Albert Anker, Portrait of a Boy, nineteenth century.

Like many small children, my brother was an accomplished con artist. And as is often the case with little boys, his manipulations were most effective when applied to his mother. I can particularly recall one bit of business he’d pull between the ages of about three and five, when we were at the market and he didn’t feel like walking. He’d gaze up at her beseechingly, bat his eyelashes, and simper, “I’ll carry your bundles if you carry me!”

By this point, I had decisively lost my looks: at seven I was a scrawny, buck-toothed gnome with a waxen complexion and a mullet, usually stalking around in pantaloons and a sunbonnet. Charlie, on the other hand, was still cherubic.

Sometimes I’d use his looks to my advantage; “Sing ‘Mister Golden Sun’,” I would hiss. And if it suited our joint interests—say, a buttered roll from the deli or maybe dinner in front of the TV—he would comply, breaking into a song he had learned at nursery school.

Oh, Mr. Sun, Sun, Mr. Golden Sun,
Please shine down on me.

Oh Mr. Sun, Sun, Mr. Golden Sun,
Hiding behind a tree

These little children are asking you
To please come out so we can play with you.

Oh Mr. Sun, Sun, Mr. Golden Sun,
Please shine down on,
Please shine down on,
Please shine down on me.

Needless to say, there were accompanying gestures—forming the rays of the sun with one’s arms—and all manner of mugging. It was revolting. It was electrifying. And it was deeply effective. Afterward, of course, we’d triumphantly bear our trays of macaroni and cheese upstairs to watch Fort Apacheor the Disney Robin Hood.

It seemed to me that Charlie got away with everything, and that his gall and mendacity knew no normal human bounds. Our parents were not especially strict—we spoke of families rumored to employ corporal punishment with hushed horror—but even by their standards, he was, I felt, indulged. Not that I wanted to get away with the same things. What use did I have for Legos or for being carried around the Affordables children’s thrift shop? I was furtive, certainly, but since what I was trying to conceal was usually, like, digging a root cellar, no one took much notice. In the depths of my heart, I admired him immensely.

As he aged, however, his manipulative tendencies began to approach bad-seed-level sociopathy. This came to a horrifying head when Charlie was about nine. We were in a crowded elevator in a Pennsylvania antiques mall. “You wouldn’t hit me here, would you, Mommy?” he said loudly. “Not in front of all these people!”

My mother went pale. Eyes turned on us in horror as my brother cowered in a corner, looking pathetic, while a malicious grin pulled at the corner of his mouth.

Was he getting some sort of obscure revenge? Had he been thwarted in some way—denied a trinket or a sweet? I’m not sure. Maybe it was a raw, arbitrary display of power.

Once we were safely free of the elevator—and the strangers had possibly gone to alert Child Protective Services—Charlie dissolved in hilarity and danced around with triumphant glee. My mom, deeply shaken, spoke to him sternly: that kind of thing isn’t a joke, people really dohurt their children, you could be taken away from us. When my dad appeared and she informed him of the events, the lecture was repeated. But then, Charlie had understood all that—why would he have bothered otherwise? And even then, I thought I glimpsed in my parents’ eyes a spark of horrified respect at the extent of his daring. Or maybe I was just projecting; maybe they were really scared.

Anyway, it’s now ascended into family legend. And it’s inappropriate for Father’s Day, maybe, but there it is.

Sadie Stein is contributing editor of The Paris Review, and the Daily’s correspondent.