While all the children learned a lesson that day, Sugar seems to have given the situation more in-depth thought. When Miss Moore asked the children for their thoughts on what they had experienced at the toy store, Sugar starts to make some insightful comments, but she is silenced by her domineering friend, Sylvia, who stands on her foot to get her to be quiet.

Sugar’s point was that democracy isn’t much good if it doesn’t mean “an equal crack at the dough.” By the equal crack, of course, she is referring to opportunities for financial advancement. After that sentence, whatever she may have been about to say next is silenced by her friend’s action, and it is at this point that Miss Moore looks at Sylvia with a look that appears to be sorrowful.

The reason for the sorrow in this look can only be because Miss Moore wanted to know more about what Sugar had learned that day, and whether the message that she wanted to impart with the children had sunk in. The whole point of Miss Moore’s decision to take these children on this excursion was in the hope that they would come to understand that there was more to the world than what they had experienced and that the world’s wealth was distributed incredibly unfairly. Miss Moore wanted to know what Sugar’s perspective on these matters was, and her sad look was in recognition of the fact that thanks to Sugar’s headstrong friend, her insights were to be lost.

In the short story "The Lesson" by Toni Cade Bambara, a woman named Miss Moore takes a group of African American children on an excursion to a toy store in a rich neighborhood. They enter the store and peruse the merchandise but are appalled by the exorbitant prices. The narrator, Sylvia, considers that the 35 dollars a simple clown toy costs could pay their rent, allow them to buy new bunk beds, or pay for a trip for the whole family to visit their relatives in the countryside.

This is obviously the comparison that Miss Moore wants the children to make. She wants to not only educate them on the value of money, but also help them to see the disparity between the lifestyles of the wasteful rich and others like themselves, who struggle for survival. The narrator, however, is in a rebellious stage of her life. We understand this from the beginning, when she states that

everyone was old and stupid or young and foolish and me and Sugar were the only ones just right.

At the end of the trip to the toy store, after they are back in their own neighborhood, Miss Moore wants the children to share their lessons. Despite Sylvia trying to shut her up by stepping on her foot, Sugar offers some genuine insight. She says that it's not much of a democracy if people don't have an equal share of the happiness. Sylvia steps on her foot again to prevent her from continuing, and this time Sugar remains quiet, although Miss Moore obviously wants to hear more.

She gives Sylvia the sad look because Sylvia prevents Sugar from finishing her thoughts about the situation. Miss Moore possibly wanted Sugar (or Sylvia) to come to the conclusion that they could overcome societal differences and succeed in life. She at least wanted the children to understand the reason why they visited the toy store: to understand the disparities in wealth in society. That's why she was disappointed when Sylvia didn't give Sugar a chance to finish.

At the end of Toni Cade Bambara's "The Lesson," Sylvia's friend Sugar voices what she has learned, much to Sylvia's disgust, and Miss Moore seems sad. Sylvia will control what she thinks and will not give anyone the satisfaction of knowing they have taught her anything...she resists letting Miss Moore drag her into the "lesson" she is trying to teach the youngsters on this "field trip."

"I think," say Sugar..."that this is not much of a democracy if you ask me. Equal chance to pursue happiness means an equal crack at the dough, don't it?" [...] Miss Moore looks at me, sorrowfully I'm thinkin. And somethin weird is going on, I can feel it in my chest.

Sylvia is a smart kid and...

...has the capacity to see the truth in things.

There truth is that the rich have so much that they can waste money on toys, when her family struggles to get by. Miss Moore realizes that something is going on in Sylvia's head:

You sound angry, Sylvia. Are you mad about something?

Miss Moore is right: Sylvia is mad about the inequity that Sugar expresses at the end. She thinks:

I'm mad, but I won't give [Miss Moore] that satisfaction.

Although Sylvia does not let Miss Moore know that the lesson was a success, the reader understands that Sylvia recognizes the inequity between her world and that of the wealthy—people that can afford a sailboat costing over a thousand dollars. We do not get the sense that she can act at that moment, but that she will not forget as she gets older and begins to navigate her way through a generation that will ultimately say, "Enough!" with the Civil Rights Movement of the 1960s.

[Sugar] can run if she want to and even faster. But ain't nobody gonna beat me at nuthin.

Sylvia understands how far-reaching the lesson is, though Sugar does not. Sylvia knows that the cost of toys demonstrates how democracy isn't working. However, Sylvia realizes that it's not enough to know about how unfair things are, but to do something about it. We can infer that Sylvia will do so as she gets older.