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Connor and Risa meet Roland (no last name given) in the basement of the antiques shop that's part of the unwind Underground Railroad. Roland is set to be unwound because he beat up his stepfather for beating his mother, and then his mother ended up taking her man's side.
Being treated unfairly isn't anything new for an Unwind, though, and it earns Roland no sympathy; his obnoxious attitude makes Connor his enemy. He's manipulative, "a master of structuring life around him for his own benefit" (3.23.1), and always moving, because "big sharks don't last long in captivity" (2.19.100). What do sharks have to do with anything? Well, Roland has a big shark tattooed on his arm. And no one likes sharks, making it the perfect tattoo for the closest thing to a villain in this book.
Unwinds have terrible lives, so we're tempted to feel a smidge sorry for him—until he attempts to rape Risa in the bathroom at the Graveyard, a despicable move that he must have learned from his equally despicable stepfather. When that fails, he tries to turn everyone against the Admiral. We're not sure why. Maybe he thinks he can take over? This, too, backfires and although Roland has a moment to redeem himself by piloting a helicopter to the hospital, he turns them all in to the cops when he lands and gets them thrown in harvest camp. Smooth move, tiger shark.
Unable to let it go, Roland tries to kill Connor at the harvest camp, but can't do it: "Connor can't tell whether Roland is disappointed or relieved that he's not the killer he thought he was, but Connor suspects it's a little of both" (6.56.25). Maybe he refuses because, underneath the bully façade, Roland really is a nice guy? We'll never know. He's unwound, his body parts donated to science. We hope whoever gets his brain doesn't behave the way he did.