different meaning

“That Bob is a Real Hustler” — Compliment or Insult?

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)....
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