After interviewing Jessica Hamilton at the Central Receiving Hospital you will see June Ballard exiting with her lawyer and be prompted to tail June to a cafe. Follow her to the cafe in your car, avoiding either driving too closely, falling too far back or calling attention to oneself by crashing into things. Upon reaching the cafe you will hop out of your car as she enters, hide in cover by the door. Once June gets on the phone, quickly slip in without hitting anybody and sit at the second booth with the newspaper, going incognito to unlock the achievement once the scene concludes.
- Must be done on the first attempt of a tail sequence. If you fail and choose to continue you will not receive the trophy/achievement even if you do it right on the second try
- It may take a minute or more for the trophy/achievement to unlock.(confirmed on PS3)
- It may be a reference to a fictional crime-fighting vigilante known as the Shadow.