We often fall for the illusion that life gets easier once we “make it.”
From the outside, success looks like the antidote to doubt, grief, and insecurity. But as the saying goes, the grass is always greener on the other side—until you get there and realize that even the well-manicured lawns of success can hide weeds.
Winning Benjamin–Finding Annie compels us to look beyond the achievements of high-performing characters—Halsey Taylor, Annie Jones, and Benjamin Berman—and into the flaws that challenge them.
These aren’t just cracks in their personalities; they’re the drivers of conflict, growth, and change. And in many ways, they remind us that no amount of success exempts anyone from being painfully, beautifully human.
Let’s get to know Havas’s characters to understand why no one is born perfect.
Halsey Taylor: Grief and Reluctance
A respected lawyer and former boxer, Halsey seems to have it all — professional success, respect in his field, and a reputation as an inspiring community figure.
Isn’t that what we all believe is the ultimate life goal?
But behind his strength is a man, withdrawn and emotionally cautious, who is hesitant to accept new opportunities—even when they offer healing.
His journey teaches us that emotional pain doesn’t vanish with time or success. Growth begins with risking vulnerability.
Annie Jones: Impulsiveness and People-Pleasing
Annie is bright, ambitious, and quickly rising in the world of sports management, which many aspire to.
But her confidence sometimes tips into impulsiveness, especially in romance, and she struggles to fully assert her own goals when they conflict with her father’s expectations. Don’t we all, at times, feel defeated by the weight of others’ expectations?
But as she learns to speak up for herself, Annie shows us the value of balancing boldness with self-awareness.
Benjamin Berman: Cynicism and Control
A self-made billionaire, Benjamin is used to calling the shots. But his deep distrust of lawyers and need to control Annie’s path strain their relationship. His love is real, but often expressed through manipulation and fear.
Benjamin’s arc reminds us that real leadership, especially in family, requires trust more than control.
Winning Benjamin–Finding Annie shows that great stories never begin with successful, perfect people.
It starts with those learning that their flaws don’t disappear with achievement—they just get harder to ignore. Halsey, Annie, and Benjamin grow not by being flawless, but by confronting what holds them back.
Because in the end, the grass gets greener not on the other side—but where we do the work.
Winning Benjamin–Finding Annie by John Havas is now available on Amazon.