Sidney follows what's trending and outstanding from Machiavellian type (9)
I believe the answer is:
insidious
'sidney follows what's trending and outstanding' is the definition.
I can't tell whether this defines the answer.
'from machiavellian type' is the wordplay.
I cannot really understand how this works, but
'from' could be 'in' (I've seen this in other clues) and 'in' is located in the answer.
This may be the basis of clue (or it may be nonsense).
Can you help me to learn more?
(Other definitions for insidious that I've seen before include "crafty" , "Treacherous; subtle" , "Gradually harmful" , "deceptively attractive" , "Proceeding subtly but harmfully" .)