Cal Sweeney heads into a bank and asks to go to his safety deposit box. A woman leads him there and once in the room, they embrace, even though security captures their move. They continue hugging and Cal slowly takes a hypodermic needle out of his pocket and injects the woman in the neck. She falls to the floor. He takes out a special tool that removes the locks from the safety boxes and is able to load his briefcase with a bunch of valuables. Another clerk finds the woman on the floor and Cal Sweeney decides to kill this man.
Back in 1960, Sweeney is part of the laundry crew and is trying to make money by selling cigarettes while in Alcatraz. He tells his fellow inmate working with him to never to show your weaknesses. Just then, Sweeney is informed that Tiller is going through his jail cell. After returning to his cell to investigate what Tiller took, Sweeney says he needs to talk to Tiller.
Madsen and Soto have breakfast. Soto explains his two Ph.D. degrees, the second the result of his status going sour after publishing a theory. Madsen gets the call about the bank robbery and the two head there. Hauser is already there and explains that the vault wasn't even targeted. Turns out the security cameras were turned off. The Asian man that tried to intervene was shot dead with the same tool that removed the locks from the safety deposit boxes. Madsen interviews the female, who is still alive. She paints a picture of Cal as a charming man. They also learn that in the past, he pawned the items, so Madsen wants to send out all information to all pawnshops. Meanwhile, Cal Sweeney heads to a safety deposit box owner's house and pretends to want a detailed list of its contents. The man lets Cal into his home.
Inside, Cal asks about the objects. As he learns that a necklace was for the man's wife, Cal asks where the man met her. The man gets up to call the bank, but Cal stabs the man's hand into the table. Back in 1960, Sweeney talks to Tiller, who wants a piece of his operation. Sweeney says until he gets his box back, Tiller won't be getting any cut of his cigarette operation. Tiller isn't happy with this and sends Sweeney back to his cell. Later at the laundry service, Sweeney relays the talk with Tiller to his fellow inmate friend. This friend may have a way to get Tiller back. Another inmate they know will fake sick and Sweeney can step in serving a dinner for Tiller.
Madsen and Soto head to the house that Sweeney was at. His wife returns home at the same time and inside they find the husband dead, the work of Sweeney. Meanwhile, Sweeney has gone to another bank. Back in 1960, Sweeney and his friend help serve a dinner for Warden James and Tiller, in celebration of Tiller's birthday. Also at the dinner are Lucy and the Alcatraz doctor (Dr. Beauregard) in their 1960 form.
Back at the Alcatraz base, Madsen, Hauser, and Soto try to figure out how they can track Sweeney. Female tellers are targeted, 45-50 years old, no wedding rings. He's courting the female tellers. They spot flowers and a business tag. They head over. The woman confirms that Sweeney was there. They find out where else Sweeney has sent flowers and start heading over to a bank. Sweeney is just in the process of hitting up another bank. The teller isn't easily injected this time and she puts up a fight. Sweeney eventually subdues her and tries to make off with more contents. However, the police, including Madsen and Soto, soon surround the bank and Sweeney decides to take the bank hostage.
Back in 1960, at the Warden's residence party, Warden James says a toast for Tiller. Sweeney's friend spills coffee on Tiller and Sweeney heads after him to the washroom. There, Sweeney tries to negotiate a deal with Tiller in return for the box. Tiller says he doesn't have the box but Sweeney doesn't believe him and forces him into the toilet. Tiller uses the sharp fountain pen he just received as a gift to stab Sweeney in the leg in order to subdue him. Tiller orders Sweeney to the "hole" for 30 days inside Alcatraz.
Hauser directs Madsen and Soto to go around back to get inside the bank. Soto figures that the vents might be connected in these old buildings. Madsen drops her gun and heads in to the adjacent building. Sweeney goes back to the female teller and asks her to get him out of the bank. Madsen, meanwhile, drops in through a vent and finds Sweeney. Madsen says she's there to break Sweeney out. Madsen gets Sweeney to follow along. Meanwhile, outside, Hauser stalls so Madsen can continue getting Sweeney out. Sweeney and Madsen pretend to be hostages and sneak into a police car. Soto picks up Hauser to follow. Eventually, Sweeney catches on to the car following him and Madsen, so he tells Madsen to lose them.
In 1960, Sweeney prepares for the "hole". He's never been in there for 30 days. The friendly inmate, his cell neighbor, slides him over his tin box that he has been looking for and thought that Tiller had stolen. Sweeney loves the tin box, it was one of his only possessions, his neighbor discusses. Sweeney exposed his weakness to him and the friend took advantage of it. Sweeney stomps on the tin box before the guards come to take him away.
Back in the present, Sweeney tells Madsen to pull over, but instead she forces a crash that knocks out Sweeney. She handcuffs him to the wheel and removes the gun. Soto later adds Sweeney's photo to the captured side of the wall. The one box that Sweeney opened contained a key, similar to one that we've seen before. They hand the key over to Hauser, but only if he will say what it's for. Hauser takes the key but decides to tell them another day what the keys are for. Hauser heads into another room and hands the key (and the one from Jack Sylvane) order to a team of researchers trying to decode the mystery of what these keys open.
Warden James brings Sweeney's friendly fellow inmate down to see Sweeney in the "hole". Warden James takes two keys and opens the vault-like door. We don't get to see inside, but James pushes the friendly inmate inside and the inmate doesn't want to go in there.