The first time I met him, I was a tangled-haired adolescent in a public school system that, like the country itself, was teetering on the edge of self-immolation. The United States had endured three mind-numbing political assassinations in the preceding six years. 30,000 American men and a few women, mostly under 22, had lost their lives in Southeast Asia. A disheartening fragmentation of the Civil Rights Movement had occurred not long after a few militants had broken away from SNCC and formed the Black Panthers. Lastly, an incipient division between parents and children formed that had so troubled Time Magazine that it had spent an entire issue on something called “The Generation Gap.” By 1969, when I formally met Holden Caulfield for the first time, cynicism and mistrust had already formed the bookends of a new societal order.

Frankly, I don’t remember much about my first reading of The Catcher in the Rye except that we freshmen adored his skepticism, droll wit, and inimitability. Holden seemed to us like a rainbow in the night, a kindred spirit for our quirky era. When my teacher asked me for my opinion of young Caulfield after we completed the novel, I leaned on the back legs of a chair and glanced out at the majestic elm trees that framed Donizetti Street. In an unmistakably smart-alecky voice, I replied, “Holden? He kills me.”

My Wellesley, Massachusetts Junior High School English instructor at the time was not amused.

Not until 25 years later, when I began teaching J. D. Salinger’s The Catcher in the Rye, did the enigmatic quintessence of Holden Caulfield finally capture my heart. Still, that would take some time. As a matter of fact, when I initially instructed “Catcher” with my ninth-grade class in Greenwich, Connecticut, I perceived that Holden was a self-absorbed, spoiled adolescent who needed his ass kicked. After all, I was 40, with two kids, and not some egocentric teenager anymore.

Political columnist George Will would later compose a generational epitaph for young Caulfield in a much-admired column for The Washington Post. He began by quoting Holden’s first-person narrative, and then the acclaimed essayist used a billy club to knock the young man off of his iconic pedestal:

“If you really want to hear about it, the first thing you’ll probably want to know is where I was born, and what my lousy childhood was like, and how my parents were occupied and all before they had me, and all that David Copperfield kind of crap, but I don’t feel like going into it, if you want to know the truth”.

“With those words,” wrote George Will, “16-year-old Holden Caulfield slouched into American life fifty years ago this month. He felt entitled to feel quite sorry for himself. His feelings fascinated him, and his creator, J. D. Salinger, believed that readers should sympathize with them. By now, many millions of them have. Holden was a new social type that subsequently has become familiar — the American as a whiner.”

When I began my first class on The Catcher in the Rye 25 years ago this month, I had at least one foot in Mr. Will’s camp. Today, I am unconditionally in Holden’s corner. Still, as my ninth-graders settled into their seats one chilly October morning in 1995 to begin their formal study of Salinger’s novel, I kept my opinions to myself. In my 15th year in the classroom then, I knew by then that while the best teachers steer their students toward shore, it is up to them to land on firm ground.

Because my charges had read and loved Harper Lee’s To Kill a Mockingbird the previous spring, I reminded them to recall Atticus Finch’s advice to Scout as they began to scrutinize Holden Caulfield. “You never really understand a person until you consider things from his point of view […] until you climb into his skin and walk around in it.” Atticus’s axiom inevitably became a mantra for my class as we explored the inner workings of young Mr. Caulfield.

When I handed out a copy of the book to each student, my scholars were surprised to examine the book’s unique cover, which, at the time, was blood red with white lettering. To their bewilderment, no advertising of any form was included on either the front or back of the paperback. “I guess the book stands on its own?” inquired one perceptive pupil when she began fingering the paperback.

Just before the kids opened to the first page, I compared The Catcher in the Rye to Twain’s Adventures of Huckleberry Finn – a novel the children had previously read. “In both cases,” I exclaimed, “the protagonist is on a journey of self-discovery that will surprise and challenge the most prodigious of readers.”

We then had some fun breaking down the first three paragraphs of the book. As Holden begins to converse with the reader on page 1, most readers assume that his riveting, stream-of-consciousness monologues are powerful examples of “first-person narration.” However, twice during the manuscript, he clearly refers to “this place,” which turns out to be an unnamed asylum south of Los Angeles. As we soon discover, Holden is recovering from near-tubercular symptoms and a nervous breakdown he suffered the previous December back East. When the narrative opens six weeks later, it is early February 1950, and he is recovering from a physical and emotional malaise that nearly killed him.

When Holden then used the word, you, twice in the novel, my class speculated that he was conversing with a psychotherapist in the asylum. They further perceived that virtually every chapter in the book is similar in structure and length. “Could each chapter represent 26 therapeutic sessions?” asked a particularly enterprising boy one day in class.

By the end of Chapter 1, my students realized that Holden never gave in to telling us much at all. By employing the duality of dramatic irony and “showing” instead of telling, Salinger’s seductively easy prose turned out to be as complex as Joyce or Faulkner’s. Ultimately, we all had to dig, dig, dig. The kids perceived that the book’s subtlety lay in the spaces in-between. As easy as the language appeared to be, the lazy reader would accept Holden’s lethargy and querulous nature as fact. “There’s much more to this character than what he tells you,” offered a conspicuously deft girl one day in a group discussion.  

As my class soon discovered, the shocking death of Holden’s beloved younger brother had acted like an overpowering nor’easter that left him rootless and paralyzed. When Allie Caulfield suddenly died of leukemia in July 1946, in their summer house in Maine, the solid floor that had held Holden together beforehand collapsed in a heap. When Holden then matter-of-factly mentions that he punched out every window in his parents’ garage after being informed of his little sibling’s passing, the kids’ antennae were instantly raised. One sagacious student later wrote, “Holden characteristically punishes himself – and no one else – for Allie’s death. From then on, he seems paralyzed by grief. He can’t seem to move past it due to confusion, grief, and loyalty to Allie.”

Another scholar keenly observed, “The key to the story lies in Allie Caulfield. He died at 12, still innocent and evolving, and he remains that way to Holden after that. Not only is Allie stuck in time, but so is Holden. He can’t move on in life. It’s sad, and it’s completely understandable.”

By the second week of our focus on “Catcher,” Holden’s memorable sense of language kidnaped the attention of the vast majority of the students. His “smells-like-teenage-spirit” kind of narration was a mini-lesson in mid-twentieth-century adolescent colloquialisms. Words like backasswards, vomity, and expressions such as “strictly for the birds” and “it kills me” became catchwords and phrases for many of my pupils once they read the book.

As my class continued to zero in on Holden’s issues, they realized that one of his more significant problems was understandably undiagnosed in the novel. After all, a more psychologically savvy student body could see what we left largely untouched a generation previously. “It seems that Holden suffers from undiagnosed ADD. He is obviously distracted, enormously bright, and unfocused,” detected a student keenly one day. Another pupil then chimed in: “Holden is probably an obsessive-compulsive personality who is driven crazy by everything from “phonies” to the way people use the expression, good luck.”

Over the course of the next few weeks, the kids in my class invariably walked in the shoes of Holden. They understood Holden’s obsession with the ducks in Central Park in the winter was nothing less than a projected kind of universal teenage plea, “What will happen to me?” The class laughed at the phoniness of the call girl, Faith Cavendish, who is suddenly impressed that Holden purportedly attends Princeton. My kiddies were stirred when Holden decided not to throw a snowball at a fire hydrant at his old boarding school because it subconsciously represented the innocence that Holden wanted to protect. They nodded their heads in agreement when Holden criticized such words as grand for being too imprecise. As one student sagely wrote, “Holden preferred words that were carved out in granite – not quicksand!”

My class seemed transfixed when Holden talked about his enduring love for the Early Americas Exhibit at the Museum of Natural History. When he admitted, “The best thing, though, in that museum was that everything always stayed right where it was. The only thing that ever changed was you,” they understood that in a capricious world, Holden was trying to hold onto everything good. The students were astonished when Holden admitted that when a girl said to stop while they engaged in foreplay – he actually stopped. To someone who was already confused by the nuances of sex, Holden’s confusion with “the game” accurately mirrored every group of adolescents I have ever taught.

However, the enduring theme of The Catcher in the Rye that most moved my class was the conundrum of adolescence. They came to recognize the struggle that readers of the novel poignantly endure from childhood to adulthood. Eventually, everyone has had to leave the secure cocoon of innocence to enter the duality of cynicism and experience that frames adolescence and adulthood. For them, this has always had prodigious connotations – from self-worth to sex to the most prevailing question for someone that age, “What will I do for the rest of my life?” This voyage of self-discovery became the wellspring for the next handful of class discussions. One particularly nimble pupil wrote in a subsequent reflection piece: “This is the almost fatal connection that you make with Holden if you read the book as a teenager. You begin to ask questions that have no answers. It is up to you to uncover them; it might take a lifetime to do so. There is no time clock for maturity.”

My students became absorbed with a matter-of-fact anecdote that Holden includes in Chapter 16. When Holden observes “a little kid” merrily skipping to the tune of “if a body catch a body coming through the rye,” the class understood that they had stumbled onto something enormous. As the kids ascertained, Holden has just been reminded about all the good that childhood has invariably represented to him, which is embodied in that frolicking, whirring young boy.

Later on, when his remarkably perceptive younger sister, Phoebe, asks him what he would like to do in the future, Holden’s rejoinder became food for thought for my students. “I keep picturing all these little kids playing some game in this big field of rye and all. Thousands of little kids and nobody’s around — nobody big, I mean — except me. And I’m standing on the edge of some crazy cliff. What I have to do, I have to catch everybody if they start to go over the cliff — I mean if they’re running, and they don’t look where they’re going I have to come out from somewhere and catch them. That’s all I’d do all day. I’d just be the catcher in the rye and all.”

When I read the above passage on a windswept November morning, one of my pupils, the oldest child in a family of four, put his head down on his desk and began sobbing. As Holden would say, “You had to be there.”

After the kids had begun to discuss Holden’s desire to protect the innocent and the “have-nots” of the world, on an impulse, I played the 1960’s anthem, “Chimes of Freedom.” Through Bob Dylan’s unambiguous verses, a mighty bell tolls for every kind of damaged person he could conjure up. “Tolling for the aching ones whose wounds cannot be nursed,” a defiant Dylan sings. “For the countless confused, accused, misused, strung-out ones and worse/And for every hung-up person in the whole wide universe/And we gazed upon the chimes of freedom flashing.” When the ballad concluded, each student sat motionless in his or her seat, soaking in the bittersweet anguish that framed Dylan’s work.

At this critical juncture of the narrative, Salinger focuses on a before-mentioned character, Holden’s youngest sibling, 10-year-old Phoebe, whose guileless and compassionate shadow looms over the rest of the novel. The prototype for Holden’s image of childhood – innocent, bright, engaging, and spontaneous – she brightens the dreariness of Holden’s existence like a lighthouse beacon. My class loved Holden’s unspoiled physical description of Phoebe in Chapter 10: “She’s quite skinny, like me, but nice skinny. Roller-skate skinny.” Nearly every kid in the class emphatically raised their hands when I asked them, “Is there someone similar to this vibrant little girl in your family?”

Phoebe, who is both discerning and curious, has witnessed one of her brothers perish of cancer while another has since languished to the point of a mental breakdown. When Holden secretly visits her in their Central Park West townhouse, he has just been booted out of his fourth school in three years. She is wise beyond her years, yet “old Phoebe” intuitively realizes that Holden is in serious trouble.

Thus, when her older brother purchases a record for her and then inadvertently smashes it to pieces when he drunkenly falls in Central Park, it becomes a confidence crisis for both Caulfield children. “If I were Holden,” admitted one boy after reading about the record-smashing incident, “I would have thrown the broken pieces away. Most anyone would.”

Not Holden.

Thus, when he gives Phoebe his shattered gift to her, she lovingly accepts the pieces of the broken record from him. The same pupil returned the next day and said that his original inclination had been wrong. “I guess, Mr. K., that by accepting his broken record, Phoebe is also completely accepting Holden for who he truly is at the time, which is all broken up – and in pieces.” Another student chimed in, “She accepts and loves Holden unconditionally. Phoebe loves him with all of his flaws despite the fact that he’s left everyone down, especially himself.”

When Holden then visits Phoebe’s elementary school to inform her that he’s leaving New York City for good, he observes three scrawled fuck yous in separate areas of the school. These written epithets harken back to the “catcher in the rye” theme, which causes Holden to turn bright red. In his fury, he tries to scratch out the phrase that seems to have been written in the bathroom of Phoebe’s school with the same kind of bravado as a Times Square news ticker. After seeing a second and then a third “fuck you” during his visit, Holden finally comprehends that he cannot erase every swear word he sees in life. Ultimately, he simply can’t be the “catcher in the rye” for others. As nearly every student grasps by this time, however, there is one person Holden does need to save. Himself.

In the climactic scene at the famed carousel ride in Central Park that concludes the novel, Holden has a revelation that might actually save him. As Phoebe climbs aboard the carousel, he then sees his beloved sister’s luminous face shimmering like a jewel as she goes around and around. Suddenly, Holden realizes that her overriding love for him is enduring. Holden suddenly has an epiphany. Phoebe, the quintessential symbol of innocence, must grow up – completely unfettered. She needs to reach for the proverbial brass ring and follow wherever her personal journey takes her down the road. By extension, Holden also needs to grow up. Ultimately, he discovers that if he has a few people, such as Phoebe, his life might be worth it. As the scene concludes, we, the readers, are reminded that love is comparable to the air we breathe. You can’t see it, but you can surely feel it.

After more than two decades of looking at life through the extraordinary lens of Holden, I have not only come to understand him, but I now realize that “the chimes of freedom” toll for everyone. Like my literary friend, young Caulfield, I now know that while we are all deeply flawed, there is so much to cherish in most people if you give them a chance. As one adroit student wrote to conclude the unit: “It’s uplifting to realize that if you stumble in life, there will probably be someone there to pick you up as you would for them. Maybe we’re really ‘catchers in the rye’ for one another.”

In a life that often disappoints, love defines us, gives us meaning, and motivates us through the good and bad times. Love is our one constant. Love is our North Star.

(The famed carousel ride at Central Park in 2019. Every time I visit it, it kills me).

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