Ki Tavo 5786: Follow the Leader

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August 23, 2026

10 min read

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Ki Tavo (Deuteronomy 26:1-29:8)

GOOD MORNING! Ah, August – that very special month that brings vacations to a close as it ushers in the new school year. It is a time of new beginnings and exciting possibilities.

Did you ever notice the throngs of mothers at a bus stop tearfully sending their precious children off on their first day of school? Did you think those were tears of sadness and longing? Hardly. It is the heart’s silent, involuntary confession that it has just witnessed something beautifully transcendent; namely, that for the first time in two months, their child is someone else’s problem for the next eight hours.

I am reminded of the following story: A mother repeatedly called upstairs, “Get up, get dressed, and get ready for school!” It was a familiar routine and especially important when the school was administering standardized tests.

“I feel sick,” said the voice from the bedroom.

“You are not sick. Get up and get ready,” the woman replied, walking up the stairs and hovering outside the bedroom door.

“I hate school and I’m not going,” said the voice from the other side of the door. “I’m always getting things wrong, making mistakes, and getting told off. The teachers hate me and constantly complain about me. Nobody likes me, not even the school janitor.”

“I’m sorry, but you are going to school. We all make mistakes, so try not to take criticism so personally. Besides, I cannot believe that nobody likes you – you probably have lots of friends at school,” she continued. “Anyway, you have to go, you’re the principal.”

In all the years I attended school I never once considered that maybe the principal hated being there as much as I did. But from the time I was a small child all the way through my teenage years I absolutely despised going to school. I never would have guessed that one day I’d be “going to school” by choice, but here I am showing up to work each day – mostly happy to be here.

(I remember when I accompanied my oldest son to his first day at school some thirty-three years ago. As we entered the school he was excitedly jumping up and down in anticipation. I looked at him and sadly thought, “You poor boy; you have no idea that you are about to begin a 15-year sentence.”)

The essence of leadership is the assumption of ultimate responsibility. Occasionally, we may very well be that principal who is reluctant to get out of bed or a parent who is happy for someone else to watch their kids, but at the end of the day we assume the mantle because it is our job. True leadership is having the perspective that no matter the situation – or how it came to be – we must address and resolve issues to the best of our ability and for the betterment of those under our care.

Around the turn of the 20th century, as African colonialism began to wane and the continent slowly emerged as a potential economic market, two salesmen were sent by a British shoe manufacturer to different parts of the African continent to investigate and report back on market potential. After a few months the president of the company requested a progress report.

The first salesman reported, “Bring me home. There is no potential here – nobody wears shoes.” The second salesman reported, “Send large stock of various shoes. There is massive potential here – nobody wears shoes.”

In essence, what really differentiated the two salesman was that the first one only saw the situation as it was, and he therefore became locked into that paradigm and saw no way out. The second salesman had a vision of what the situation could become – and was willing to take responsibility to see it through.

This week’s Torah reading imparts wisdom that is relevant to this lesson.

“And God shall make you the head and not the tail; and you shall be above only, and you shall not be beneath [...]” (Deuteronomy 28:13).

This week's Torah portion discusses the amazing rewards for following the Torah path and the terrible punishments, God forbid, for veering from it. One of the rewards for fulfilling the Torah and mitzvot (commandments) is a promise that God will ensure the Jewish nation will become “the head and not the tail” – i.e. leaders and not followers.

One of the great medieval Biblical commentators was the Spanish sage known as Ramban (the Hebrew acronym for Rabbi Moses son of Nachman). Born in Girona, Catalonia around 1190 he was recognized as a prodigy from a young age. He was appointed rabbi of Girona as a young man and eventually he was selected as the Chief Rabbi of Catalonia. His written commentaries on the Torah and Talmud and works on philosophy are legendary. It would be hard to overstate his impact on Jewish scholarship. He died in the Land of Israel around 1270.

On the verse quoted above, Ramban is bothered by the seemingly unnecessary words “and not the tail.” Since the Jewish people are promised that if they follow the Torah and its commandments, they will become the “head” it would seem obvious that they would not be the tail. Why then, asks Ramban, is it necessary for the verse to explicitly exclude being the tail?

He answers that often a head is also a tail. How so? Consider a large company with many employees; obviously, the CEO cannot manage hundreds of subordinates. So, a system of management is put into place with staff employees, middle managers, and executive managers. The middle managers are thus leaders to some and subordinates to others.

Similarly, a nation can be ranked as a world power, making them a “head” over other nations; throughout history various nations ranked at the “top” – the Babylonians, the Assyrians, the Greeks, the Romans, etc. But as there are many nations in the world, most nations are in the middle and are therefore similar to middle managers; a “head” to some nations and a “tail” to others, with nations ranked both above and below them.

Ramban goes on to explain that in this verse the Almighty is promising us that if we follow the Torah we will be “ranked” at the absolute top – only a head and not a tail to any other nation in the world.

I once heard a brilliant class from my father on the subject of leadership, and utilizing Ramban’s insight he remarked that often leaders too are both the head and the tail. How so?

A proper leader is one who has a vision for his convictions and implements it. In other words, he sees the proper path, even if it is unpopular, and courageously guides his followers down that path. That is a true leader – one at the head of his constituency.

Unfortunately, most of the leaders of our generation are of another type – they are a head in title only, and a tail in practice. These leaders don’t have a conviction of their vision; they merely observe the prevailing sentiment of popular opinion and draw their agenda based on their constituency’s clamoring.

Sadly, in this situation, a head is really just a tail because this sort of leadership isn’t driven by vision or the betterment of his people, he is driven instead by “the tail” – those who he is meant to be leading. Unfortunately, when a leader abandons his vision to the whims of his constituents, his agenda always suffers because it invariably ends up following the lowest common denominator: i.e. “On what can we all agree?” (Or, what is currently trending on social media.)

Of the last ten U.S. presidencies only two or three have really tried to lead with a vision without wholly pandering to the baser desires of the foolish American people (Hey! Let’s try socialism!). This is how we have gotten to where we are today: An out-of-control deficit, looming disasters in Social Security benefits and other government safety nets, and a system of higher education that instead of preparing students for the real world, fills their head with the stupidest ideologies and bankrupt moral values.

Little wonder then that there is an overall disgust with the two prevailing political parties (almost half the country affiliates with neither party). This is what happens when the nation’s agenda is driven by the lowest common denominator instead of being motivated by a true leader. Truth and morality always suffer in these situations because the national agenda is motivated by popular demand and not by asking “What is the right thing to do? What will create the best future for our people?”

Unfortunately, this is the essence of our current predicament. Political intractability obscures the reality of our plight because no one will stand up and state the truth. Whether it is debunking the validity of the most ridiculous claims, condemning violent acts done in the name of a religion or ideological movements, or calling out the segment of society that continually lays the blame of its ills at the feet of others without taking real responsibility, most leaders today steadfastly refuse to call out the lies within the narratives of their constituents. They will not take a stand deemed to be unpopular because they fear losing their leadership position and “power.”

The Torah is teaching us how to change that. If we follow the commandment, we will be true leaders: We will have a real moral compass and a healthy vision for ourselves and the world. This is the path to being the head and not a tail; we filter out the nonsense, we do not follow the crowd, we lead mitzvah filled lives, and we become shining examples for the world to follow.

Torah Portion of the week

Ki Tavo, Deuteronomy 26:1 - 29:8

This week's portion includes: Bringing to the Temple as an offering the first fruits of the seven species special to the Land of Israel, declaration of tithes, the Almighty designating the Jewish people as His treasured people (Deuteronomy 26:16 - 19), the command to set up in the Jordan River and then on Mount Eival large stones that had the Torah written upon them in 70 languages, the command to have a public ratification of the acceptance of the law from Mount Gerizim and Mount Eival; the Torah then sets forth the blessings for following the law and the curses for not following it, and concludes with Moses’ final discourse. Verse 28:46 tells us the importance of serving the Almighty with “joy and a good heart.” The last verse of the portion instructs us, “You shall fulfill the words of this covenant and do them so that you will succeed in all that you do!”

Quote of the Week

It is a terrible thing to look over your shoulder when you are trying to lead – and find no one there.
- Franklin D. Roosevelt

Dedicated in Deep Appreciation to

Jeremy Goldstein

Thank You for Your Continuous Support

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