A school security officer smelled the smoke, then saw the cloud. Within minutes, he and a police detective were frisking a kid. Damon E. Cary watched as the two men uncovered several small bags of marijuana in the 17-year-old ninth-grader’s jeans. Quickly, Cary suspended the student. The detective charged him with possessing marijuana on school property.

On that April morning at Woodrow Wilson High, Cary had been managing chaos since before the first bell.

His day started with a group of riled students leaving a school bus and a girl crying. Then, a ninth-grader refused to get off a cell phone . She was slapped with a three-day suspension. Cary rescued her, sort of, by allowing her to come to school the next night for a program she’d been involved in for weeks.

In the hall, a ninth-grader approached. He feared that a fellow student was out to hurt him. Cary later summoned both boys. He presided as they talked out their differences, shook hands and agreed to not fight.

It was high noon, and there were still two hours left in the school day.

To Damon Cary, this first day of the last quarter at Wilson High seemed routine. He works at a school where about one in four students has dropped out.

Cary feels the weight of that stat. He knows the epicenter of the dropout problem at Wilson . It’s the ninth grade, the group he presides over as assistant principal. On average each year, about 300 new students enter the school as freshmen, joining about 200 repeating ninth-graders. In recent years, about four of every 10 freshmen fail.

Wilson’s students are urban, and its dropout problem cuts across race and gender . Most every kid who leaves comes from a non-traditional home, run by a grandparent, an aunt or an uncle, an older sibling, or a single parent – usually a woman with several children. In many cases, folks struggle financially.

Portsmouth’s other public high schools, I.C. Norcom and Churchland , also have dropout rates higher than Virginia’s 8.7 percent rate. But Wilson holds the distinction of having the second-worst rate in the state among regular high schools, surpassed only by Petersburg .

At Wilson, the staff plans to hold a retreat this month to assess what happened to this year’s ninth-graders: who made it out, who didn’t, and why.

Wilson Principal Timothy E. Johnson has been considering separating repeating ninth-graders from incoming freshmen. Cary also has been ruminating on ideas.

He is the guy Wilson’s ninth-graders seek out. Often, they meet with him in the cramped, cluttered office he keeps in the heart of the school’s humanities wing. He is a large man with a penchant for sharp suits. Students see the academic degrees on Cary’s wall and the supply of healthy food that helps him deal with his stressful job. In a deep, soft voice, he offers sober advice.

Joy Ellis snatched her son’s earphones from his head, and the lithe, long-haired 15-year-old stomped out of the main office. His mom yelled at him to come back.

Ellis was trying to reinstate Brandon. He was coming off a three-day, out-of-school suspension that Cary had issued for repeatedly being late to class. Ellis was not happy with the way Cary handled her son’s discipline.

Cary sometimes gives second chances to kids he knows, but for others he’s apt to follow disciplinary procedure. After Cary explained to Ellis that he went by the rule book with Brandon, he said, “I don’t know Brandon’s situation at all.”

That did it.

“You might want to pull his attendance record to try to find out!” Ellis retorted. “This kid is hell in a handbasket to get him to come to school. I get a suspension notice for three days? Well, guess what? This is exactly what he wants.”

Every chance he gets, Brandon has been skipping A lgebra 1, one of the courses a student must pass to become a 10th -grader.

His mother believes Brandon is smart but lazy, and here’s her evidence : He’s failing every course , including physical education.

She shared with Cary the dizzying story of her son’s academic path to Wilson. He skipped a grade at a private school because of his age. Then he arrived at Portsmouth’s William E. Waters Middle School in September 2008. He got suspended several times and was sent to an alternative center before being promoted to Wilson in early 2009.

At Wilson, Brandon was placed with a group of similarly overaged first-time ninth-graders who had had academic setbacks. Such students take most of their classes together and get special help with study and reading skills.

Even so, Brandon keeps skipping classes because schoolwork is “like, hard. So I can’t do it, so I don’t try to do it.”

The morning in the conference room, he slouched in a chair as his mother talked. Ellis knows her son is no angel.

“I’ll be the first to tell you he’s a pain in the butt.”

Cary asked Brandon whether he’s open to help.

“I don’t know if I can get help,” Brandon said. “I’m failing too much.”

“Right now, what do you want to be?” Cary implored.

Brandon’s mom answered for him. “He said he was happy to make $7 an hour working at McDonald’s!”

Brandon denied that, then admitted it was true, “until I find something better.”

Cary suggested that Brandon set his sights higher and told him all is not lost at school. “I can show you that you can still make it out on time in four years.”

Cary said he’d work up a blueprint for success and share it with Brandon the next day.

Morning came; Brandon skipped school.

Too many times, Cary has seen why students struggle to pass ninth grade.

He knows that, for many teens, it’s their first taste of autonomy in school. In some classes, they can pick up a rest room pass without asking a teacher’s permission and leave as the lesson continues. They’re responsible for getting themselves from one classroom to the next, which can be clear across the school.

The ninth grade is also when reading deficits can trip them up. Poor skills create problems in understanding a range of subjects, including math.

Unlike in the lower grades, ninth-grade students can’t be promoted because of their age. They’ve got to earn credits, and have a limited number of absences. Sometimes, when kids see they’re failing, they lose hope, so they stop trying.

Skipping class is a way to save face. Kids who perform poorly don’t want others to see that they’re behind.

Then there’s the simple fact that they’re still kids, many with notions of invincibility, naive about the consequences of their actions.

Some wind up out of school because they’ve “caught charges” and are serving time. Others may be put out for severe disciplinary problems or recommended to attend an alternative center, where they can work on GEDs.

For many others, the ninth grade becomes a revolving door they never exit, and they repeat it over and over until they become embarrassed to be among the oldest in class.

That’s why Cary worries about Kayla Spivey. At 16, she’s in the ninth grade for the second time and has already figured out she’s flunked again.

Kayla has skipped school repeatedly. It’s easy to leave Wilson and hide, with its dozens of doors and proximity to a neighborhood. Kayla and the crew she’s ditched school with like to ride around in a car, hang out at someone’s house, a fast-food restaurant and the Oceanfront.

Kayla has told Cary she’s bored, can’t stand her teachers, and some mornings, “I don’t feel like coming to school.” No amount of work at Wilson’s after-school program or Saturday classes will help her so late in the school year. Kayla’s skipping problem got so bad, a judge ordered her to stop ditching. To make sure she goes, her grandmother began driving her a few blocks up the street to Wilson. Kimberly Spivey, Kayla’s mom, can’t drive her. She works the day shift at a shipyard, where she makes about $10 an hour. The divorced mother is raising three children on her own.

Spivey, 35, wants to see her daughter finish high school and attend college.

Kayla sees an ally in Cary and calls him “awesome.” She believes he wants her to succeed.

Just last year, Kayla considered dropping out.

Lately, she’s told Cary she’s resolved to do better at Wilson next school year, when at age 17, she would be a freshman for the third time.

Cary is 37. He grew up in a middle-class African American household in Newport News. His education began as a toddler. His mother, a civil service clerk, and aunt, a second-grade teacher, constantly flashed him cards with vocabulary words and numbers. His aunt taught him cursive writing.

His older sister, his mother and his father – a department supervisor at a shipyard – all sat down for Sunday dinners, and Cary could talk to his parents about anything.

At Denbigh High School, Cary managed to be a “B-C student,” though he sometimes skipped classes and could be a cut-up and class clown. He never got a referral or a suspension. His dad’s brother taught drafting at the school and kept an eye on his nephew. Teachers would send Cary to his uncle, who’d give him a talking-to.

Despite the not-always-stellar behavior, Cary dreamed of being the first in his immediate family to earn a college degree.

In 1994, he attained a bachelor’s in business administration from Christopher Newport University.

That same year, he was working as a sales account executive for a newspaper in Richmond and read an article about the lack of African American male role models in positions of authority in public schools. It called to mind visits he’d made to his aunt’s second-grade classroom. He remembered how the children looked up to him in awe, and he liked the way that made him feel.

Cary decided he wanted to make education a career. He wanted to inspire young black men.

The next year, he began substitute teaching in Newport News Public Schools. By fall, he began working as an in-school suspension coordinator for one of the city’s middle schools.

Finally, in 1996, with teaching certifications in hand, he became a full-time instructor. He taught middle school math and science and eventually civics.

Over the years, he earned three more degrees, including, in 2006 – the year he arrived at Wilson – a doctorate in education. He liked the idea that it might impress some kids, thinking his role as a doctorate-wielding assistant principal “may be the only chance a kid can see a black doctor without being sick.”

Cary’s worries now go beyond just young black males. He wants to help kids, period.

Jasmine Smith was someone Cary didn’t have to fret over. At 14, the first-time ninth-grader had been a decent student. That changed after Jasmine left school in January to have her baby.

While she recovered and took care of her daughter, she did her schoolwork. But her grades slipped.

Cary knows that Jasmine’s mother, Karen Smith, pushes Jasmine to succeed. Smith was disappointed by the pregnancy. She understands the consequences.

Smith , who is 30, had Jasmine when she was 15. Not long after Jasmine, she had her second child. Only after dropping out and then back in a few times did she graduate from a North Carolina high school at age 20. A school guidance counselor stayed on her, telling her she could achieve great things.

It was the first time Smith remembered anyone ever pulling for her.

A high school diploma is Smith’s highest academic achievement. She went on to hold a series of jobs, including operating a fork lift, working in a factory, putting the fifth wheel on trucks. At times, she and her family, which now includes a third child, have bounced around Portsmouth, from a sister’s house, to her parents’ home and a homeless shelter.

Her family’s instability has saddened Jasmine. She also wishes her father was still alive. He died of an enlarged heart at age 16, when she wasn’t quite 6 months old.

A few months before Jasmine gave birth, her mother landed a steady job assisting the mentally challenged. She still works there.

Smith and a sister split the $975 monthly rent for a two-story duplex in Prentis Place, where, a month after the move-in, most everyone is sleeping on inflatable beds designed for camping. Jasmine and

a 10-year-old cousin share one of the beds, across from the bassinet her daughter sleeps in. Smith, who aims to earn

an associate’s degree before she’s 35, has told Jasmine she has no choice but to graduate from high school. She doesn’t want her daughter living “paycheck to paycheck to paycheck.”

But since Jasmine had the baby, her B and C grades have fallen . Her mother and other adults in the house, including Smith’s boyfriend, take care of the baby when Jasmine’s at school. But when Jasmine comes home, she’s the full-time mom.

She’s considered dropping out of school.

But then Jasmine thinks about her mother, her baby and her late father; she wants to do better.

That’s why, one afternoon, she made a trip to Cary’s office. She wanted his advice on how to get her grades up. She wants to attend Hampton University, and maybe go on to become a pediatrician.

Cary looked directly at her.

“I have something in common with you,” he said. A moment passed. “I had a child when I was 16.”

Jasmine’s dark brown eyes took in Cary. She was leaning forward. She listened.

Cary explained that after his daughter arrived, he had to stop running track and couldn’t go to football games as often as he had. He shared the responsibilities of raising his daughter with his girlfriend, and then for some years, raised her pretty much on his own, with his parents’ help, until she was 8. By then, he was only 24.

Cary told Jasmine she can be a doctor. She’ll need to stay in school, go to college, get the right degrees.

He’ll show her how she can finish high school. His door will always be open.