WHHS alum Jerrold Fine was a pioneer in finance, now he is a storyteller

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Curtis Johnson

Jerrold Fine, ’60, visited WHHS on his book tour for his first novel Make Me Even and I’ll Never Gamble Again. Fine founded a hedge fund and worked on Wall Street, but retired to writing as of 2014.

Jerrold Fine’s eyes fly open in the middle of the night, his hand already reaching for the pen he keeps by his bed. Fine writes quickly, guided by a familiar voice in his head. The voice belongs to Rogers Stout, the fictional narrator of Fine’s novel.

Make Me Even and I’ll Never Gamble Again tells Rogers’ story as he comes of age and navigates Wall Street as an outsider. Fine, a first time author, is an experienced hedge fund manager and investor himself. His own life inspired him to tell a story that teaches the lessons he has learned through a different lens.

“I absolutely didn’t want it to be the Jerry Fine story.” Fine said, “If it were to be factual, autobiographical, I would just be telling my story. So what? Whereas here I can let my creativity fly.”

Rogers Stout’s story begins similarly to Fine’s. Both grew up in Cincinnati, with dreams of playing major league baseball. Both attended the University of Pennsylvania. And both, curious and brave enough to go against the grain, found themselves on Wall Street in the turbulent ‘70s.

Fine built the story around elements like baseball, poker and business. These themes represent the universal lessons that Rogers learns.

Fine admitted that the symbolism of baseball is the most difficult to pick up on. Rogers, like Fine, was the captain of his high school baseball team. Although neither knew they would end up in finance, their experiences on the pitcher’s mound prepared them to face the pressure.

“They give you the ball, you walk out, you stand on the mound.” Fine said, “Everyone is looking at you, the pressure’s on you. You have to decide what you’re going to do… You have to have confidence in yourself. You have to know what you’re doing.”

Poker teaches Rogers to adapt quickly.

“You can study poker, you can count the cards, you can know all the probabilities, but every time a card turns over, everything changes,” Fine said.

Of course, Rogers eventually begins his new life on Wall Street. Fine views succeeding there as not only a science, but also an art and way of thinking.

“You have to have the ability and discipline to listen, ask questions, and have the guts to make a decision,” Fine said.

Rogers’ story ends there, but Fine’s took yet another turn as he began to pursue writing in 2014.

“I’ve always viewed myself as a storyteller,” Fine said.

Becoming an author was a risky choice, but Fine said he never regretted it. The character Rogers Stout came to him, and Fine knew he had to tell that story.

From pitching, to investing, to scribbling down ideas in the dark, Fine had countless opportunities to doubt himself. He never did.