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Like a song, Simpson has a chorus: I'm getting out soon. He repeats it, again and again. Not as catchy as The Simpsons theme song, but it works for this Simpson.
Perry joins the platoon when Sergeant Simpson has 120 days left in Vietnam. "The Final Countdown" is another song he might like. After that, whenever Simpson shows up, he likes to remind everyone where he is on the countdown. It's not a bragging thing—more like he's pumping himself up. Knowing he'll be out soon is what keeps Simpson going.
So it's a little weird that when his time runs out, he decides to extend his stay in Vietnam. Say what? Thing is, Captain Stewart was pressuring him to do so, not to mention he gets a promotion to Master Sergeant out of the deal. But still—he'd been so bent on leaving. Nuts.
We never fully find out why he makes that choice. It could be that he feels a responsibility to his platoon, or fears going home. Perry speculates another reason:
"Most of the guys that extended in Nam did it for the rank, but some had other things in their heads. It was as if the idea that any moment they could be killed excited them." (15.79)
You have your kind of fun, Mr. Simpson. Pokémon Go is enough of a brush with danger for our tastes.
We don't find out whether thrill-seeking, on some level, is why Simpson stays. Perry's in the hospital when Simpson goes home, so we miss out on the departure deets.
In Simpson's defense, Perry might be a bit hard on the guy for staying. There's a strong possibility that Simpson wanted to keep protecting his platoon. He's a good soldier and he looks out for his men, even if it means getting in trouble.
For instance, when Gearhart leads his first mission, Simpson argues with his orders to take cover in a place that's not exactly a great hiding spot. When Gearhart ends up getting a man killed, Simpson gets promoted above him. Baller.
He plays a similar role on their next mission, for which they travel to a village that the Vietcong had attacked. When Walowick freaks out at the horrors they see there, Simpson holds onto him to prevent him from throwing a grenade, calming him down. Which, based on the big, murderous group of Vietcong that turns out to be nearby, also turns out to be a life-saver.
It's like Perry says: "I think, if Simpson hadn't been there, it would have been worse. Much worse. He calmed us down, brought us back to ourselves. He let us be human again; in all the inhumanity around us, he let us be human again." (14.117)
The last time Simpson tries to protect his men, he fights with Captain Stewart about volunteering them too much. He loses that fight, and leaves soon after. So much for the countdown.
And then Dongan, the racist, self-serving guy who replaces him, shows what huge shoes Simpson's were to fill. That, and he doesn't even have a good theme song.