week, that’s a yellow in academic preparedness. If she has an open case with her college’s counseling service, that’s a red in socio-emotional wellness. If she “has great difficulty in taking responsibility and completing important tasks,” that’s a red in noncognitive preparedness. From her desk at any time, Dowling can access a database that displays a glowing red dot for each potential problem area of every student her advisers are working with.

Reading through the playbook on the subway back uptown reminded me how complicated the logistics of success can be. The book is packed with facts and ideas—deadlines for financial-aid forms, notes on picking majors, tips on improving study habits, suggestions for good relations with roommates and professors—information that students who graduate from Riverdale have heard from parents and friends and older siblings for years already, that they’ve been immersed in, in fact, their whole lives. To KIPP graduates, though, it often feels like a foreign language.

Here’s one way of looking at character: It can function as a substitute for the social safety net that students at Riverdale enjoy—the support from their families and schools and culture that protects them from the consequences of occasional detours and mistakes and bad decisions. If you don’t have that kind of safety net—and children in low-income families almost by definition do not—you need to compensate in another way. To succeed, you need more grit, more social intelligence, more self-control than wealthier kids. Developing that strength takes a lot of work. But for the KIPP students who do manage to find those skills, who are able to make it through that minefield and graduate from college, it’s hard not to think that they will set out into adulthood with some real advantages over their Riverdale counterparts. Not financial advantages, but character advantages. When a KIPP student graduates from college, he will have not only a BA but also something more valuable: the knowledge that he climbed a mountain to get it.

3. How to Think

1. Sebastian’s Blunder

Sebastian Garcia couldn’t figure out where he’d gone wrong. One minute he was up by a bishop and a pawn, in good position, feeling strong, looking to start off the 2011 National Junior High Chess Championships with a victory. And the next minute he was in deep trouble, his advantage squandered, his king scurrying across the board like a frightened little mouse, fleeing his opponent’s rook. A few moves later, when his defeat was complete, Sebastian limply shook hands with the boy who had beaten him, a sandy-haired kid from a central Ohio suburb, shuffled his way through the cavernous convention-center ballroom where a thousand heads were bowed over chessboards, and slunk back to Union B, the windowless conference room down the hall that was his chess team’s temporary home. Sebastian, a short, stocky, quiet Latino with round cheeks and a thick bristle of black hair, was in the sixth grade at Intermediate School 318 in Brooklyn, and two days earlier, along with sixty teammates and a handful of teachers and parents, he had traveled eleven hours in a chartered bus to Columbus, Ohio, for a few days of competitive chess. His weekend was not off to a good start.

The ritual for students on the IS 318 team was that, win or lose, after each game they would come back to the team room for a postmortem with the school’s chess teacher, Elizabeth Spiegel. Sebastian slouched into Union B and approached the small table where Spiegel, tall and slender, sat behind a chessboard.

“I lost,” he announced.

“Tell me about your game,” Spiegel said. She was in her mid-thirties, dressed all in black, her pale skin made paler by the contrast with her brightly dyed hair, which changed hues somewhat from season to season. For this tournament, she had chosen the deep vermilion of red velvet cake. Sebastian dropped into the chair opposite her and handed her his chess notation book, where he’d scrawled all sixty-five of his moves as well as all of his opponent’s.

The other guy was simply better than him, Sebastian explained. “He had good skills,” he said, a little plaintively. “Good strategies.”

“Well, let’s see,” said Spiegel, and she took the white pieces and started re-creating the game on the board between them, making each of Sebastian’s opponent’s moves while Sebastian, as black, replayed his own moves. Sebastian and the Ohio boy had both begun by bringing out a couple of pawns, and white quickly developed his knights, a standard opening called the Caro-Kann, which they’d gone over in chess class back in Brooklyn dozens of times. And then the Ohio boy had pulled one knight back to an unexpected square, so that both of his knights were attacking a single black pawn. Sebastian, nervous, moved another pawn up to defend, but he had stumbled into a trap. His opponent quickly swooped a knight down to capture the defending pawn, and just four moves into the game, Sebastian was down a piece.

Spiegel stared at Sebastian. “How long did you spend on that move?” she asked.

“Two seconds.”

Spiegel’s face grew cloudy. “We did not bring you here so that you could spend two seconds on a move,” she said, a steely edge in her voice. Sebastian looked down. “Sebastian!” He looked up. “This is pathetic. If you continue to play like this, I’m going to withdraw you from the tournament, and you can just sit here with your head down for the rest of the weekend. Two seconds is not slow enough.” Her voice softened a little. “Look, if you make a mistake, that’s okay. But you do something without even thinking about it? That’s not okay. I’m very, very, very upset to be seeing such a careless and thoughtless game.”

And then as quickly as the storm had arrived, it passed, and Spiegel was back to moving pieces and examining Sebastian’s game. “Nice,” she said as he avoided a pawn capture. “Very clever,” she said when he took his opponent’s knight. They went on like this, move after move, Spiegel praising Sebastian’s good ideas, asking him to come up with alternatives to his less-good ones, and again and again reminding him that he had to slow down. “You were playing in some ways an excellent game,” she told him, “and then once in a while you moved superfast and you did something really stupid. If you can stop doing that, you’re going to do very, very well.”

I first met Spiegel in the winter of 2009, after I read an article in the New York Times about her team’s performance at the National Scholastic K?12 Championship the previous December. The article, by the paper’s chess columnist, Dylan McClain, pointed out that IS 318 was in the federal education department’s Title I program, meaning that more than 60 percent of the students at the school were from low-income families, and yet at the tournament in question, Spiegel’s students had beaten wealthy kids from private schools and magnet schools. I was intrigued, but to be honest, I was also a little skeptical. Hollywood producers and magazine editors love tales of inner-city kids defeating private-school students in chess tournaments, but often, when you look a little more closely at the triumphs, they aren’t quite as inspiring as they originally seemed. Sometimes the tournament that the team from the disadvantaged neighborhood won turns out to be a minor one, or the division that the students were competing in was restricted to students below a certain ability rating. Or the low-income kids turn out to be somehow atypical—they go to a selective school with an entrance exam, or they’re recent immigrants from Asia or Eastern Europe rather than black or Latino kids from families with long poverty histories. In 2005, to give one example, New York magazine ran a long, adulatory profile of the chess team from the Mott Hall School, known as the Dark Knights of Harlem, “a hard- charging bunch of 10-to-12-year-olds from Washington Heights, Inwood, and Harlem” who were competing in a national tournament in Nashville. They did come in second in their division of the sixth-grade tournament, which was a fine achievement—but they were competing in the under-1000 section, meaning they didn’t play anybody with a rating over 1000, which is fairly low. And the students had all had to pass an entrance exam to get into Mott Hall, so they were above average to begin with. Plus the team, while technically from Harlem, had only one black player; almost all the others were immigrants born in Kosovo or Poland or Mexico or Ecuador or China.

And so when I showed up at IS 318 on a January morning, I expected to encounter some comparable asterisk. But I couldn’t find one. The team is diverse—there are a handful of whites and Asians—but most of the players are black or Hispanic, and the best players are African American. Few students on the team, from what I could tell, faced quite the daunting array of disadvantages and obstacles that the average student at Fenger High School in Roseland did, but with 87 percent of IS 318’s students eligible for federal lunch subsidies, the school had

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