With the events that happened at the end of Season 3, the gang has gone on to get real jobs because Finch no longer has untold wealth and he can't get to his money without Samaritan knowing about it. Thus their reasons why to laying low and off the radar so that Samaritan can't alert those working for it to take them out. So, that brings me to what the main objective was in Wingman. Root and Finch are basically stealing and then selling a Rocket Launcher, but he along with the viewer don't have any idea why this is happening. It's not until the very end when it's revealed that The Machine has been helping Root stockpile huge amounts of weapons and cash....all in the effort of helping Finch get back on his feet. There's something oddly romantic that a Machine is doing all of this just to win back Finch's trust. It's another reason why I love this show. Also great was seeing Fusco on the prowl, learning out to pick up women, thanks to his 'Wingman', which was really an undercover job that paid off with getting a Woman's phone number.