She takes the pilfered picture to the lab and scans it. A print on it is a match for Jack Sylvane, but when she tries to access a computer file about it, she finds it's been restricted. Luckily, we live in modern times, so she just web-searches the name, which leads her to online articles about Alcatraz, which leads her to articles about both Deputy Tiller and Jack. Most seem to be written by a Dr. Diego Soto.
She tracks him down to a comic book shop. He's arguing with a young guy about a video game and she ingratiates herself by making a Pac-Man ref. He shakes hands with her and introduces himself. "Diego Soto. Will you marry me?" We get an info dump about how he has Ph.Ds in criminal justice, Civil War History and has written four books about Alcatraz. She introduces herself and asks for his help on a case. She shows him a copy of the stolen picture. He recognizes Warden James and Deputy Tiller. She asks him about Jack Sylvane. Jack robbed a grocery store that counted as a post office simply because it sold postage stamps, which meant Jack's crime was a federal offense. First he went to Leavenworth, where he killed an inmate who tried something in the shower, then got sent to Alcatraz. Madsen tells him Tiller was killed and Jack's prints were at the scene. "I'm sorry, but that's just not possible," Soto says. "Why not?" she asks. "Because Jack Sylvane died over thirty years ago." Madsen makes a little confused face to see us into commercials.
We rejoin the show in 1960, where Jack has been in the hole for some time. Tiller opens the door to find him trembling, his plates of moldy bread uneaten. "Come on, 2024, on your feet," Tiller says. "Let's go." Jack shuffles over to the door. "What did you say to my wife?" Jack rasps out. Instead of answering, Tiller pretends like he made a mistake. "It's Red getting sprung today, not you." Back Jack goes into his dank pit of hell. Tiller reminds him of a truth about Alcatraz: "Things can always get worse."
Present day. Jack pays a clerk at some YMCA-type place eight bucks to use the locker room. It's not a hot shower he's interested in, but a locker he opens with the key he found in his jacket. Inside are new clothes and a gun, which the clerk sees when he comes to bring Jack a towel. Jack throws him against a locker.
Madsen heads over to a place unimaginatively called Ray's Bar. A seventy-something man greets her, "Hey, Becky!" She calls him "Uncle Ray" and asks him for help on her case. Ray's not surprised to learn that somebody murdered Tiller, who was the Deputy Warden when he worked there as a guard. Soto joins Madsen at the bar. He immediately recognizes Ray. "It's an honor, sir!" He says he studied Ray and even named a character in his comic after him. Yet he never interviewed him for one of his four books on Alcatraz? Info dump: Ray isn't Madsen's biological uncle, but raised her after her parents died. She says her grandfather, Tommy Madsen, was a guard at Alcatraz with Ray. "You write about him?" Madsen asks. "Sure," Soto says, making with the shifty eyes. Soto's uncovered a death certificate for Jack Sylvane from 1976. Uncle Ray tells them to stay out of it because it's a federal case, blah blah blah, but Soto quickly talks her into sticking with it. He tells her that the last time he was on the Rock, he found a room full of all kinds of files and things he wasn't supposed to see. You'd think a prison, even a decrepit old one, would be better at locking that crap away, but apparently not. They agree to meet up again.