My Biggest Regret: Selling My Pokémon Games for Five Dollars

To exist is to eventually grapple with the sting of “what if.” Some regrets are trivial in the grand scheme of things—perhaps a missed opportunity to invite a middle school crush to a dance. Others are monumental pivots that reshape your trajectory for years, like the weight of a career choice accepted or declined. Yet, regardless of the burdens you carry, I suspect they wither under the shadow of my own greatest oversight. I will never truly forgive my 14-year-old self for parting with my entire Pokémon collection for the insulting sum of five dollars.

Let’s retrace the timeline. As a product of the late ’90s, my formative years were saturated with the Pokémon phenomenon. I was there for the afternoon broadcasts on Cartoon Network, the weekend pilgrimages to Blockbuster to rent the latest films, and the obsessive curation of trading cards that sat pristine in binders, never once touching a playmat. But the heartbeat of it all was the games.

My odyssey began with Pokémon Crystal. I can still recall the tactile satisfaction of that translucent, glittery cartridge protruding from my Game Boy Advance. As a child, I was mesmerized by its elegant gameplay loop. I wasn’t particularly interested in completing the Pokédex—a feat I didn’t actually achieve until 2022 with Pokémon Scarlet—but I was consumed by the classic ambition to be the very best, just as the anthem promised.

That momentum surged into the third generation with the arrival of Pokémon Ruby and Sapphire, and eventually the definitive Emerald version. I have vivid memories of my father returning home with the Emerald strategy guide and a metallic, Rayquaza-branded green tin for my cartridges—likely a relic from a GameStop pre-order. This era also gifted us FireRed and LeafGreen, the GBA reimakes of the Kanto classics. Between 2003 and 2005, for an elementary schooler, it felt like we were living through a golden age of content.

Visuals provided by Game Freak/The Pokémon Company via Typhlosion4President on YouTube

Eventually, a shift occurred—a subtle drift I can’t quite rationalize. Emerald marked my departure from the franchise for a significant stretch, even after I transitioned to the Nintendo DS. Handheld gaming fell by the wayside as I became tethered to my Xbox 360, a change likely accelerated by the novelty of having a television in my own bedroom. My middle school years were defined by anime-inspired fighters like Naruto and Dragon Ball Z, while the Rayquaza tin and its contents were relegated to a shelf to gather dust.

Then came high school—that quintessential crucible of adolescence. My palate had evolved again; while I still dabbled in anime brawlers, my focus shifted toward the competitive arenas of Madden and the “Golden Era” of Call of Duty. I spent those years navigating the digital trenches of Modern Warfare 2, Black Ops, and their successors.

I was so preoccupied with online multiplayer rankings that the quest for gym badges seemed like a relic of a distant past. I had convinced myself that I was “done” with Pokémon. I ignored two entire generations on the DS, foolishly believing I had matured beyond “Pocket Monsters.” Little did that teenager know that his future self would write these words with a 3D-printed Totodile standing guard on his desk.

Visuals provided by Nintendo via Polygon

Driven by a logic I can no longer defend, I sold that Rayquaza tin and every game inside to a classmate in a 9th-grade geometry room. The price? Five dollars. It’s a sum that wouldn’t even cover a premium coffee today. The internal workings of a fourteen-year-old’s mind remain a mystery, especially one willing to commit such a tragic error in judgment.

The remorse wasn’t vocalized immediately, but it was felt. Within a few years, I found myself borrowing my girlfriend’s Nintendo DS—since mine was long gone—to experience Pokémon SoulSilver. The handheld was literally held together by duct tape, and every battle felt like a risk to its structural integrity, yet I was hooked once more. The fire was reignited. During my college years, I found myself revisiting the classics through various emulated means, desperate to recapture what I had discarded.

Today, I still possess my second, functioning Xbox 360 and a library of games for it. But everything that came before—the GBA, the SP, the original DS, the first Xbox—is lost to time. They are ghosts of a former collection.

Reflecting on it now, I think my current tendency to hoard media is a direct psychological response to that $5 sale. It is a form of lifelong restitution for an irreversible mistake. I cling to physical copies now, even those I may never play again, simply because I know the hollow feeling of looking back and seeing an empty shelf. My Switch OLED and PS4 aren’t going anywhere.

With Pokémon FireRed and LeafGreen arriving on the Switch this week to celebrate the franchise’s 30th anniversary, I’ll finally have the chance to revisit those worlds. But the experience will be a digital one on a modern console, a sharp contrast to the tactile memories of my childhood Game Boy Advance. As for where that original handheld ended up? That’s a mystery I’ll likely never solve.

Source: Polygon