Meaning
To be doing extremely well, excelling, or thriving — where 'bad' is an intensifier meaning impressively good, the very opposite of its literal sense. To 'gwaan bad' is to be carrying on triumphantly, dominating, or living large: an artist 'a gwaan bad' is smashing it, a hustler 'a gwaan bad' is prospering. This flip of 'bad' to mean 'to great effect' runs through Jamaican speech (compare 'pretty bad'), and the phrase is a boast or a compliment, signalling real success and command.
Examples
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Since him get di new job him a gwaan bad.
Since he got the new job he's been doing really well.
'a' marks the ongoing state; 'bad' inverts to mean excellently.
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Di team gwaan bad dis season, nuh lose one game.
The team is doing brilliantly this season, hasn't lost a single game.
Applied to collective success, not just individuals.
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Yuh see how she a gwaan bad wid di business? Big respect.
You see how well she's thriving with the business? Much respect.
Often paired with praise like 'big respect'.
Origin
From 'gwaan' (English 'go on', meaning to carry on or behave) plus 'bad' used as an amplifier — a common Caribbean and African-American reversal where 'bad' denotes something impressive.
How it’s used
Context and tone decide meaning: 'gwaan bad' can also literally mean behaving badly, so listeners rely on situation. In the boastful sense it is celebratory and complimentary.