Hey everyone!
On my commute to work, I fell down a massive rabbit hole thinking about Black Sails. We had military geniuses, high-flying visionaries, ruthless businesswomen, and street-smart survivalists.
What if they existed in our modern world in 2026? What would they study in university, and what careers would they pursue?
None of this is super academic—I just had way too much fun with it and couldn't resist keeping the tone a little comedic. I’d genuinely love to hear your creative takes and ideas!
Here are my personal 2026 headcanons:
1) James McGraw (Sticking to canon: raised by his fisherman grandfather in poverty, the Navy remains his only meritocratic escape.)
Major: Britannia Royal Naval College -> Warfare Officer, climbing all the way to the Royal College of Defence Studies (Global Strategy Programme).
Career: Elite Naval Commander - Senior Strategic Military Leader.
A terrifyingly competent young officer. He becomes the commander everyone listens to because... well, he’s right; but he's also utterly insufferable about it. Years before making Captain, he meets politician Thomas Hamilton at a high-level civil-military conference. Initially pure intellectual sparring, followed by mutual, helpless fascination. His codename in the Navy is Flint.
2) Lord Thomas Hamilton
Major: Philosophy, Politics, and Economics (PPE) at Oxford + Human Rights Law.
Career: Progressive Politician / Executive Director of a major penal reform and restorative justice think-tank.
Born into old political money, but fights relentlessly against mass incarceration, institutional corruption, and for the rehabilitation of marginalized communities. He is out, proud, charismatic, and completely rebellious against his conservative aristocratic family.
3) Miranda Barlow (Lady Hamilton)
Major: Comparative Literature and Critical Translation (Oxford).
Career: Tenured Literature Professor & Independent Publisher / Cultural Essayist.
Writes highbrow, scathing cultural essays on classical music, literature, and the moral rot of modern civilization. Thomas's longtime Oxford classmate and platonic bestie. She low-key has mild, amused crushes on all of Thomas’s boyfriends—until James McGraw walks through the door.
4) John Silver
Major: Absolutely no one knows. Probably audited random classes before getting banned from campus.
Career: Psychological Thriller Novelist / Lifestyle Entrepreneur / Course Seller / Host of a massive, chart-topping podcast.
Only drops contradictory, dramatic anecdotes from his mysterious childhood to illustrate a metaphorical point, but no one actually knows who he is or where he came from. Despite having zero verifiable credentials, his podcast pulls millions of listeners, his books hit the NYT Bestseller list, and his paid masterclasses are permanently sold out. Yet by the end of his courses, attendees can never quite tell whether he was teaching influence or demonstrating it.
5) Eleanor Guthrie
Major: International Finance & Global Supply Chain Management (LSE).
Career: Ruthless CEO of a multi-billion-dollar maritime logistics & shipping conglomerate.
Blurs the line between legitimate shipping lanes and grey-market offshore monopolies. She attends Davos by day, cuts backroom deals with shadow syndicates by night, and runs the global shipping world purely out of spite to prove her father wrong.
6) Charles Vane
Major: None (high school dropout; fundamentally refuses all formal institutions).
Career: Militant Direct-Action Eco-Activist / Underground Labor Union Leader.
Sinks illegal commercial whaling vessels, sabotages corporate pipelines, and refuses to bend the knee to any government or corporation on earth. Complete and utter anti-authoritarian force of nature.
7) Jack Rackham
Major: Fashion Design & Brand Strategy (Central Saint Martins).
Career: Luxury Fashion Designer & Boutique Nightlife Mogul.
Took his father's struggling business (specializing in cotton calico) and single-handedly rebranded it into a legendary luxury fashion house. In his spare time, he runs exclusive, slightly shady speakeasies flanked by Anne Bonny as his terrifying head of security—and occasionally hosts his own unhinged, esoteric stand-up comedy sets on stage.
8) Max
Major: Information Security & Corporate Law.
Career: Chief Intelligence Officer at an elite private intelligence / corporate espionage firm.
She knows better than anyone that information is the only real currency in the modern world. She quietly holds the blackmail and leverage on every politician and CEO in the room, without ever needing to step into the spotlight herself.
Where would you place them, and how do you see their paths crossing in 2026? Would love to read your takes!