The word "Hustle" and "Hustler" can be viewed either negatively or positively given the situation in which the terms are used, and this is related to the infinitive "to hustle". When the connotations are positive, the term means achieving things and getting tasks done quickly, and having drive and ambition. When the connotations are negative, the term could imply disreputability, dishonesty, corruption, and even criminal activities such as illegal operations, exploiting people, prostitution and human trafficking.
The infinitive "to hustle" derives from the Dutch "to shake", or "husselen", and in the first instance is related to anything that is quick and jostling about or rushing, and in the human sense often without care. For example, is one hustles somewhere it means that they are travelling quickly, though also in a rushed and jostling manner which means they are taking effort and the trip is proving difficult. Another much more benign definition is related to sports or work and achievement, where the word is to do with the release energy as a positive notion. So describing someone as a "hustler" or a situation as a "good hustle" is positively reflecting on quick, effective, and praiseworthy actions. Someone who is bent on ambition can be described as a "hustler".
The definitions that are positive, and which can be used in a positive way, are numerous, but like many other modern colloquial terms that have developed in modern times, there are plenty of negative meaning and connotations as well. The term "hustler" can describe someone who does not play by the rules when it comes to business and enterprise, and someone who is an opportunist who deceives people to have things their way or to make money. The term stays with people who rise to dominance, and also those who stay as little more than a petty con artist who fools their targets. In general, dishonest and decadent lifestyles which involve illicit activities of any kind are also implied by the term.
The 1961 film The Hustler explores the negative concept of hustling vividly, and the film stars Paul Newman whose character, "Fast" Eddie Felson is a pool player who ends up dealing with a world of criminality and ends up in a great deal of trouble. Other examples of the word are available, such as "Charlie Hustle", who was the famous baseball player Pete Rose. He coined the term for having a very fast and aggressive playing style, which helped to lead many of his teams to victory. Interestingly in his later life, which was marked with dodgy dealing, gambling, and associating himself with questionable people, his original nick-name took on a double meaning.
In business, "hustler" can have positive and negative meanings depending on the situation and the person involved, and a specific meaning implies prostitution, whereby the prostitute hustles to make money walking the streets. It also can be used as a term to denote promotion on the street, face to face with real people, though its most negative definition can be associated the pornographic magazine "Hustler". While not everyone would agree, the fact that the magazine's title is clearly deriving from the term it applies for prostitution can be seen as negative, and has helped to bring the negative connotations of the word into the public consciousness.
From what has been discussed, it is clear that the word "hustler" is full of different yet equally inherent meanings, and is very ambiguous unless given context. On its own the word remains neutral, and the use of the word will be positive or negative depending on the situation. It can be used to appraise good work and the ambitious drive of certain people in business and in general, while it can also to mean shadier things, such as dishonesty and deception within the same setting, or in another unrelated setting. The modern world understands the sexual meanings of the word, which have been the most recent connotations to surface. Due to the wide number of meanings that the word has, it is advisable to be careful in its usage, such as adhering to the context you are in, so that offense is not caused.
Anonymous. "Hustle - definition of hustle." The Free Dictionary. 2 October 2005. https://www.thefreedictionary.com/hustle.
"Definition of hustle." WordReference.com. 2 October 2005. https://www.wordreference.com/definition/hustler
"Hustle." Online Etymology Dictionary. 2 October 2005. https://www.etymonline.com/index.php?search=hustler&searchmode=none