Selling my Pokémon games for $5 is my biggest regret in life

If time travel existed, I know what I would go back and change!

To live is to experience regret. Some regrets are small in retrospect, like regretting not asking that cute classmate out to the middle school dance. Others huge, like regretting turning down (or even accepting) a job offer, affecting your life and career for years to come. Whatever your regrets are, I’m sorry, but they pale in comparison to mine. I’ll never forgive 14-year-old me for selling his Pokémon games for a whopping five bucks.

Let’s back up. Like any kid straight out of the ‘90s, my childhood was full of Pokémon. Catching the anime on Cartoon Network, renting the movies from Blockbuster, collecting the cards (even if they only lived in a binder, never to be played with). Playing the games, of course.

Pokémon Crystal was my first foray into the series. I can still picture its sparkly cartridge sticking out of my Game Boy Advance. As a youngin, I was transfixed by its near-perfect gameplay loop; I didn’t have the desire to catch ‘em all (I didn’t complete my first Pokédex until 2022’s Pokémon Scarlet), but you bet I was driven to be the very best, like no one ever was.

That drive carried over to the next generation and its flagship titles, Pokémon Ruby and Sapphire, and later Emerald. I still remember my dad bringing home the strategy guide for Emerald as well as a Rayquaza-brandished green tin for storing my games, likely a preorder or purchase bonus from GameStop or another retailer. Generation 3 also saw the release of FireRed and LeafGreen, the GBA remakes of the original games. From 2003 to 2005, elementary school kids were eatin’ good, y’all.

But then something changed in me, and I can’t recall what or why. Emerald was my last Pokémon game for some time, despite me eventually owning a Nintendo DS. I stopped playing on handhelds for the most part and gamed almost exclusively on my Xbox 360. (Perhaps a line can be drawn to this from me getting my own TV in my bedroom.) Middle school me had left Pokémon behind and instead was transfixed by anime fighting games based on Naruto and Dragon Ball. That Rayquaza tin, and the Pokémon games in it, only existed to gather dust at this point.

Which brings me to high school, otherwise known as Hell for Humans Age 14 to 18. My gaming tastes had shifted once again. The anime fighters were still in regular rotation, but plenty more time was spent playing Madden and Call of Duty. We’re talking the golden era of COD for nostalgic millennials here; Modern Warfare 2, Black Ops, Modern Warfare 3, and Black Ops 2 were all released during my high school years.

You see, I was too busy getting pwned in Call of Duty’s online multiplayer to worry about earning gym badges or evolving Pocket Monsters. At this time, I was likely convinced I’d never pick up those Pokémon games again. After all, a couple of generations of games had been released on the DS, and I never played them. Perhaps 14-year-old me thought he had “graduated” to more “mature” games, and didn’t envision a future that had Pokémon in it. Little did he know that the future version of himself (hi, me) would keep a tiny, 3D-printed Totodile on his desk, watching him write (about Pokémon).

And so 14-year-old me sold that Rayquaza tin and the Pokémon games it housed to some other kid in 9th-grade geometry. For five bucks. Not even the price of an iced oat latte in the present day. I can’t explain 14-year-old me’s mindset at the time, because who truly understands the inner workings of a teenager’s mind? Especially one who would make a mistake such as this.

The regret wasn’t acknowledged at the time, but it was immediately felt. In the years to come, I’d borrow my high school girlfriend’s DS (for mine was long gone at this point) to play Pokémon SoulSilver. It was literally duct taped together, and I worried I’d break the handheld with every battle, yet I persevered. The drive to be the very best was back. In my college years, I also played plenty of Pokémon on a jailbroken iPod and my laptop through certain… means.

I still have my second, working Xbox 360, thank Master Chief, and a handful of games for it. But my gaming history before that? My Game Boy Advance, SP, DS, the original Xbox? Gone, as well as their games.

Reminiscing now, I think the reason I hoard so much media in the present day is a direct fallout of willingly parting from my Pokémon games all those years ago, my attempts at making up for that irreversible mistake. I hang onto games knowing I’ll likely never play them again. My Nintendo Switch OLED and PlayStation 4 are still around.

Pokémon FireRed and LeafGreen arrive on Switch on Friday in celebration of Pokémon’s 30th birthday as digital downloads (and not the Yu-Gi-Oh! Early Days Collection-like retro package with more GBA Pokémon titles I was hoping for). I’ll be able to re-experience them, except this time, it’ll be on my Switch 2, and not on my childhood Game Boy Advance. Where is that childhood Game Boy Advance now? Your guess is as good as mine.