For players who explore extensively, this achievement will be earned in the course of play. However, for people who play in a streamlined fashion, the game can be finished well short of the 100 picked pockets for this achievement. The achievement can be earned fairly early by employing the Pickpocket Loop shown in the above video. It is done in the vicinity of Garret's home, the Clock Tower. The video shows game play using the highest difficulty level--a Master custom difficulty greater than 700 points--to demonstrate that the pickpocket loop will work on any difficulty setting.
Note: I made the video playing the PS4 version. However, it is exactly the same on the XBox One. Pickpocketing is performed by holding down the
interact button until the purse is collected. A prompt, "Hold
" will appear when Garrett is close enough to a purse carrying target.
The following map depicts the path taken by Garrett in the above video.
The pickpocket loop starts from the hideout in the Clock Tower and runs a clockwise loop back to the Clock Tower. Along the way, Garrett can pickpocket four guards and one civilian. Each pocket picked will net him 12G. The loop takes a little over three minutes.
Referring to the map above, the section on the left depicts the beginning of the loop when Garrett is above street level. The section on the right depicts the second part of the loop after Garrett descends to street level. As is to be expected, all five picked pockets occur at street level.
As shown on the left hand side of the map, Garret leaves the Clock Tower and heads South. He takes the first left to head East. Right after this left turn, he has to make an adjustment to his left front to stay on the walkway. At the end of the walkway, he has to crouch down in order to make a right hand turn on another walkway running South. At the very end of this walkway, Garrett vaults the railing landing on a sloping roof and slides to street level as indicated by the red dot.
Referring to the right hand side of the map, Garrett is now at street level as indicated by the red dot. He crosses the street moving West into an enclave. At the West side of the enclave, he climbs on a crate and then over the railing. He makes a turn moving left, crouches near a crate, and sees two guards moving East to West on the street just to his South. The guards will not see him from that distance. He crouched, not for stealth, but to prepare himself for the first pickpocket. (If you do not see the guards, you’re slightly behind schedule but you have quite a few seconds of slack here so, unless you were very slow, there should be nothing of concern.)
There will be a civilian standing against the wall Northwest of the crate Garrett is crouching behind. He will stand straight and start to walk. He will look straight at Garrett. Like most civilian activity, this is of no concern. The civilian is not even curious much less suspicious. Move behind him and pickpocket him. He is much more insensitive than the guards. Unless Garrett really disturbs him, he will remain oblivious of what is going on. Garrett must, however, pickpocket him before he moves more than a few steps away from his crouched position. There is another civilian (with no purse) further North. He will become suspicious if he sees what Garrett is doing.
Reminder: Crouch while pickpocketing. You are very susceptible to detection when not crouching.
After you pickpocket the civilian, Garrett goes to the South end of the alley and crouches against the West wall. (Note: In the beginning, you may want to make a manual save you can revert to here in case of error). Peeking, Garrett sees the two guards standing West of him. After a while, they begin to move towards him. He moves back in his crouching position and waits concealed by the West wall.
Don’t be too hasty. If you are playing on Master custom difficulty, the guards are quite alert. If you approach too diagonally, the guards will sense this and detect you. You will want them to be a couple of steps East of you and try to approach them straight from behind. You can pickpocket them in any sequence. I usually find it easier to pickpocket the one on the left first.
The goal is to pickpocket them quickly and then go to the North end of the street Garrett just came from. He will then be just in time to see two guards just below. Garrett drops down behind the two guards. Make sure you are crouched because they will detect you if you are not. You have a lot of time to pickpocket them. You can do one or both quickly while they’re both still climbing the stairs or you can do the second guard or both while they are walking their long route North towards the Clock Tower.
Before the two guards stop, duck into the enclave to your left. It is on the West end of a street going East into the plaza. Wait for them to stop, turn around, and pass you going South. Then, go to the point where they stopped. There’s a climbing place against the wall. Climb up, scoot to your right, climb over the railing, and turn left to go back into the Clock Tower hideout.
Going into the hideout creates a checkpoint save. So does coming out of it. Whenever Garrett comes out of the hideout, everything is reset--purses are full and people's locations and movements start from scratch. So you are in perfect position to keep repeating the loop until you meet your pickpocket goal.