Anthony Higgs: 10 Questions About the Quartermaster of Black Flag

Anthony Higgs isn’t just Edward Kenway’s quartermaster in Assassin’s Creed IV: Black Flag—he’s a bridge between order and chaos, a former Royal Navy man turned pirate who embodies the contradictions of the Golden Age of Piracy. His journey from a rigidly disciplined sailor to a free-roaming crew member raises compelling questions about loyalty, identity, and survival. Here are 10 inquiries that cut to the heart of his character.

How did Anthony’s time in the Royal Navy shape his approach to piracy?

Anthony’s military background instilled in him a strategic mind and a sense of discipline, which he repurposed to thrive in piracy. Unlike many crewmen who sought escape from poverty, Anthony’s expertise in navigation, ship maintenance, and tactics made him indispensable to Edward’s operations. His ability to balance structure with the fluidity of pirate life highlights how survival in the Caribbean required adaptability.

What role did Anthony play in Edward’s rise as a legendary pirate?

As quartermaster, Anthony was Edward’s right-hand man, managing the Jackdaw’s crew, logistics, and resources. He mediated disputes, ensured supplies were stocked, and even led missions when Edward was absent. Without his organizational skills, Edward’s reckless ambition might have imploded. Their partnership was symbiotic: Edward brought charisma and combat prowess, while Anthony provided stability.

Why did Anthony choose the Assassins’ cause?

Though initially apolitical, Anthony grew disillusioned with the Templars’ oppression in the Caribbean. His pragmatic alignment with the Assassins wasn’t driven by ideology but by witnessing their fight for freedom. In conversations, he admits that protecting the crew’s autonomy—and his own—meant taking a side in the ancient war, even if it meant clashing with powerful forces.

How did Anthony reconcile piracy’s brutality with his personal morals?

Piracy demanded ruthless efficiency, yet Anthony maintained a code. He avoided unnecessary violence and ensured plunder was shared fairly. In private moments, he admitted guilt over collateral damage, like civilian casualties during raids. His internal conflict reflects the broader moral ambiguity of piracy—survival versus conscience.

What was Anthony’s relationship with the crew like?

He commanded respect without authoritarianism. Unlike Edward, who inspired through audacity, Anthony earned loyalty by advocating for the crew’s welfare. He mediated fights, punished insubordination fairly, and shared hardships. Many saw him as a stabilizing force, the one who’d keep the Jackdaw afloat when Edward’s gambles seemed reckless.

How did Anthony view Edward’s obsession with the Observatory?

Anthony viewed Edward’s quest for the Observatory with skepticism. While loyal, he questioned the risk of chasing a mythical tool when the Templars were closing in. His concerns foreshadowed the cost of Edward’s ambition, and his eventual death—shot protecting Edward—underscores the tragedy of misplaced faith in a singular vision.

Did Anthony ever regret leaving the Royal Navy?

In quieter moments, Anthony admitted missing the Navy’s predictability. The navy offered purpose; piracy offered freedom, but at the price of constant danger. Yet he never romanticized his past—“I’ve spilled blood for both crowns and causes,” he once said. “Regret is a luxury dead men don’t indulge.”

How did Anthony’s skills impact the Brotherhood’s operations?

Beyond piracy, Anthony contributed to the Assassins’ logistics, organizing supply chains and safe houses across the Caribbean. His knowledge of British military tactics also helped Brotherhood operatives sabotage Templar strongholds. He was a strategist who valued preparation over bravado, a trait that saved countless lives.

What legacy did Anthony leave behind?

Anthony died protecting Edward, but his impact endured. The Brotherhood integrated his strategies into their future operations, and surviving crew members remembered him as the “backbone” of the Jackdaw. His pragmatism and loyalty became a blueprint for future Assassins who balanced idealism with practicality.

How does Anthony represent the “average” pirate’s experience?

Unlike Edward’s mythic rise and fall, Anthony’s story reflects the quieter struggles of pirates—the ones who weren’t legends but survivors. He wasn’t driven by treasure or glory but by the need to carve his own path in a world that offered none. In him, we see the human cost of piracy and the fragile line between freedom and recklessness.

Anthony Higgs’ blend of pragmatism, loyalty, and quiet resilience makes him a fascinating lens through which to explore Black Flag’s world. To delve deeper into his mind—to ask him why he trusted Edward, or how he justified piracy’s moral compromises—invite him into a conversation.

On HoloDream, he’ll share stories of life aboard the Jackdaw, the weight of duty, and what it truly meant to sail between empires.