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A wheel on your wagon broke. Your wagon can't move until it's fixed.
Jason: Now, don't you worry, y'all. I'm a carpenter, I'll have this here wagon fixed in no time.
Whitney: I'm sure glad you chose a useful profession, Jason. I don't know what we would have done if you were a banker, or heaven forbid, an accountant!
Jason: All fixed up. Let's roll out!
Mallory makes a trade for some buffalo hide blankets.
Matt gets typhoid fever.
Mallory goes hunting and shoots 4 buffalo. You got 2400 pounds of food, but you can only carry back 50.
Matt contracts dysentery.
Matt: Ah, you have to be kidding me! I haven't even recovered from my third bout of typhoid!
Jason: Don't worry, son, you'll live to see the Willamette Valley yet.
Matt: But don't you see what's going on here? The Oregon Trail is out to get me. Ever since we left Missouri, I've had one misfortune after another, and I swear that is the same tree we have passed five times.
Mallory: Look on the bright side, Matt, this can't possibly be worse than that time you were crushed by that falling boulder.
Whitney: Or that time you nearly drowned in the Kansas river.
Jason: Or when that stampede got loose and trampled you for hours? And hours? And days?
Mallory: Look, here comes another one. I bet this time is good news.
Matt gets mauled by a bear. And lives. Barely.
Jason: Get on outta here, bear. Git! Now don't let that bear get you down, son. He could have chose to maul any of us. He just chose you, because you're the weakest and most vulnerable.
Whitney: Yeah, that's right.
Mallory: Quick, get him some water!
Whitney: Oh, here you go, son!
Water is poisoned, Matt's organs are liquified.
Matt: Oh, please! You will rue the day you messed with me, Oregon Trail!
Matt is shot by a passing war party. Bitten by a rattlesnake. And goes blind.
Matt gets better.
Matt trips and falls off a cliff.