The Treasure of Treasure Island
Reading the classics to wade into ambiguity
My son and I are reading Treasure Island. It’s every bit as good as you might imagine (or remember). There are pirates and swashbuckling, hidden maps, sea chases and plenty of 19th century swear-words (which they call oaths). Buccaneers fight with cutlasses; it’s the very essence of pirate adventure.
But what I didn’t expect, was how morally complex the story is. The characters aren’t paragons of virtue; they’re flawed, vain, proud, miserly, petty, and meek. And I’m talking about the protagonists.
That complexity has made a big impression on my nine-year-old. The characters aren’t jostling for spots along a clear good-guy/bad-guy divide. At times, he even has trouble keeping them straight. “I think the doctor is a good guy…but I don’t like him at all,” he says, nose wrinkled in uncertainty.
Of all the books we’ve read together, this is the first time he’s had that kind of reaction. Why was moral ambiguity so common in children’s literature in the 1800s, and yet so rare today?
Take a modern “classic”: Harry Potter, for example. Harry’s often troubled by his choices. But mostly in terms of whether they’ll help or hinder his goal. There’s little genuine doubt about the kind of person he is. Even when the Sorting Hat suggests he might belong in Slytherin (to the uninitiated, that’s the same boarding-school house as his nemesis), neither the reader nor Harry himself ever really believe it. His moral compass is never in question; it’s firmly planted. So much so that other characters tend to find their own bearings by it. Harry is Hogwarts’ North Star.
Jim Hawkins, the protagonist of Treasure Island, doesn’t share that privilege. He doesn’t just question his actions, he questions his very nature. He wrestles not with “did I do the right thing?” but with “am I the kind of person who does the right thing?” And refreshingly, the answer isn’t always yes. He lies. He steals. He sneaks off. He kills. He regrets. But he keeps going. And Jim isn’t alone. The same existential doubts and behavioural traps ensnare Tom Sawyer, Alice, Huckleberry Finn, Peter Pan…
Recently, the inimitable Malcolm Gladwell produced a podcast episode about the cartoon Paw Patrol. The tone of the episode is playful, bordering on satirical. He casts himself as a new dad (which he is), pulled happily into the gravitational orbit of this cultural juggernaut (which may or may not be entirely true). The episode culminates in a heartfelt, contrarian defense of the show (classic Gladwell) linking it to a utopian vision of municipal governance and other lofty Canadian ideals.
But the real meat of the episode is in the middle section. With his colleague and oft-debate partner Angus Fletcher, the two explore the show’s more troubling subtext. Paw Patrol is accused of promoting narratives of vacuous agon: problems with self-evident solutions, solved instantly and without emotional cost (Ryder always knows the answer, the pups never fail, Adventure Bay is always safe). While this type of superficial storyline may be useful for holding a toddler’s attention, it may also be doing subtle cultural and psychological harm. By turning every crisis into an easily resolved, imaginary problem without real stakes or stress, we’re depriving children of one of early childhood’s most useful lessons: stuff can be hard, and you have to try, and to wait, and maybe fail?
Fletcher suggests that the downstream effects are profound: kids who are less creative, less confident, less patient, and ultimately less prepared for the messy, uncertain nature of adult life. I’m inclined to agree. Conflict softening may lead to longer engagement times (good for content creators), but shorter struggle tolerances (bad for kids).
And if we take Gladwell and Fletcher’s framing seriously, then moral ambiguity is the scaled-up version of the same issue. As children mature, external challenges become internal ones: the dangling cartoon car over the chasm becomes a real-life choice between bravery and self-preservation, for example. If we strip away ambiguity, and with it, complexity, we may increase entertainment value and readability, but we risk reducing our children’s capacity to think, to hesitate, to wrestle with what’s right.
It’s a common misconception that children’s literature has a long history, stretching back like other cultural traditions. In truth, it’s a relatively recent development. Before the 18th century, literature “for children” was almost exclusively religious or moral in nature: catechisms, sermons, fables designed to instruct rather than delight. The very idea of entertainment written for children simply didn’t exist.
Troublingly, the belief that children even possessed a rich inner life, a vibrant imagination, distinct emotional worlds, was far from mainstream. That idea had to be invented, too. And it came not from educators, or publishers, but from philosophers.
One of the most influential voices—and a Marshmallow favourite (see Your Blue is My Green)—was John Locke. In the late 17th century, he proposed a radical idea: that childhood was not merely a miniature or incomplete version of adulthood, but a distinct and formative stage of life. His vision laid the groundwork for thinkers like Rousseau, who argued that children are born good and are shaped (often warped) by society, and Pestalozzi, who championed the idea that empathy and creativity matter as much as knowledge. Together, they began to redeem childhood from moral didacticism and reimagine it as something deeper: a phase deserving of care and curiosity.
By the mid-1800s, amongst seismic cultural change (industrialisation, urbanisation) those philosophical ideas were coalescing into a powerful literary movement. Its force and momentum even more striking when we consider the compressed timeline: Treasure Island, Alice’s Adventures in Wonderland, The Wonderful Wizard of Oz, Little Women, The Adventures of Tom Sawyer, and Peter Pan were all written between 1860 and 1910. In the span of just fifty years, an entirely new type of story genre was born (and peaked, some might argue): one that treated children as full human beings, worthy of stories rich with imagination, danger, humour, and ambiguity.
Worth noting too, is not just what these books taught, but how they taught it: slowly. Many of the classics from this era were first published serially—one chapter at a time, week by week. Though born of economic constraint, the format fit the subject matter perfectly. Treasure Island, for example, unfolded over four months in Young Folks magazine (October 1, 1881 – January 28, 1882). That rhythm imposed a kind of structural patience: a built-in delay that invited reflection, anticipation, and conversation. Children had to wait.
In many ways the former wouldn’t be possible without the latter. Moral ambiguity requires time. It’s not something kids can absorb in a flash. It needs to simmer. They had to hold contradictory feelings about characters for weeks on end. They had time to ask questions that didn’t have tidy answers, to ponder ideas that took time to synthesise.
When we race through a story night after night, book in hand, do we short-circuit a valuable piece of that experience? What is lost when narrative complexity is consumed faster than it can be felt?
Given that our world isn’t morally straightforward, why model it that way for our kids? Over-simplicity hides twin dangers: either we raise kids that are unprepared for the morally murkiness that they’ll face, or they will adopt a binary world view. I won’t wade into politics, but it bears reminding: political polarisation is made possible by—and indeed thrives on—moral rigidity. It’s what allows a group of people to believe they are right, and worse, to believe there is only one right way to believe.
Spoiler alert: at the end of Treasure Island, the treasure is found but not fully, not cleanly, and not without betrayal and considerable loss. The conclusion becomes, in essence, a fitting metaphor for the novel as a whole. The villain escapes. The hero remains uncertain of himself. Some gold is recovered, but much is left behind, lost forever. Stevenson has the restraint to withhold the ending we might want.
Ironically, for the book that popularised the image of “X marks the spot,” thematically, X doesn’t, not really. And it’s that very refusal of total triumph, of final justice, that makes Treasure Island so enduring.
Whether Harry Potter or Paw Patrol end up in the canon is for the next generation to decide. But in the meantime, here’s my summer resolution: to read at least a few classics with my son and to read them slowly (no more than a chapter or two a week). I won’t pretend we’ll forgo the comforts of easy entertainment and binge-able page-turners—I’ll look forward to devouring a few murder-mystery novels myself, from a sun lounger—but I’ll try to keep a steady current of moral ambiguity running beneath our holiday too.
My hope is that it sharpens the one skill he’ll need most: a sense of self. It’s what he’ll lean on, in the end, to find his way through murky waters.
Put another way:
“Strike me colours and splice the mainbrace, ye lily-livered landlubbers! If it’s doubloons ye seek, ye’d best be ready to dance the hempen jig, for there be no mercy on the high seas nor quarter for the faint of heart. A fair wind and a full belly o’ grog to the brave—let the cowards scuttle back to port!”