It took emergency crews almost an hour to free the 48-year-old man, who had his right arm caught in the machine at a tyre factory in Minto.
Paramedics and a CareFlight trauma doctor rushed to the scene after 7pm (AEDT) on Monday.
NSW Fire and Rescue (NSWFR) officers had to cut the man free and used a scissor lift to lower him to the ground.
Its understood the man was on a platform a few metres above the ground.
A NSWFR spokesman said officers assisted staff to dissemble the machine to free the man.
The man was taken to Liverpool Hospital in a serious condition, CareFlight said in a statement.
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