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Sperber Award Speech May 2008: The Tao of Bob
When I arrived to teach at Brookline High in the fall of 1990, Bob was beginning his second year as Assistant Headmaster. Frankly, I was too busy and too new to pay much attention to him. However, I could feel a palpable difference when, two years later, he took over as Acting Headmaster. If truth be told, at first the change was a tad jarring. We had gone from a rather distant leader to this bearded guy from Queens, roaming the halls, announcing that Brookline High School was the best high school, not in the state, not in the country, but in the cosmos.
Let me set thc scene further. Although I was a few years out of college, I was still in the thrall of my intellectual heroes. For example, I had been seduced by Dostoevsky’s Underground Man, a highly educated fellow who, from his Hamlet-like existential paralysis, said, “men of action are active just because they are stupid and limited.” I felt at home at Brookline because I found many colleagues of a similar disposition: hypereducated, a tad cynical, and interested in the life of the MIND.
And here comes this guy in cowboy boots, hugging people in the halls.
Needless to say, Bob’s exuberant cheerleading was at first met with skepticism. As a school we were better known for our cool and distant irony than our pom-pom-waving. Who was this guy? Wasn’t he a little, well, MUCH? Why was he always so darned cheerful? Why was he suddenly appearing everywhere at once: in the classrooms, offices, hallways? Why didn’t he sit down?
Fortunately, our “cool” had no dampening effect on Bob’s passion. It took a couple of years for us to realize that this headmaster wasn’t just talking a big game. Here is what we came to see: Bob Weintraub is a man of action. He works harder and longer, week after week, year after year, than anyone else in the building (and that’s going some). And at home after midnight, when he finishes writing a proposal for a new initiative, or correcting a set of freshman papers, or writing a note to a sick colleague, he picks up the BHS Yearbook before bed so he can memorize more student names.
Bob gets things done because he recognizes and hires talented people who love kids. He gets things done because he understands politics -- which he once defined to me as “the means by which a group finds out what it believes,” a definition which took the legs right out from under my cynicism. He gets things done because he has a vision: not just “freedom and responsibility,” but a vision of academic integrity, of civic involvement, of pride in hard work, of acceptance of human imperfection, and of aggressive optimism... what I now call “Bobtimism.”
And despite what Dostoevsky’s Underground Man said, this man of action was anything but “stupid and limited.”
Elon Fischer remembers that when he arrived here after teaching at another high school, he was astounded by the high level of discussion at the first faculty meeting. He could see this tone came from Bob, who begins every school year with quotations from the greats: Kierkegaard, Schlesinger, Jim Walsh, Mike Frantz. This year, using a passage from Saint-Exupery, Bob urged the staff not just to give orders and assign boatbuilding tasks, but to teach our students to “yearn for the vast and endless sea.” In this way and others, Bob encourages deep thinking and a high level of discussion --which in turn allows us to grapple with major educational challenges. As Elon says, “Bob is always looking up. Sitting around and not changing anything is not an option.” If you work for Bob, you, too, “yearn for the vast and endless sea,” and you throw yourself into building the boat to get there.
As a result, sixteen years later, under Bob’s leadership, Brookline High is a much stronger, more unified school. We have maintained the highest academic standards, while becoming a more human, dynamic place. From his first days as Headmaster, he has preached the importance of each student’s having a strong relationship with at least one adult in the building. Bob infuses everything he does with his belief in the power of relationship.
The students, parents and staff now know and trust him. His alert and flexible intelligence makes him adept in the insanely varied situations a typical school day throws at him. His courage and confidence allow him to make tough decisions, to stand up to people who disagree with him, and to take risks when he knows the results for students will be worth it. His boyish sense of humor allows him to recognize absurdity wherever it lies, putting problems constantly in perspective instead of letting them overwhelm us.
Bob often cites Oliver Wendell Holmes’ desire to find “simplicity on the other side of complexity.” Bob believes in working through complex problems, not around them. Being Big Daddy to over 2000 adults and teenagers is, for most mortals, a crushing job, demanding varied skills, and Bob’s success as teacher, policy-maker, disciplinarian, event coordinator, chief strategist, guru, father confessor, trash picker upper, is difficult to set down in any space. What I can say is that the Underground Man was paralyzed by complexity. Bob Weintraub is energized by it. He seems to be most fully himself, most fully alive when in the midst of crisis. He gives off this perverse glow.
If I were going to reach simplicity on the other side of the complexity of Bob -- in other words attempt to uncover the “Tao of Bob,” I would venture that what most makes Bob such a powerful leader is his inexhaustible, irrational joy in existence. Bob Weintraub loves people, he loves life, and, indeed, he loves education because it’s the best way he knows to gather kids together and swing open the doors to that life he loves.
Luckily for all of us and for this school, his warm spirit is contagious. Luckily for me, Bob has become not just a mentor, but a close friend. More than any other single person, he is responsible for BHS feeling like HOME to me. On a bad day all it takes is five minutes with Bob in the cafeteria or outside on the steps after school or in his office (eating his candy), and suddenly, my job seems, well, like FUN. IMPORTANT fun. Why would I want to do anything else?
I hope this speech communicates some small part of my enormous respect, gratitude, and affection for our Guest of Honor. Bob, I always joke with you that I work hard in order to make you look good. All I can say is: first, I’m only half-joking. Second... look, my work seems to be paying off!
One day a couple of years back I walked into the Atrium, and there, in the middle of the marble lobby, stood a huge paper mache sculpture of Bob Weintraub. BHS art students had created it and had installed it in secret the night before. The sculpture was a loving portrayal of Bob, capturing his ear-to-ear grin, his glasses, his crazy tie, his perpetual motion. Yes, I immediately thought. Bob is the kind of leader, here at the best school in the cosmos, who gets and deserves a statue before he’s even dead.
Yes, I am thinking now. He also deserves the Sperber Award.
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