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Jake doesn't get fired, but through a twisted turn of events Rowan eventually gets reinstated as Command and Jake flies off with Olivia to a remote island off the coast of Zanzibar for 4 months ("standing in the sun"). Jake was named the director of the National Security Agency, and then 2016 Republican vice-presidential nominee.
Olivia and the team investigate the case after figuring out that the CIA Director's suicide was actually a murder. Olivia gets to know Captain Jake Ballard (Scott Foley), who works with the leader of B613, Rowan , who orders Jake to get close to Olivia. At the end of the season, Mellie gives Fitz an ultimatum: either he becomes loyal to her, or ...
Olivia asks Fitz to free Jake so that her father’s threat will no longer be valid. Unbeknownst to her, the only way Fitz is able to grant Jake’s freedom is by confirming his affair with Jeannine. Meanwhile, Quinn, obsessed with hacking, hacks into Olivia’s email account after seeing Eli at the office.
Rowan continues to try to make everyone believe Jake is guilty, which inspires Olivia to find out the truth for herself. After forcing Tom to reveal Rowan as his operator, Fitz, Jake, and Olivia make a plan to arrest Rowan. Unfortunately, the plan fails, causing Rowan to shut down B613 and start eliminating B613 agents.
After killing Andrew, Olivia stays with Rowan and Jake. While faking her depression, Olivia discovers Rowan's plan to get Jake elected Vice President with Edison by marrying him to Vanessa. Jake and Olivia however reconcile and plan to escape together. However when Rowan threatens to kill Jake if he chooses Olivia, Olivia breaks up with him and ...
Olivia's and Jake's uncommitted relationship turns flamboyant when power rises to Olivia's head and she begins to treat him as an employee. Cyrus thinks about becoming the next president, but his ideas fade after Mellie declares how grateful she is for all he has done. Olivia is interviewed by Curtis Pryce and the two end up in an affair.
Peus visits Olivia and tries to make her force Jake to resign as vice president, otherwise he will leak photos of Jake cleaning up Elizabeth's body. Jake does step down. Huck flies a drone (potentially carrying a bomb) onto the White House in order to get the secret service to take Mellie and Fitz away from Ms. Ruland.
The mystery man tells Jake he wants to meet with Olivia. OPA and David figure out that Governor Reston is working with Billy Chambers to out Defiance. Cyrus meets the mystery man who tells him to show Fitz Olivia and Jake’s sex tape. Olivia calls Cyrus to warn him about Reston, leading to Cyrus' heart attack. David gives the Cytron card to Billy.