Jimmy Roper was a 'free trader', who during a small gathering of like-minded folk on the West Hill was shot in the leg by a preventiveman, an act for which the official was later prosecuted. Banks in his lecture about smuggling gave this quote:-
" One of the principal free-traders at Hastings, about the same period, was a fat, good natured fellow, named Roper,* who commanded a remarkably lucky, fast-sailing lugger, called the Little Ann. So far from assailing the ' warriors' with taunts and abuse, like the rest of his comrades, Roper conducted himself with undeviating civility; so that had it been possible for fire and water to unite, he would have been esteemed even by his opponents. He usually wore a long white frock or gabardine over his flushings, and it was his custom, when not engaged in illicit adventure, to sit smoking his pipe and swinging his legs upon a crab or capstan, fixed in the beach in front of the ' Cutter ' public-house. Feeling an interest in his favour, the author once asked him why he did not quit smuggling altogether and turn fisherman ? ' What,' replied Roper, ' would you have me sit bobbing an eel all day to catch sixpenn'orth of whiting ? No; I was born a smuggler, I was bred a smuggler, and I shall die a smuggler; but I have no wish to see my children tread in the same footsteps. If either of my boys gets into a boat, I'll either break his legs or make him a linendraper sooner than he shall learn all the trouble his father has experienced.'
Roper was also known to have acted as umpire for the annual sailing regatta during 1849