Chapter 3: Brothers at War

2. Lonely Youth?

Old Samuel had four sons and six daughters. Three sons and five daughters were born to his wife, Margaret Duval. The son and daughter born to his mistress were left in England—provided for, but excluded from Apple Group’s inheritance.

Family photos only told half the story. The Whitaker kids were scattered between New York and London, the legitimate heirs living under Samuel and Margaret’s roof. The English branch got trust funds and boarding school, but no say in Apple’s future.

The three "legitimate sons" who could shape Apple’s future were:

- Charles Whitaker: Old Samuel’s eldest, the original heir, ultimately stripped of his crown prince status and thus nicknamed “the eldest.”

- Richard Whitaker: The second son, always the backup plan—he became a stepping stone for Charles, even going to jail for his father, earning him the nickname "cannon fodder."

- Benjamin Whitaker: The youngest, who eventually controlled Apple’s second generation. His nickname, "the loner," comes from his autobiography, "Benjamin Whitaker: From Lonely Youth to Leader of the Apple Empire."

The Whitaker boys grew up in their father’s shadow. Charles was groomed for greatness, Richard was the backup, and Benjamin—the quiet one—seemed destined to fade out. Their nicknames stuck, whispered behind closed doors and immortalized in Benjamin’s tell-all memoir.

Of course, just as Old Samuel’s autobiography blends truth and fiction, so does Benjamin’s account. In the Whitaker house, innocence was a liability, and every smile hid a calculation.

As the youngest, Benjamin had no claim to Apple Group. The Whitaker family, old money to the bone, held tight to tradition: seniority ruled, and the eldest legitimate son inherited by default.

At Sunday dinners, Margaret reminded the kids that tradition mattered. The eldest sat at the head of the table, and the future was supposed to follow a script written generations ago. Benjamin watched from the sidelines, learning that in this world, rank was everything.

Compared to Charles, meticulously educated, and Richard, at least well-trained, Benjamin was almost "written off" in his youth.

Charles got private tutors and Ivy League prep, Richard was sent to military school, but Benjamin slipped through the cracks. Teachers called him "quiet but clever," but in a family that prized achievement, he was invisible.

He was a "transparent person," nicknamed "Wooden Rooster"—a jab at his quiet, unremarkable nature.

At family reunions, Benjamin’s silence was mistaken for weakness. Cousins teased him as the "Wooden Rooster," a joke that stuck. But in the Whitaker mansion, quiet often meant watchful, and Benjamin’s eyes missed nothing.

Born during World War II’s second year, when Old Samuel was mired in bankruptcy, the family’s mood was heavy. His father traveled for business, his mother cared for seven kids. Benjamin was sent to the countryside in upstate New York after weaning because his parents were too busy, only returning home at six…

Benjamin’s earliest memories were of chilly mornings in rural New York, the smell of hay and woodsmoke, and the ache of missing home. His parents visited rarely, sending letters and gifts, but he learned to rely on himself. When he finally returned to the city at six, he found a house full of strangers—siblings with alliances he didn’t understand.

By then, Charles and Richard had already begun their open and secret struggles—mostly initiated by Richard.

The Whitaker boys were rivals before they hit puberty. Richard, always feeling second-best, started challenging Charles at every turn. Their fights were legendary—shouting matches over board games, whispered threats in the hallway, each trying to win their father’s approval by outdoing the other.

As the second son, Richard never hid his envy and jealousy of Charles, especially in adolescence when provocations were frequent.

Richard’s jealousy flared up in small ways—mocking Charles’s grades, undermining him at family events, and making sure everyone knew he was just as smart, if not smarter. Margaret tried to referee, but the boys were set on collision course.

In this atmosphere, Benjamin grew increasingly introverted and sensitive. He became silent, always alone in his room, unable to fit in.

Benjamin found refuge in books and long walks around the estate. He listened more than he spoke, picking up on every tension and secret. At night, he’d stare out the window, wondering if there was a place for him in the world beyond the Whitaker walls.

“What a headache. What will this child do in the future? Anyway, he can’t be an entrepreneur…” Old Samuel would mutter over breakfast, but beneath the concern was deep pessimism.

Samuel’s worries spilled out in half-whispered complaints to Margaret as he skimmed the business section. He saw Benjamin’s quiet as a problem, not potential. Yet, sometimes regret flickered in his eyes.

In truth, this was unfounded prejudice, rooted in Old Samuel’s favoritism for Charles. Charles was the golden boy—debate team captain, valedictorian, the kind of son who made headlines. Samuel bragged about him at country club lunches, dismissing the other children’s achievements as footnotes. It was favoritism, plain and simple, and everyone in the family felt it.

But he seemed to forget that in a large family, surrounded by money and power, silence often means forbearance, not weakness. Someone who grows up in such an environment, given space to mature, can become formidable.

Benjamin’s quiet wasn’t surrender—it was strategy. In a house full of shouting, he learned to listen, to wait, to plot his own course. The Whitaker family was a chessboard, and Benjamin was patient enough to play the long game.

In fact, this prejudice would later land Old Samuel in trouble.

Years later, Samuel would realize that overlooking Benjamin was his biggest mistake. The youngest son’s patience and subtlety would reshape the Whitaker legacy in ways no one saw coming.