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ON PHILLIPA SOO AND THE TROUBLE with GOODNESS

Three times, hollywood optioned Ron Chernow’s biography of Hamilton. Three times, it came to naught.

“I just don’t get it,” Ron would tell his agent in the years that followed the book’s publication in 2004. “This story has all the ingredients you could possibly want: sex, violence, genius.”

When Lin optioned his book, Ron was relieved that the Founding Father who had the most dramatic and least appreciated life story would finally get his due–even though a rap musical was the last way that Ron had anticipated Hamilton getting it. Still, he knew that plenty of traps awaited anybody who wanted to adapt this story. For starters: What do you do about Eliza?

Petite and vivacious, Eliza Schuyler Hamilton won the affection of everyone she met. “She was a most earnest, energetic, and intelligent woman,” recalled one of her sons. The letters that Hamilton exchanged with his “Betsey” don’t have the lightning-flash quality of his letters to and from the witty Angelica, but they glow all the same. Eliza changed his life, and might have saved it. “I was once determined to let my existence and American liberty end together,” he wrote to her during their engagement. “My Betsey has given me a motive to outlive my pride.”

Eliza’s warmth and vibrancy made her a remarkable woman, but they also make her a challenging character: “It’s difficult to make pure goodness compelling,” Ron says.

Tommy found a solution before he even realized that they had a problem. In late 2012, he saw Dave Malloy’s stage adaptation of War and Peace, an electropop musical titled Natasha, Pierre, & the Great Comet of 1812. When the lights came up at intermission, he turned to a casting agent sitting nearby and said, “What are you waiting for?” He was talking about Phillipa Soo, the recent Juilliard grad who was making her Off-Broadway debut.

“That girl who played Natasha, she’s a star,” he told Lin the next day. “There’s just something there.”

A year later, Pippa was leaving breakfast at a diner in Washington Heights when her phone rang. (The diner had a Heights poster on the wall, a tribute to Lin. “He’s basically the mayor up here,” she says.) Tommy was calling to invite her to read Eliza in a workshop of the still-unfinished Act Two. She said yes, and came to read the role in December 2013, at the first workshop that Jeffrey produced in conjunction with the Public. “Then she was it,” says Lin, “and she was it from then on.”

Lin liked Pippa for the role because audiences instantly and instinctively warmed to her, just as Eliza’s contemporaries had done. “Pippa has this sort of elegance and this lit-from-within quality,” he says. “She’s so poised, and she’s in such control of what she can do, which is kind of amazing for an actor or actress of her age. I certainly wasn’t in control of whatever the hell I had at that age.”

Though she was young–only a year out of college–she had been performing since her early childhood in Chicago. Her father, who is a doctor, and her mother, who is active in the city’s theaters, supported her desire to perform, whether it was acting, singing, or dancing. She even did some modeling: Her half-Chinese heritage gave her a distinctive beauty. Pippa’s grandparents–her father’s mother and father–had immigrated to this country before they were married. She treasures a photo of her grandfather on the boat that carried him across the Pacific in 1949.

Eliza’s devotion was constant, but in the course of her life, and therefore in a single performance of Hamilton, virtually everything else about her changes, and fast. The swoony girl who sings “Helpless” reappears a few minutes later as a pregnant young wife, describing what kind of life she wants with her husband in “That Would Be Enough.”

As Pippa began to navigate these changes, she asked to meet with Ron Chernow. Their conversation gave her a new understanding of Eliza, as she had hoped it would, but not in the way she expected. “The impression that lasted on me more than the actual facts was how wonderful he thought Eliza was, and how that matched how he felt about his own wife.”

Ron told Pippa that during the six years he had spent on the book, Valerie Chernow had developed a powerful identification with Hamilton’s wife. “She used to say, Eliza is like me: She’s good, she’s true, she’s loyal, she’s not ambitious.’ There was a purity and a goodness about the character, and that was like Valerie,” he says. In 2006, after 27 years of marriage, Valerie passed away. For her gravestone, Ron chose a line from the letter that Hamilton wrote to Eliza on the night before the duel: “Best of wives and best of women.”

For all his early worries about the role, Ron knew as soon as he saw Pippa that the show had found its Eliza. Some friends pointed out that Pippa even looks a little like Valerie. Her ballad “That Would Be Enough,” in particular, moves him deeply. “Just heartbreakingly beautiful,” he says.