Prisoners of War: Sideswipe
Featured Cartoon Appearances: More Than Meets The Eye, Roll For It
Featured Comic Appearances: G1 #2, several G2 issues
Fanfic Appearances: "Sideswipe's Excellent Adventure" by David Willis
Unlike some other Transformers, Sideswipe is not a prisoner of the war between the Autobots and Decepticons. Rather, he is a child of it. This individual, and others like him, most likely wouldn't exist if the need for warriors was not there. He has one job and he does it well. He is a warrior. Though the cartoon and the comic show little in the way of personality for Sideswipe, they do show his relationship to two separate but intermingled things: the war and his brother.
Sideswipe and Sunstreaker are close. That's obvious to anyone who watches a cartoon episode in which both are present. You see them fighting side by side, fighting each other, cracking jokes at the others' expense. You know, typical brother kind of stuff. It's unfortunate you don't see a reaction out of one of them if someone else bad talks the other, especially from Sideswipe. I think the reaction would be what someone might expect from Sideswipe: the insulting party being shoved against a wall, Sideswipe on the verge of throwing a punch, and saying something like "No one talks about my brother like that except me."
The war brings in another aspect of Sideswipe's personality. He always has to win and he'll do just about anything to do it. He has a gung-ho attitude. He gives everything he has in battle. But war is all he has to give and he knows it. This isn't a weakness, at least while the war is still raging. If the war ever stopped, Sideswipe, more than any other Autobot, would have trouble moving on. He doesn't have any hobbies. He's always focused on fighting. He has a useful gimmick but it's mostly used to get into a better position for battle or digging out future Autobot warriors or something. He has a good mind (his tech spec lists him as an intelligence of seven) but he uses it in war and has never explored other possibilities. It's never been mentioned that Sideswipe has ever even pondered what he'd do if the war ended. He probably hasn't, but entirely on accident. Sideswipe is a warrior and he's supposed to win. He just doesn't want to think about doing anything else. It's his job and whether he likes it or not he has to do it. He likes it though. The excitement, and fighting to always come out on top no matter what.
There's more to this brash approach to war Sideswipe engages in than merely doing anything to win. When have you most often seen Sideswipe doing something he probably shouldn't in the cartoon or before #41 in the G1 comic? In "Roll For It" he's right there next to his brother all the way through, no matter where it takes him. In G1 #2, he uses his rocket pack to reach the flyers overhead when previously fighting beside Sunstreaker. Doubtless there is some sibling rivalry between the two. Their arm wrestling game in a background scene in "Roll For It" displays that, as well as the dialog between them when they're fighting the jets. But there is something more behind it. He's protecting his brother on an almost subconscience level. He knows that without Sunstreaker, it doesn't matter what he does in battle, nothing will matter anymore. With Sunstreaker making no further appearances after G1 #41, you could probably guess that he's dead. What happened to Sideswipe after this? In the G2 comic, he appears to care even less about what happens to himself. He simply fights, his cause all but forgotten.
As I said, Sideswipe and Sunstreaker are close. While battling for the Autobot cause, he must also watch out for his twin brother. Both are warriors, two of the best the Autobots have. The only way he knows to protect Sunstreaker is to sacrifice himself in the fight. To make sure that before he allows Sunstreaker to bite it, he has done all in his power, even a few dirty tricks, to protect him. Without the war, Sideswipe (or Sunstreaker) wouldn't exist. Because of the war, Sideswipe may lose his best friend.
Then again, maybe Sideswipe really is a prisoner of war.