The Unluckiest Game of Oregon Trail

Sometime during my undergrad years, I discovered that you could download The Oregon Trail for PC and play it at your leisure. No more waiting excitedly for the Thursday computer lab session, where you could maybe shoot a bear and then you’d die of dysentery and then you’d have to let your classmate have a go as you looked on frustrated. This was altogether perfect and wonderful. After all, due to the nature of Thursday computer lab sessions, The Oregon Trail was both desired and unobtainable. Urban legends of people “winning The Oregon Trail” were obvious fabrications, that shit was unwinnable – a simple fact of programming.

One of the first things I discovered upon playing The Oregon Trail in college was that: kids are stupid. My friends and I easily beat the game on the hardest level (farmer), time and time again. I suppose it takes the wisdom that only comes with age to realize that you must pack enough food, ration appropriately, and stop to rest if you get dengue fever instead of pushing on at breakneck speed so you can finish the game quickly. You could make the argument that the Thursday computer lab sessions did not provide the most conducive environment for playing this game to completion. For example, lot of emphasis was placed on finishing as quickly as possible, since saving your progress was out of the question. For this reason I am willing to entertain the hypothesis that kids are not stupid, but that elementary school computer labs are stupid. But note that these hypotheses are not mutually exclusive.

However, even as a power gamer, simple dumb luck did factor into this game. On one play through, I got nothing but bought after bought of bad luck, and I only barely finished the game with only the party leader left alive (I have surmised that your party leader will not die until everybody else in your party dies first). We had 12 head of oxen, and 10 sets of clothes (two pair for each party member, for health reasons).

Somewhere near the Kansas River Crossing, we decided to ford a shallow stream. Unfortunately, a huge wave came and washed away… 10 sets of clothes. As in, all of the clothes we owned. OK, I get it, you don’t want to wear your clothes while fording a river because they’d get all gross. Everybody must have decided to get nude before crossing, but that plan ultimately backfired because now you’ve ended up with no damn clothes at all.

After begging, bartering, and stealing from any poor sap passing us on The Oregon Trail, we ended up with 5 sets of clothes – enough for 1 per person. True, we’d have to go nude on washing day, but that is better than no clothes at all.

Then, while camping out somewhere near the Green River, thieves sneaked into our camp and made off with… 5 sets of clothes. This was a crisis situation, obviously nobody was ever wearing their clothes, and that was why they kept losing them. It was time for the leader, Old Man Willaker, to call an (all nude) group meeting.

“Guys, this is an emergency. We keep losing all of our clothes. We need to start wearing our clothes at all times.”

“Even when we’re fording rivers??”

“Yes, even when we’re fording rivers!”

Increasingly loud grumbles are heard from the group.

“What about when we’re sleeping?”

“Yes, even when we’re sleeping!”

The group erupts into shouts and swears.

“Old Man Willaker, you’re killing us here!”

“Look, I like sleeping nude as much as much as any of you, but the fact remains that our high frequency of getting nude correlates with a high frequency of losing our clothes! Look at us, we can’t even go into town to trade, looking as we do!”

“The old man has lost it!”

We tried again to get at least 5 sets of clothes for the group, but since we were further along the trail, our fellow pioneers were less likely to give us a bargain. We ended up giving somebody all of our spare axles and wheels to finally get 5 sets of clothes. Off we went! Ready to face the hazards of the trail, now that we did not have to do it nude.

Thieves raided us in the night again as we made camp near Montpelier. They made off with… 12 head of oxen. As in, every single ox we owned. As in, we literally could not move. We couldn’t make it to Montpelier to find The Ox Depot. We couldn’t decide to just fuck it and press on without recouping any of our losses. Old Man Willaker demanded to know who was on watch that night, only to find out that… we didn’t have watch. Well, that explains a lot.

We were stuck at that lousy campsite forever unless we could get more oxen. And these Montpelier pioneers were ruthless! We finally ended up trading everything we owned for 1 head of oxen. Also known as, one ox.

As we crept along at the slowest pace imaginable, just trying to get to Montpelier, Jed broke a leg. We rested a bit, but had to hit the trail again soon if we were to make it past the Sierra Nevadas before winter. Then Jed broke another leg. He was usually the one to head up the hunting expeditions, but in his state the group decided that he should stay in the wagon while the rest of the group went hunting without him.

Then Jed broke an arm. Nobody knew exactly what Jed was doing every day when they left him alone, but he really had to stop. Obviously, it wasn’t a sustainable activity. Rumours circulated that Jed had taken to wrestling bears… but nobody was ever really sure of how he kept injuring himself.

We made camp and rested for as long as we could imagine Jed would need to heal up. Then Jed broke his other arm. Well, at least whatever it was Jed had been getting up to, he couldn’t do it now that all his limbs were broken. We kept resting. Then Jed died. A fighter to the end. Sure, we all knew he was batshit nuts. But there was something in his ferocity to be respected.

Then Joe-Bob drowned as we crossed a stream which was 1 foot deep. Everybody thought he was faking it as he sputtered around in 1 foot of water.

They all laughed and said, “Oh that Joe-Bob, always the joker!”

“No, wait guys, I think he might actually be drowning…”

“Are you kidding? In 1 foot of water? He could just stand up if he wanted!”

Until he went ragdoll. And then everybody realized their terrible mistake.

This sort of luck kept up until all were dead save the leader, Old Man Willaker, who crossed the Sierras in the dead of winter alone with one ox, and barely made it to Oregon as he was possibly succumbing to disease himself.

The game chalked this up as a “win,” but honestly… should this have been counted as a win? Who actually won in this scenario? And shouldn’t the game have a mechanism that prevents every single set of clothing from getting stolen??