Card fatally shoots Gray, makes it look like a struggle, and tries to convince Michael that they can do "great things" and has always been proud of him. However, Michael, unable to forgive Card for what he did and knowing what he's capable of, shoots Card through the head, killing him in cold blood. With the help of his friends, they barely escape as Olivia Riley, a ruthless agent for the CIA who "wrote the book on counterintelligence" goes after them and swears she will not stop until they are all dead. Knowing they can't stay in the country anymore, Michael and the others (including Madeline) all attempt to leave the country with the help of Calvin Schmidt, a smuggler, but Riley tracks them down. When Riley resorts to using drug cartels to take down Michael after several failed attempts, Michael asks an old friend, CSS Agent Jason Bly, to assist him in proving Riley's betrayal, only for Bly to die in the process, along with the evidence. Not wanting Bly to die for nothing, Michael plays a dangerous game of chicken with Riley and the Coast Guard, after which Riley backs down and surrenders her complicity to the CIA deputy chief. After several months, Michael's friends are released, but Michael had to make a deal to do so; going on a deep cover job to take down the leader of a terrorist organization, prompting Fi to be disgusted, stating Michael did what he wanted to and backs away, heart-broken, leaving Michael distraught. During the 100th episode of the series, it is shown how Michael and Fiona first met as spies in Ireland. Michael is struggling to ensure his friends and family remain free of the agency's grasp on what is his final mission to clear his name. Slowly but surely Michael begins to lose himself and a firm grip on his morals, succumbing to the mission. He proves this by sleeping with Sonya and killing an old friend of his. When Michael discovers that the CIA put Simon in charge of the capture team, he begins to question their beliefs. Michael kills Simon just as the capture team's backup arrives, and decides to protect James. He admits his deception to James, who is angry, but has the plan to continue his organization by putting Michael and Sonya in charge, and allowing Michael to "capture" him. Michael's friends refuse to