This past summer, artificial intelligence succeeded in producing a song called Heart on My Sleeve which was an artificial musical collaboration between Drake and the Weekend, while I am not a devoted fan of either, people in the know were convinced of its authenticity. I saw one reporter was able to fool her bank by reproducing her voice through AI. A local rabbi told me that they used a chatbot to give a D’var Torah at a board meeting, with strong reviews. So, in a moment of writer’s block before Rosh Hashanah, I turned to Chat GPT and prompted the computer to “write me a sermon in the style of Rabbi Andrew Rosenblatt.” On the one hand I was relieved, because I was disappointed with the product — my job is safe… for now. On the other hand, this is what the chatbot produced.
L’shanah tovah, my beloved congregation!
As we gather here today, on this sacred day of Rosh Hashanah, the Jewish New Year, I am filled with a profound sense of gratitude and awe. It is a privilege to stand before you once again, to usher in this new year with hope, reflection, and renewed commitment to our faith. And so, I want to speak to you today in the style of our dear Rabbi Andrew Rosenblatt, may his memory be a blessing, who inspired us with his wisdom and compassion.
I must say it was a bit of a shock to hear of myself in the blessed memory category – בלי עין הרע. My first reaction was to analyze why this is so. Is it because my name is Andrew – as opposed to something more Hebrew/Biblical sounding – that it used the style of a Reform rabbi? Was its inability to copy my style a function of how little published material of mine it found on the web?
I had to remind myself, it is a soulless entity that is trying to approximate humanity by thinking what is the next most probable statement to come out of my mouth. I am glad that I still have enough connection to my own soul to be able to be more skilled than the computer. More and more of our communication is touch-less, and without human involvement. I can assure you that you are receiving birthday cards, emails, apology letters that have been written by a computer.
Even Hashem is getting automated prayers. Canadian Pulitzer Prize-nominated novelist Nathan Englander wrote a book called Kaddish.com. The protagonist, Larry, has just lost his devout father. His sister, together with her rabbi and the head of the chevra kadisha, try to browbeat him into saying Kaddish. They settle on a compromise; he will find a representative. After a quick search Larry finds the website kaddish.com, which connects him to a yeshiva that will help one find a candidate or two to recite the Kaddish on their behalf for a loved one. Larry calls it “JDate for the dead.”
While in 1999 this was in the imagination of Nathan Englander, in 2023 such a website actually exists, with exactly that name. It made my heart sink. It costs $75 for one Yahrzeit, $150 for Yahrzeit in perpetuity, $175 for daily kaddish for 11 months, and for $250 kaddish will be said 3 times daily for 11 months and for Yahrzeits in perpetuity. It is about as soulless as one could possibly imagine.
Larry the protagonist says one line that I found very striking. “Does anyone really think G-d sits up there with a scorecard checking off every one of Larry’s blessings?” This is interesting, because I often think we do think exactly that. We see blessing as a transaction. My father paid for me to get into medical school; I will pay for me getting into heaven. How do we pay for heaven? Is it with prayers?
It is hard to deny transactional Judaism. There are many rituals and metaphors that lead us in that direction. We think of our sins and mitzvot sitting on a scale, being judged for the new year. It is as if putting on Tefillin often enough makes up for slanderously gossiping, or as if giving a big donation makes up for infidelity.
I remember in university I had a friend in a very competitive engineering program. He would attend morning services whenever he had a midterm or a final. It was a very transactional approach. Here I am Gd, maybe you could award me with an extra 10 points or so for the Aliya of my GPA.
This transactional mentality is very old, it is even at the heart of the Haftorah that we read just minutes ago. The people cry out to Gd and they say,
לָמָּה צַּמְנוּ וְלֹא רָאִיתָ עִנִּינוּ נַפְשֵׁנוּ וְלֹא תֵדָע הֵן בְּיוֹם צֹמְכֶם תִּמְצְאוּ חֵפֶץ וְכָל עַצְּבֵיכֶם תִּנְגֹּשׂוּ.
Hashem answers them plainly, On the fast day you came with your shopping list of personal needs. Isaiah says to them, “you fast with grievance and strife…” Really, they fast with an edge, with anger at Gd, maybe. Gd says, “do you call this a fast and a day of favour to Hashem?” Isaiah then repaints the picture like this.
No, this is the fast I desire:
To unlock fetters of wickedness,
And dissolve the groups that pervert justice,
To let the oppressed go free;
To annul all the unfair contracts
It is to share your bread with the hungry,
And to take the wretched poor into your home;
When you see the naked, to clothe them,
And not to ignore your own kin.
Essentially, Gd is saying that this is not pinball; you don’t score points every time you say Shema.
Rabbis for the past thousand years have been wrestling with this problem. Rambam laments the fact that we reward children with candy to encourage the study Torah. He says they soon outgrow candy and they want bigger rewards, like clothing. I had no idea, Cairo where Rambam lived was such a fashion hub in the 12th century! When they mature further the children want money. At some point money is no longer a good enough reward, so you have to reward them with honour and ego boosters to inspire Torah study. Rambam laments that when you start with the reward game, it is hard to rediscover the intrinsic rewards. Alas, even Rambam is resigned to the transactional; “and all of this is despicable, nonetheless, it is necessary because of the smallness of the human intellect that he make the objective of wisdom something else besides wisdom.”
Rabbi Yitzhak Hunter takes on the Talmudic metaphor of the scales. If you are righteous, your mitzvot outweigh your sins, and Hashem immediately judges you for good. If you are wicked, Gd judges you immediately for bad. Most of us are in the middle at 50/50. It would seem that we must perform more mitzvot to tip the scales. Rabbi Hunter is shocked at this. How do you reconcile your accounts if you have no idea what each mitzvah is worth, and what the debit is for each sin? He concludes that being in the middle realm means that you have to reshape your character. It is not about scoring more points; it’s about being a better all-around player.
There is a secret that you should know about Kaddish: its origin. The early sources on Kaddish are all about leading the prayers. The earliest source does not actually have the mourner saying Kaddish, but rather leading the full prayer service. However, the skills to learn to lead the prayers are many. Shacharit, the morning service, is 70 pages. Kaddish is 1 page. There are so many Kaddishin in a service because each of the mourners can then have a turn in leading. In short, now that father or mother has passed away, the matriarch, the patriarch is gone, this puts the child in their wake in a place to be the leader.
Maybe one of the best expressions of this idea came from the most famous Jew from my hometown, Henrietta Szold. Her friend Hayim Peretz offered to say Kaddish for her mother. Szold’s letter to him is timeless.
It is impossible for me to find words in which to tell you how deeply I was touched by your offer to act as “Kaddish” for my dear mother. I cannot even thank you — it is something that goes beyond thanks. It is beautiful, what you have offered to do — I shall never forget it.
You will wonder, then, that I cannot accept your offer. Perhaps it would be best for me not to try to explain to you in writing, but to wait until I see you to tell you why it is so. I know well, and appreciate what you say about the Jewish custom; and Jewish custom is very dear and sacred to me. And yet I cannot ask you to say Kaddish after my mother. The Kaddish means to me that the survivor publicly and markedly manifests his wish and intention to assume the relation to the Jewish community which his parent had, and that so the chain of tradition remains unbroken from generation to generation, each adding its own link. You can do that for the generations of your family, I must do that for the generations of my family.
Kaddish is not a transaction. It is not about points on a scorecard as Larry quipped about kaddish.com. It is not a token; it is not Mitzvah pinball. Kaddish and Yizkor are publicly and markedly manifesting one’s wish and intention to assume the relation to the Jewish community which the parent had.
Henrietta Szold, the founder of Hadassah Women, wrote that letter in 1916. However, her exact turn of phrase hits harder in 2023 than it did in 1916.
Assume that one’s relationship to the community is the exact opposite of what Henrietta Szold wrote. This would be synonymous with the more recently-coined term capable loner. The concept of the capable loner was developed by columnist and political analyst Yuval Levin. Levin argues that the technological advances of the pandemic are making us all more capable loners. The massive technological adoptions of the pandemic,
… means that we are using this time to hone our capacity for isolation and solitude. “Social distancing,” “remote work,” and “distance learning” are the watchwords of this national response … so that the habits we are building will enable us to more effectively stand apart when this is over… Rather than a sense of mutual dependence, then, we might walk away from this crisis as even more capable loners… A great deal of what we have thought of as the information revolution in the last two decades has amounted to novel ways of avoiding real social interaction.
One can pick up Starbucks coffee with remote ordering without saying a word to anyone. How often have you texted someone because you lacked the emotional energy to actually talk to them? Sadly, there is also kaddish.com, where one can have kaddish said without any relationship to any community.
The cost of a transaction used to be higher: a conversation with the Barista, maybe even getting them to pronounce your name correctly, looking someone in the eye when you talk. Now we have reduced the transaction to the funds transferred.
There is a story in the bible of miracles-for-cash. It is about a Syrian general named Na’aman. He is stricken with leprosy – Tza’arat – and the young Israelite girl that he took captive suggested that he go to the prophet Elisha to cure him. He heeds her advice and travels to the prophet – who instructs him to bathe seven times in the Jordan River and emerge with the skin of a six-year-old. Na’aman, the powerful general, attempts to give Elisha a gift, — Elisha refuses. Na’aman entreats further. Elisha refuses. Na’aman then takes an oath saying that he will never engage in the worship of any other Gd but Hashem. The general of the Syrian court pledged himself to Hashem and Torah. Elisha knew that he could not let Na’aman pay for his miracle. He could not let him off with a price so cheap. By refusing the transaction Na’aman had to deal with the enormity of Gd.
But defeat is snatched from the jaws of victory. As Na’aman returns to Syria, one of the students in the prophetic academy Gechazi runs toward him and says, “my master, my teacher let you get away before accepting your gift.” Then Naaman gives him a little silver and several pairs of clothing. The Syrians returned to being the enemies of Israel. Na’aman had traded epiphany for a little silver and some clothing.
Who are we in that story? Are we Elisha or Gechazi? Imagine the Kaddish said by each of these men. Elisha is like Henrietta Szold, wondering how he can fill the place of his parent, how he can add to the community, how he can make a spiritual commitment, how he can attach himself to the community, to the mission. There is an insurmountable mountain of gratitude. The only thing that can answer for the gifts of upbringing by parent and community is commitment of the entirety of one’s character. That is what you owe, “to assume the relation to the Jewish community which his parent had, and that so the chain of tradition remains unbroken from generation to generation, each adding its own link.”
I always end Yizkor by speaking to those who are about to observe Yizkor. I want to speak to all of the rest of you first. I have spent the last 25 minutes rejecting the concept that Kaddish is a transaction with Gd. I have tried to demonstrate that it is a call to leadership, a call to embody the values that your family has carried for the past 100, 300, 1000 years — the values dictated by the Torah. The worst time to learn what that means is when the actual mourning begins and you are called to it. Your leadership has to start now. Learn that leadership when your parents can take that pride in seeing you there.
To those observing Yizkor, you know that what you owe to those who built this shul, is not the small token that is pledged in the text of the Siddur. It has to be bigger than that. Our culture is in a crisis of disintegrating into capable loners. We need your leadership. We need your presence. We need to rebuild the week in and week out vitality of this community — that is what we owe to those who built this community. We owe them the effort that maintains the vitality they worked so hard to build.
Rabbi Rosenblatt

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