One who had a brush with the law? (9)
I believe the answer is:
constable
This clue is a double definition.
'one who had a brush' is the first definition.
(painter John Constable)
'the law?' is the second definition.
(I've seen this before)
'with' is the link.
(Other definitions for constable that I've seen before include "In England, a great painter or lowly policeman" , "British painter and police officer" , "Policeman - landscape artist" , "Flatford Mill painter" , "PC" .)