“Avraham passed away and died at a good age, elderly and full of days and he was gathered to his people.” (Bereshith 25:8)
The day that Avraham our father departed from the world, the great men of the nations stood in line and said: Woe to a world that has lost its leader, and woe to a ship that has lost its captain. (Baba Batra 91a)
What is the difference between a leader and a captain to which this Midrash seems to elude? Are they not the same? And if so, why did the Midrash state both? If one is the mashal, the parable, and the other the moral, the Midrash should have first mentioned the captain (parable) and consequently the leader, the moral. We must therefore conclude that the Midrash tries to hint at a profound difference between both these tasks which throws light on the personality of Avraham.
There are two distinctive differences between a leader and a captain. A leader always walks in front of his followers; he is the first, while a captain is the last to leave the ship. Secondly a leader has a personal interest in his destination, while a captain does not.
A leader is not only a leader by virtue of his followers but also because he is part of the group he leads. Their destination is also his. He needs to get there as much as they do. As such he does not behave out of character. He himself benefits from leading the others. His self actualization comes about through emotionally participating in the actual journey.
This however is not true for the captain, who has no personal interest in his destination. His task is to bring his passengers to their destination, and in all likelihood will immediately turn around and head back from whence he came. He has no part in the group’s desire to reach a specific objective. He only travels with them for their sake.
Leadership and walking in front often entail a neglect of those who were are left behind. The general is unable to turn around to take care of his last soldier at the back of the battalion. His mind is on his destination and his mission is accomplished when he reaches it. That some people pay the price for getting there is not his concern.
The captain’s concern is a totally different one. He wants to take care of all his passengers and will ensure the safety of the very last passenger before abandoning the sinking ship.
It is a combination of these two qualities which we find in Avraham’s personality. As a spiritual leader who started a revolution which turned the world around, he initiated a movement which until this day has had an unprecedented effect on mankind’s attitudes and behavior. His devotion to monotheism and ethics is legendary. As such he was an unparalleled leader and walked in front of everybody else. But he was also a captain who cared for the underdog and who pleaded with God not to leave the wicked people of Sedom and Amora behind. While his eyes were focused forward, his heart was alert to what happened behind him.
Simultaneously he was a leader who shared in some of the goals of his generation and showed them the way in their own personal lives. Above all, however, he was the man who traveled with his passengers, often getting involved in issues in which he was not instrumental and had no wish to be. On such occasions he was as selfless as a captain.
To be a Jewish leader is to be a captain as well.
 See also Rabbi Avraham Yitzchak Kook, Midbar Shur, Chayei Sara.
This essay is from my new book, Cardozo on the Parashah: Bereshit | Genesis, (Kasva Press, 2019)
The book is available at Amazon and other online booksellers. In Israel, the book can be found and Pomeranz Booksellers in Jerusalem.
As taken from, https://www.cardozoacademy.org/thoughts-to-ponder/chaye-sarah-leader-or-captain/?utm_source=Subscribers&utm_campaign=362c5a9cbc-RSS_EMAIL_CAMPAIGN&utm_medium=email&utm_term=0_dd05790c6d-362c5a9cbc-242341409