| Quote #1
Aunt Polly asked him questions that were full of guile, and very deep -- for she wanted to trap him into damaging revealments. Like many other simple-hearted souls, it was her pet vanity to believe she was endowed with a talent for dark and mysterious diplomacy, and she loved to contemplate her most transparent devices as marvels of low cunning. (1.25)
Aunt Polly's faith in her own ingenuity, the very thing that keeps Tom going, is her undoing.
| Quote #2
""Ben, I'd like to, honest injun; but Aunt Polly -- well, Jim wanted to do it, but she wouldn't let him; Sid wanted to do it, and she wouldn't let Sid. Now don't you see how I'm fixed? If you was to tackle this fence and anything was to happen to it --"
Tom's trick, however clever or charming it may be, is still a form of manipulation.
| Quote #3
The boys were all eaten up with envy -- but those that suffered the bitterest pangs were those who perceived too late that they themselves had contributed to this hated splendor by trading tickets to Tom for the wealth he had amassed in selling whitewashing privileges. (4.43)
Though Tom's whitewashing scheme is ingenious, his ability to quickly "flip" his loot and turn it into an entirely different kind of prize – both a Bible and the recognition of adults – represents a unique kind of cunning.