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Dicey and her siblings get some help from Tom and Jerry when they're trying to figure out a way to cross the Chesapeake Bay. As it just so happens, Jerry has his dad's boat. How convenient.
Overall, these two are a bit bratty. Jerry lies to the Tillermans about who his parents are to make himself look more important, while Tom teases his friend and gets him to take the kids across the bay even though Jerry is strictly prohibited from sailing his dad's boat. They're also pretty ungrateful for their families:
"We live over here because my mom doesn't want to get all caught up in political circles. She says it's no good for kids. She's a regular hawkeye, my mom."
"She only wants to keep her baby boy as long as she can," Tom remarked.
Jerry flushed and bit his lip. "At least she cares about her kids."
Tom laughed. "You can't get me that way, old friend. My parents care about me—but I've made my declaration of independence, and they were smart enough to accept that. I've got my freedom."
"And I don't?"
"Not yet, old buddy. When you're ready, when you want it bad enough, you'll have the nerve to fight for it." (2.2.108-113)
These guys really contrast with Dicey and her family, don't they? The Tillermans only lie to survive, not to make themselves seem like big shots, plus these poor abandoned kids would love to have parents who cared about them and looked out for them. They have their freedom, too, but they know doing things on your own isn't all it's cracked up to be.
In fairness, though, Tom and Jerry aren't all lifestyles of the posh and privileged. The next day, Dicey does have a nice time with Jerry—his personality is a bit softer when he's not around Tom, trying to keep up and look important in front of his friend. He even mentions that Dicey would make good girlfriend material. Aw.