Goldberg introduces viewers to Benita Alexander, an award-winning documentary television producer and single mother, and Paolo Macchiarini, an internationally renowned surgeon. Alexander meets Macchiarini while producing a documentary on his groundbreaking surgical techniques using stem cells in synthetic trachea transplants. Despite crossing professional lines, Alexander finds herself wooed by Macchiarini's charm, intellect and good looks, and the pair quickly falls in love. After traveling the world together, the couple gets engaged and, according to Alexander, Macchiarini tells her he wants to take over planning the wedding. It quickly becomes a grand, fairy-tale affair with an impressive guest list, including Bill Clinton, Barack Obama and Elton John. He says they'll even be married by the pope. However, weeks before their Italian wedding, Alexander realizes things aren't as perfect as they seem and uses her investigative producer skills to uncover the truth behind Macchiarini and the planned wedding.

At around the same time, the Karolinska Institute, where Macchiarini performed some of his transplant surgeries, has been digging into allegations from Macchiarini's colleagues that he fabricated parts of his medical research.  Macchiarini eventually loses his position at the institute.  His groundbreaking surgeries have been under investigation by Swedish prosecutors, and just last week he was indicted on charges of aggravated assault relating to three of his surgeries. A court date has yet to be set and Macchiarini has not yet entered a plea. He has denied all of the allegations against him.

It was one of the biggest stories of 2019 - a large criminal conspiracy to influence college admissions at several top American universities. Rick Singer, through his elaborate and illegal methods, manipulated the admissions process for rich and famous parents whose children were applying to renowned schools, including actresses Lori Loughlin and Felicity Huffman. Whoopi Goldberg guides viewers through Singer's con, how it worked and how the FBI brought him down. Viewers will hear from those who witnessed Singer's rise, a former client who says he cut ties with Singer after allegedly being encouraged to lie in his college essay, and journalists who have broken down Singer's methods. The episode will feature, for the first time on television, an audio recreation of the fascinating FBI wiretaps that captured the deal-making and scheming of the wealthy clients working with Singer and their plans to con the system to get their kids into elite colleges.