Finch and Root have to deal with the next threat by Samaritan through its appointed New York Governor Nicholas Dawson. He has funneled $12 million into a fraudulent charity, OTPS, led by a man named Jared Wilkins. OTPS has no online or public electronic presence. So Finch and Root have to discover what OTPS is a front for, and what Wilkins' story is. Meanwhile, Shaw is tasked with being the lead tail on the next number, that belonging to Tomas Koroa, a Spanish-American wine dealer who travels the world for his job. He uses his good looks and suave charm to his advantage, those assets which are not lost even on Shaw. The team believes he is the target until they catch him in a high stakes smash and grab, the modus operandi which is key to the Hole in the Wall gang, who have eluded Interpol for years. In the gang's history, only one member of the gang has ever been captured, Marko Jevdice, who was eventually killed. Shaw, using her street criminal cover, infiltrates the gang for their next job, the theft of some jewels. But not is all that it seems on the surface, with the gang, Tomas' client and the true nature of the bounty being key to discovering the entire story. Shaw finds that her cover with respect to Samaritan is most at risk in protecting the target. Through both the tasks concerning OTPS and Tomas, Finch continues to question whether if what they are doing is worth it for what seems to be the increasingly negative things they are required to do in the process.