Hard Worker . . . or Swindler?
Calling someone a “gem” or a “sweetheart” is clearly a compliment.
Meanwhile, the terms “thug” and “jerk” are clearly a dis.
But, what does the speaker mean when they call someone a “hustler?” — as in, “That Bob, he’s a real hustler!” (note: “Mary” and “she” works just as well).
It all depends on the tone (approval or disgust) and context:
Good: “That Bob, he’s a real hustler. He came up with a new product idea, and the company already promoted him.”
Bad: “That Bob, he’s a real hustler. He put his clients into a sleazy investment and lost all their money.”
The first kind of hustler is also commonly referred to as a “go-getter.”
See also, “Why is Calling Someone ‘a Piece of Work’ an Insult?”; “Interesting” vs. “I-n-t-e-r-e-s-t-i-n-g“; “Which “Done” Did They Mean?“; “The Many Guises of “Hot Dog’“; “You’re . . . You’re . . . Such an Almond! (Huh??)“; “Induct” vs. Indict”; and “Re-Duded Home.”