Steve Jobs was a man of boundless curiosity. The Apple co-founder, who revolutionized personal computing, music, and smartphones, was also a deep thinker with an insatiable hunger for knowledge. But there was one question he could never ask—at least, not in his lifetime.

In a 1985 talk in Sweden, Jobs revealed an unusual source of envy: Alexander the Great. The reason? The young conqueror had Aristotle as his personal mentor for over a decade. “I read this, and I became immensely jealous,” Jobs admitted. He could read Aristotle’s works, of course, but what he truly craved was interaction—an opportunity to ask questions and get answers from the philosopher himself.

And then, he made a prediction. A bold one. A hope for the future:

“My hope is that in our lifetimes, we can make a tool of a new kind, of an interactive kind… Someday, some student will be able to not only read the words Aristotle wrote, but ask Aristotle a question and get an answer.”

Decades later, Jobs’ vision seems eerily close to reality. Today’s large language models (LLMs)—the AI-driven tools powering chatbots, virtual assistants, and even historical figure simulations—may be fulfilling the dream he voiced almost 40 years ago.

The Visionary Who Saw the Future

Steve Jobs’ life was a blend of art, technology, and philosophy. A college dropout who wandered through India in search of spiritual enlightenment, he was fascinated by Zen Buddhism and intuition as much as he was by engineering and design. Though he wasn’t a coder or an engineer, his ability to foresee technological trends was unmatched. By the time he made his Aristotle prediction in 1985, Jobs had already changed the world with the Macintosh—one of the first computers to bring a graphical user interface to the masses. But he had also just been ousted from Apple in a dramatic power struggle with then-CEO John Sculley. Perhaps it was this moment of personal upheaval that led him to think beyond hardware and software. Maybe Jobs was already searching for the next frontier—one that would blur the line between knowledge and conversation.

AI: The ‘Aristotle’ of the Digital Age?

Jobs’ 1985 remarks sound strikingly similar to what AI researchers are working on today. Language models like ChatGPT, Google’s Gemini, and Meta’s Llama can simulate conversations with historical figures, drawing from vast archives of texts to generate responses that mimic their philosophies and ideas.

Had Jobs lived to see it, would he have considered these tools the fulfillment of his vision? Or would he have pushed for something even more intuitive, more seamlessly integrated into human thought? After all, Jobs wasn’t just interested in innovation—he was obsessed with making technology feel natural.

What Would Jobs Ask Today?

If Steve Jobs could interact with an AI Aristotle today, what would he ask? Would he debate the ethics of artificial intelligence? Question whether creativity can ever be truly replicated by machines? Or perhaps he’d challenge the very nature of knowledge itself—arguing, as he once did, that intuition is just as valuable as logic.

One thing is certain: Jobs was always thinking ahead. Whether he knew it or not, his dream of an interactive mentor—of a machine that could respond with the wisdom of the past—wasn’t just a fleeting idea. It was a prophecy. And today, it’s closer than ever to coming true.