Most Spruce Prigs were former footmen who knew the ins and outs of living in the great houses, and though they operated in a risky environment the payoffs could be immense. One enterprising soul managed to lift a gold and diamond watch from a woman at a court ball, despite the fact that she was on the arm of King George I. Another infiltrated Windsor Castle and made off with a diamond buckle. Overall, these distraction, disguise and teamwork tactics were so effective that pickpockets still use them today. The only major difference is that many thieves now use a pair of tongs rather than reaching into a pocket with their bare hands.
We actually see a lot of these distraction and disguise tactics playing out in games. While it's not necessarily used to aid in pickpocketing, it's perfectly normal in the Assassin's Creed series to hire courtesans or thieves to distract guards while you loot the chest they've left unattended. Likewise, in Dishonored Corvo attends a high society party in disguise, and though his aim is to destroy Lady Boyle, he can also make a fortune filching the guests' purses as well. (Corvo is actually not a pickpocket, but a cutpurse - someone who slices off pouches or pockets, which used to be worn on the outside of clothing. Sewn-in pockets weren't a reality until the 18th century for men, and women had to wait nearly two centuries longer.)
Improving Mechanics and Context
Overall, pickpocketing mechanics work well in all the games we've discussed. Skyrim's system is the most complex and interesting, since it calculates the percentage chance of success based on the item's weight, value and whether the target is looking at the player. Assassin's Creed, Dishonored and Saints Row's mechanics get the job done without bogging down play, but aren't particularly special or memorable. One way to improve the mechanic in action games like these would be to make pickpocketing a little trickier but still keep it brief. Developers could do this by leveraging the highly-touted impulse triggers on the Xbox One, which could offer feedback as you dip your hand into an NPC's pocket. Not enough trigger rumble and you come back with nothing, too much and you alert the mark. Alternately, games on the Playstation 4 could incorporate the touch pad on the back of the controller - though hopefully better than Assassin's Creed: Liberation did in its finicky pickpocketing system.
As for how games portray the criminal culture surrounding the craft, Skyrim actually does quite a good job with its Thieves' Guild and fences. Perhaps future games could tweak the system to include bonuses if the player tricks a mark into telegraphing the location of their valuables or have the player work in teams with NPCs. Games could include more female pickpockets as well, since they've always been prominent in the trade. Or, as games seem to be experimenting with mechanics other than killing, it would be interesting to see what developers could do with a dynamic pickpocketing system in a game where stealing, rather than killing, is the primary action.
But even if that doesn't happen, even if stealing remains a third-tier mechanic not as important as fighting or magic, pickpocketing is here to stay. It's useful, it's fun to get away with, and it has an undeniable mystique. Because one thing has never changed between the London rookeries and next-generation consoles - if you want to survive on the streets, you've got to pick a pocket or two.