What Is Anne Montgomery's Deal On Netflix's What/If?

Photo: Courtesy of Netflix.
Warning: Spoilers for What/If are ahead.
Renée Zellweger is tapping into a far more sinister character for the Netflix original series, What/If. The anthology poses a near-impossible question of morality, the tension of opportunity and temptation, and how the ripple effect of a single moment can forever alter the trajectory of someone's life.
The 10-episode series from the creators of Revenge asks the existential question, "What would you risk to have it all?"
Zellweger's calm, cool, collected – and frankly, very mysterious – character, Anne Montgomery, is both an imposing force and an enigma. Is she a venture capitalist, the ultimate conductor of revenge plots, or something even more menacing? Her personal assistant, Foster, puts it best when he says, "What motivates Ms. Montgomery is far more nuanced than I could say."
Put simply, Montgomery is a gamemaster. Exuding an unshakable level of control and cunning, she believes that nothing worthwhile is achieved without sacrifice. "What if I made you an offer too extraordinary to refuse?" she entices her pawns, a San Francisco couple trying to climb the steep ladder of success in Silicon Valley.
Sean and Lisa Donovan are a young couple looking to make big changes in their lives and careers. Lisa's start up is attempting to revolutionize drug protocols for cancer patients with molecular sequencing. Something of this scale requires quite a bit of seed money. Enter Montgomery. In exchange for a night with Sean, she will invest $80 million to finance Lisa's company, but is it worth it? Thus begins the existential struggle. Oh, and one more thing. The deal will be voided should Sean and Lisa ever discuss what happened during his night with Montgomery. The plot thickens when we discover that she might have chosen the couple in a more deliberate manner than their "chance encounter" would suggest. At least countless surveillance photos, social media posts, and newspaper clippings strewn across the floor of Montgomery's study strongly implies so.
Montgomery's motivations are murky to say the least. At the beginning, it's unclear why she wants anything to do with Sean and Lisa. What we do know is that she describes her investment in Lisa's company as purely personal.
It's not until halfway through the mini series that we get a glimpse at Montgomery's past and how she got to where she is today. It seems she has her own duplicitous investor, a man known only as Liam. He exists as a dark force of influence over Montgomery. He claims that he made her what she is. He gave her money, connections, and a purpose. He seems to be the only one that can get under her skin. Montgomery was an intern at a London bank when Liam found her and made her an offer she couldn't refuse, much like she made to Sean and Lisa. He wanted to exist in the shadows, but still be able to invest in fortune. Montgomery would do that for him. Since then, she has fallen into an all-consuming obsession with how people justify gratifying their true desires.
That might be how she became the mysterious investor she is today, but what about her past?
In a series of dark, stormy rooms, Montgomery tells Lisa, and us vicariously, about her childhood. Amid flashbacks, we see that Montgomery's home life was far from stable. She never knew her father and had a strained relationship with her mother. She claims to only have loved one person, a man named Sam who was a kind handyman. Montgomery saw him as a father figure, but he betrayed her trust by manipulating her into beginning a romantic relationship while she was still a teenager. When she became pregnant, her mother kicked her out. Her trust was forever betrayed. With no other options, Montgomery gave birth to the baby and gave it to a couple looking to adopt, but she never stopped keeping tabs on her child.
In a huge plot twist, that baby was Lisa. In her own twisted way, Montgomery believes that her mind games are her way of helping her daughter become who she was meant to be.

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