The Death of Moshe: The Punishment for a Reluctance to Lead

The holiday of Simchat Torah has become one of the more joyous holidays on the Jewish calendar. Dancing around the bima, and in some places in the streets, with the Torah marks the conclusion of the annual Torah reading cycle and the beginning of the next year's cycle. However, along with the joy and happiness of completing the Torah comes the death of Moshe Rabbeinu.
The emotional ending of the Torah is made even more dramatic by the words of Rabbi Shimon in the Gemara (Bava Batra 15a), speaking of the last eight pesukim of the Torah, which take place after we are informed of the death of Moshe:

עד כאן הקב"ה אומר ומשה אומר וכותב, מכאן ואילך הקב"ה אומר ומשה כותב בדמע
Until here God spoke and Moshe repeated and wrote (the Torah), from here and on God spoke and Moshe wrote with tears.

The Maharsha (Chidushei Aggadot Bava Batra 15a) writes that Moshe actually used his tears to write the last pesukim of the Torah instead of the ink he used for the rest of the Torah.
Why did the Torah need to end on such a sad note, with the death of the greatest teacher and prophet ever to live, before he could enter the land he so desired to dwell in?
The simple explanation is that Moshe was punished for his part in the sin of the rock (Bamidbar 20). However various Midrashim, most likely troubled by the severity of Moshe's punishment, sought alternative reasons for God denying him entry into the Land.
One such approach, which appears throughout many Midrashim, claims that Moshe was denied entry into the Land because of a sin that took place well before Bnei Yisrael entered the desert. The Mechilta of Rabbi Shimon bar Yochai (Parshat Va'era 6:2) relates in the name of Rabbi Tarfon:

אמר הקב"ה גלוי וידוע לפני שישראל ראויים לצאת ממצרים ולהנתן ביד עמון ומואב ועמלק אלא בשבועה נשבעתי ללחום מלחמתם ואושיע אתכם... והריני מבקש להוציאם ממצרים, ואתה אומר לי: שלח נא ביד תשלח

God said: It is known to Me that Bnei Yisrael is worthy to leave Egypt and then be given over in the hands of Amon, Moab and Amalek, but I have taken an oath to fight their wars and save them. And behold I am asking you to take them out of Egypt and you tell me: "Send whomever you shall send!?"

According to Rabbi Tarfon God became angry with Moshe because he had the audacity to tell Him to send someone else in his stead to lead the people out of Egypt. God had preordained a plan to redeem the people and had backed up His promise by taking an oath that He would fulfill His word and now Moshe decided that he did not want to be part of His plan; in the opinion of Rabbi Tarfon, Moshe's modesty, in this case, was misplaced.
The same Midrash quotes the opinion of Rabbi Nechemiah, who harshly criticizes Moshe's reluctance to lead.

גלוי וידוע לפני צער ישראל במצרים... צער קשה... הם שרויים בצרה ואתה שרוי בריוח ואני כבר פקדתי אותם ברחמים להוציאם ממצרים, ואתה אומר שלח נא ביד תשלח
It is known to me the pain of Israel in Egypt...the intense pain... they are in a state of pain and you are in a state of comfort and I have already remembered them with mercy to redeem them from Egypt and you say "Send whomever you shall send!?"

According to Rabbi Nechemia, God was outraged with Moshe for not identifying with the pain and suffering of his own people. Here he was sitting comfortably in Midian with his brethren suffering in the bitter slavery of Egypt. He was given the opportunity to save the people and he shrugged it off, claiming that someone else should do it.
According to both Rabbi Tarfon and Rabbi Nechemia God was angry with Moshe for not wanting to lead. With all of that said, they do not make a connection between God's anger and God's denying Moshe entry into the Land. Another tanna, Rabbi Elazar ben Arach, however, does make the connection.

ר' אלעזר בן ערך אומר: וכי מפני מה נגלה הקב"ה משמי מרום והיה מדבר עם משה בסנה, והלא היה לך מארזי הלבנון ומראשי ההרים ומראשי גבעות, אלא השפיל הקב"ה את שכינתו ועשה דברו כדרך ארץ, שלא יהיו אומות העולם אומרים מפני שהוא אלוה ובעל עולמו עשה דברו שלא כדין. לפיכך כבש הקב"ה את משה ששה ימים ובשביעי אמר לו שלח נא ביד תשלח
Rabbi Elazar ben Arach says: Why did God descend from the Heavens and speaking to Moshe from a bush? He should have spoken to him from the cedars of Lebanon, from the mountaintops or hilltops! Rather, God lowered His Presence and made His speech natural so that the other nations would not say that because he is God and Master of the world, he followed his word. Therefore God courted Moshe for six days and on the seventh day Moshe told him, "Send whomever you shall send."

According to Rabbi Elazar ben Arach, God brought Himself down to Moshe's level and even courted him for six days, but Moshe rejected God's recruitment pitch. Rabbi Elazar continues to illustrate his point through an analogy:

משלו משל למה הדבר דומה, למלך שהיה לו עבד והיה אוהבו אהבה גמורה. בקש המלך לעשותו אפטרופוס שלו להיות מפרנס בני פלטין של מלך. מה עשה המלך, תפס את העבד בידו והכניסו לבית גנזיו, והראהו כלי כסף וכלי זהב אבנים טובות ומרגליות וכל מה שיש לו בבית גנזיו. ומאחר כן הוציאו והראהו אילנות גנים ופרדסים... לאחר כן כבש העבד את ידו ואמר איני יכול לעשות אפטרופוס להיות מפרנס בני פלטין של מלך. אמר לו המלך: הואיל ולא היית יכול לעשות אפטרופוס, למה הטרחתני כל הטורח הזה, וכעס עליו המלך וגזר עליו שלא יכנס לפלטין שלו. כך כבש הקב"ה למשה ששה ימים ובשביעי אמר לו שלח נא ביד תשלח. נשבע לו הקב"ה שלא יכנס לארץ ישראל, שנאמר: לכן לא תביאו
To what can this be compared to? To a king who had a servant whom he truly loved. The king wished to appoint the servant as his caretaker to support the king's subjects. What did the king do? He took the servant by the hand and brought him into his treasure house and showed him his silver and gold utensils, his precious stones and pearls and all of the other contents of his treasure house. Afterward he took him out and showed him his trees, gardens and orchards. שׁAfterward the servant withdrew his hand and said, "I cannot be the caretaker of your subjects." The king said to him, "Since you had no intention of being a caretaker, why did you burden me to show you all of this?" The king became angry at him and decreed that he could not enter his palace. So too, God courted Moshe for six days and on the seventh day, Moshe said to him, "Send whomever you shall send." God swore to him that he would not enter the Land of Israel, as it says, "Therefore you will not bring them..."

Rabbi Elazar ben Arach explicitly writes that even before Moshe went to Egypt to take the Jewish people out of slavery it had been determined that he would not be able to enter the Land of Israel. His sin was unforgivable; he did not want to lead the people and in doing so he spurned God.
According to the tanaim in the Midrash, Moshe was punished because he was initially reluctant when asked to lead Bnei Yisrael out of the treacherous and inhumane conditions in Egypt. Moshe was fit to lead and initially refused to do so; even though he eventually relented, his inability to recognize his duty to the Jewish people was so severe that he was punished so harshly.