Charlotte Warburton first encounters Jack Finney at his Leonardo da Vinci lecture at the Art Institute of Chicago. This is where Jack makes a wild claim—that he is a time traveler and the long-time apprentice of Leonardo da Vinci, better known as Andrea Salaì.
After claims of Jack making drunken bets with da Vinci and knowing secrets about the Mona Lisa, Charlotte is intrigued. She decides that Jack will be the subject of her next podcast series. As she reveals the oddities of Jack’s lecture, she warns that this story will turn into far more than a tale of time travel.
Charlotte is granted her first of many interviews with Jack outside the lecture hall. She plays along with his charade, quizzing him on Leonardo da Vinci facts and prying for details on Renaissance life. He explains that the 15th-century renaissance has many ties to today’s digital renaissance, and shares with Charlotte the significance that today’s technology, data, and people will play in the future.
Charlotte is surprised by his interest in technology, and skeptically plays along. Toward the end of the interview, after he has explained how he hops through time, the mood gets more serious. Charlotte and Jack discuss his death, something he knows exactly when to expect.
Charlotte continues her investigation, discussing time travel theories with Robert Mercier, a professor from her alma mater. Armed with his input, she invites Jack for their second interview at her favorite Italian restaurant. There they have lighthearted discussions about pizza and cheesecake, and Charlotte begins to quiz him about how his time traveling really works.
Jack has an answer for everything, explaining his jumps through time with technology analogies like blockchain and big data. He is unrelenting, and to prove his point, makes a wildish claim about how he and Charlotte came to meet.
Charlotte recalls a storytelling competition she had entered, and won, two years earlier. This is the specific event where Jack tells her they first met, and when he first believed they had a connection.
Charlotte begins to question Jack’s motives as he continues to explain their long history that—until this time—was unbeknownst to Charlotte. Jack recites obscure facts from Charlotte’s past, dating back to a writing contest on Leonardo da Vinci that she entered in 8th grade. She pulls away, fearful of how long this man may have been stalking her, only to find that all of his claims (so far) add up. Could he be telling the truth?
Looking for answers and a levelheaded third party, Charlotte turns to her friend Devin, a famed investigative reporter. He’s willing to support, but he’s also cautious of Charlotte getting involved with someone dangerous. Charlotte heeds these warnings, but doesn’t disclose exactly how her relationship with Jack had evolved.
She brings her investigation back to the Art Institute, interviewing the museum direction Thurman Wolf and his assistant Matthew. Neither was much help as Charlotte tried to uncover details of how Jack got to where he is, and she turns to internet research for clues.
With her online lead from Grand Marais High School looking positive, Charlotte leaves town and drives 8 hours north to Grand Marais, Michigan. A phone call to the school leads her to the Grand Marais Sheriff Station where she meets Sheriff Audrey Finney, the woman who claims to be Jack’s mother.
Later that day, Charlotte gets a tour of the Sheriff’s home where she learns the truth about Jack’s seemingly dark past.
Charlotte introduces her listeners to famous Charlatan’s from history, insinuating that Jack’s lies slotted him into that category. She confronts Jack in an angry phone call disclosing what Sheriff Finney had explained. When she regains her cool and attempts to reach back out, Jack is nowhere to be found. Not even Matthew knows where or how to reach him.
Devin calls Charlotte with new information, and she realizes that Jack may not have been the person who was lying about the past after all. Devin has found adoption records from the 90’s. It seems Sheriff Finney wasn’t Jack’s biological mother.
Armed with evidence of Jack’s adoption, Charlotte drives back up to Michigan to confront Sheriff Audrey Finney. The Sheriff comes clean, and explains how she came to find Jack in the woods and the curiosities that arose as she raised him. She explains Jack’s mental instabilities that followed him from youth into adulthood, and hands Charlotte evidence in support of his time travel claims.
This conversation changes Charlotte’s perspective and she begins to worry, was she too harsh on Jack when they last spoke? Will she ever see him again?
Charlotte presents the new evidence to Devin, convinced of what it proves. Though he is not, that does not sway Charlotte’s opinions. She realizes that this story was not about time travel, it was about understanding where we are today: an intersection of data, human capabilities, and technology that has the chance to change the world.
As fate has it, Charlotte is granted one final interview with Jack. They have a chance to clear the air and discuss what comes next. Jack’s work isn’t done; he was able to leave a surprise behind for Charlotte, only to be uncovered by her own storytelling.