. ” In the former sense, it means doing thing quickly and implies drive, ambition, and speed. In the latter sense, however, it implies dishonest, disreputable, or even criminal activity, such as shady business dealings, outright swindling, or prostitution. In addition, it is also the title of one of the United States’ most controversial and widely reviled magazines.
Derived from the Dutch word husselen (meaning “to shake”), “hustle” can mean moving in a quick, rushed, sometimes rough or jostling manner (The Free Dictionary). For example, one can hustle to get to a destination, meaning that they move quickly and with effort, perhaps even with some difficulty. Another definition of the word is “to gain by energetic manner,” as in sports or work, in which case it has a positive connotation; thus, a “hustler” is someone who works quickly and with verve, showing a praiseworthy, ambitious bent.
Negative meanings of “hustler” also abound. In a morally ambiguous sense, it can also mean an aggressive or unscrupulous businessperson. A “hustler” is also synonymous with being a “wheeler-dealer,” an opportunist who profits through aggression or outright deception (WordReference. com). Hustlers in this sense can be successful in business or little more than con artists, using a speedy, thrusting manner to fool and swindle their targets. It can also imply people who live “fast” lifestyles or involvement with dishonest activities like petty theft or gambling.
One example of this appears in the 1961 film The Hustler, in which Paul Newman portrayed “Fast Eddie” Felson, a professional pool player who moves in a somewhat unsavory world and is punished for his activity by gamblers, who break his hands for defeating them. / Another, more recent example of the word’s ambiguity is former baseball player Pete Rose, nicknamed “Charlie Hustle” early in his career for his fast-paced, aggressive style, which made him a key part of several winning teams.
Years later, when he was barred from baseball for gambling and consorting with a variety of unsavory characters, the name took a darker and more ambiguous meaning, putting emphasis on his character’s less admirable aspects. While a “hustler” in business can be either a positive or negative character, depending on one’s intentions and methods, it can also connote a prostitute of either sex who “hustles” (drums up business) by walking the streets. In addition to its other definitions, “hustle” is also a slang term for soliciting business by approaching potential customers on the street (Online Etymology Dictionary).
Perhaps its most negative sexual meaning appears in the title of the pornographic magazine Hustler, which is widely denounced for its graphic, often violent depictions of women and deviant sexual activity. The mere fact that it derives its name from the slang term for prostitutes gives it a negative meaning, in addition to its content. This has perhaps tainted the word “hustler” more than any other factor. In general, “hustler” is a somewhat loaded word with ambiguous meanings. In itself, the word is neutral and can be correctly used to praise one’s ambition and motivation.
It can also occupy more morally shady territory, meaning a hard-driving businessperson with questionable (if not outright dishonest) methods, as well as mere swindlers and criminals who rely on winning their targets’ trust. In the twentieth century, the word gained a strongly sexual meaning by being applied to prostitutes and, later, to the pornographic publication. Because of its widely inclusive meaning, the word lacks neutrality and requires careful usage, since it could prove offensive in certain contexts.