Mary Jacobson knows that the Red Sox took a beating last week from the Arizona Diamondbacks. She also knows that if you're teaching math to a second-grade boy, it's not a bad idea to throw in some baseball talk.

What's surprising about all this is that Miss Jacobson is not some whippersnapper fresh from college. On the teaching faculty at the West Tisbury School, she's senior staff, just days away from putting the cap on her last felt-tipped marker after 33 years working in Vineyard schools.

By the time some teachers hit such a milestone, they've already been dead wood for a long time. Not Miss Jacobson.

When she rounds the corner of the desk in her office, a boy and a girl are waiting for her.

"Hi dearies, how are you?" she says. The girl, a first-grader with a bandaged elbow, leans into the middle of Miss Jacobson's bright red jumper for a hug.

The moment is more than the embrace. The girl, who was sitting huddled on the floor just a minute before, is now grinning in Miss Jacobson's presence.

It's Wednesday morning on the last full week of school, a week given over to field trips to the beach or the Flying Horses. But Miss Jacobson, a special needs teacher, is ready for math, and there are no arguments from her two students.

"Is eight plus eight 16?" asks the girl who has parked herself at the computer to work through a math software game called Number Maze.

"Yes," says Miss Jacobson. "It's one of those double number things that's so cool to know."

Miss Jacobson has an easy knack for talking to kids without sounding phony or condescending. "Did you plot your approach to the castle?" she asks the girl who is navigating the maze.

More often than not, her words are laced with encouragement and promise. You're smart, she tells them. You're mathematicians. This will be "a piece of cake," she says.

It's no surprise that colleagues have recognized Miss Jacobson's special gifts, but it's interesting to note that the praise doesn't touch on any of the current buzzwords of education in this era of high-stakes testing. As Miss Jacobson bows out of the classroom, she's being remembered not for helping to crank out top test scores, but for her humanism as a teacher.

"She's very loving and accepting, and that's how she makes people feel of any age," says Jill Rosenkranz, a special needs teacher at the Chilmark School.

From 1975 to 1990, Miss Jacobson was the teaching principal in Chilmark. For most of those years, it was a two-room schoolhouse with about three dozen students in first through sixth grades.

Eleanor Neubert, a teaching assistant in Chilmark for the last 26 years, recalls Miss Jacobson's tenure as characterized by an intentional lack of bureaucracy.

"It was when Chilmark was still a very small town and we weren't very many back then," said Ms. Neubert. "Her main focus was on those children. She loved teaching."

In Chilmark, Miss Jacobson came to be known as Miss J. "That developed because the first-graders couldn't say Jacobson. It came out Jack-so-pin," she says.

What she loved about her time in Chilmark was the chance to teach children over such a stretch of years. "One of the things I was most blessed with was the continuity of children over time," she says. "As a teacher, that is a wonderful gift to see the development and acquisition of skills."

Miss Jacobson comes from a family of teachers. "The thought that I would do anything else was unheard of," she says.

She grew up outside Chicago but attended college in a small town in Kansas. In 1967, she signed up for the Teacher Corps, a federal program similar to the domestic Peace Corps. Her assignment landed her in an elementary school on Chicago's south side.

Her students and her colleagues were all black. "It was right in the middle of the Civil Rights era," she says. "In '68 when Martin Luther King was assassinated, it was a Thursday. We all had to go to school on that Friday. That night, driving up north to my parents in Wilmette, I was watching Chicago burning."

In 1969, Miss Jacobson set out for Boston, intent on working in another inner-city school, but amazingly, there were no jobs there. An ad in the state Department of Education posted an opening at the Oak Bluffs School for a special needs teacher.

Coming to the Island from the city, she wondered at first if she would stay more than a couple years. But Miss Jacobson found she could plug into the community here. She found Grace Church and she found the stage.

"You have the opportunity to participate in the life of the Vineyard," she says. "If you choose to, you can become a real part of the community. It's fun to be part of a lively place."

Whether it was singing the Messiah or acting the part of Mother Superior in Nunsense, Miss Jacobson reveled in the cross-pollination that took place on the Island.

"Duncan Ross at the high school had this idea to do a musical with community members and high school students. We did Carousel that year," she says. "It was like watching the movie Jaws. All these people you know on the street are now in this play."

Miss Jacobson is a soprano. "Although it's dropping," she says. "Those high As aren't the way they used to be."

Laughter comes easily to Miss Jacobson. Friends say that one of her favorite phrases is, "It's going to be so much fun."

Indeed, while she makes things look easy and fun, Miss Jacobson's desk tells another story. It's where she refuels. A bowl of cereal covered in cellophane sits there, as does a plastic bag of trail mix.

"This is one of those places where you have to graze all day," she says. "You have to be ready for action."

Even with retirement looming, Miss Jacobson is ready for action. She'll spend part of the year back in Wilmette, helping care for her 87-year-old mother and 94-year-old aunt. Still, she says, "My family is there, but my life is here."

But the prospect of closing the last book on a teaching career is clearly emotional. "I can be walking down the hall, and it will just come over me. To be a part of a daily community in a school is so much fun. It's busy and demanding, but it can be a very sweet experience. That's what mine has been," she says as tears form in her eyes.

When she came here, she recalls, the Island had one restaurant and a movie theatre that was open for only six weeks.

"It's very difficult to think of that final day when there won't be a reason to come back here. It goes by so fast. Three decades," she says. "How fortunate to spend them on the Vineyard."