Cheshire was an assassin who was greatly skilled at martial arts.
Under the League of Assassins, Jade found her training to be alongside Jason Todd and under Bronze Tiger. As Jade did not share Jason's moral ethics, she made a point of staying with the League. Jade then took up the moniker Cheshire, though she only used it during her assassin activities.
Some time later, Cheshire was sent out by Bronze Tiger to find out about the Outlaws. There Cheshire came into conflict with Koriand'r and found herself attracted to Roy Harper. Upon returning to Bronze Tiger, Cheshire explained the true threat of the Outlaws. Along with Lady Shiva and Rictus, Cheshire later once again attacked Jason, in hopes of capturing him. As her attraction to Roy Harper grew, her loyalty to Ra's al Ghul waned. Eventually, she chose to betray the League of Assassins, becoming a solo mercenary. This career did not last long as she took the protection of Commander Knyazev and joined his special strike team, attacking the Others.