1) THE STORY OF ILFA AND REBBI YOCHANAN
QUESTIONS: The Gemara relates the story of Ilfa and Rebbi Yochanan. Ilfa and Rebbi Yochanan suffered from abject poverty while they immersed themselves in Torah learning. Their situation became so difficult that they decided to leave the Beis Midrash and go to work in fulfillment of the verse, "There will be no destitute among you" (Devarim 15:4). When they were on their way to find work, Rebbi Yochanan overheard two Mal'achei ha'Shares conversing with each other. The Mal'achim said that these two people deserved to be killed for leaving the life of eternity (Torah study) and involving themselves in the temporary life of pursuing a material livelihood. The Mal'achim added that the only reason they did not kill Ilfa and Rebbi Yochanan is because the fate of one of them would soon take a propitious turn. Rebbi Yochanan heard this conversation and decided to continue learning Torah in poverty and not to go to work. Ilfa, who did not hear the words of the Mal'achim, went to work.
By the time Ilfa returned from his business endeavors, Rebbi Yochanan had been inaugurated as the Rosh Yeshiva, a position of great prestige and wealth (Rashi). The people of the town said to Ilfa upon his return, "Had you stayed and learned Torah [like Rebbi Yochanan], you would have become the Rosh Yeshiva!"
When Ilfa heard this, he ascended the mast of a ship and suspended himself in the crow's nest at the top. He proclaimed, "If anyone can ask me a question which I cannot answer about the source in the Mishnah of any statement of Rebbi Chiya and Rebbi Oshiya in the Beraisa, I will jump down from here and drown myself!"
This incident poses a number of questions.
Why did Ilfa climb to the top of a ship to make his announcement? Why did he not simply go to the top of a Beis Midrash or some other structure on land?
Why did Ilfa threaten to kill himself? The Torah forbids one from killing himself, regardless of the amount of distress he experiences. (See BEN YEHOYADA.)
ANSWER: RAV JOSEPH PEARLMAN shlit'a of London quotes his father, RAV REFOEL DOVID zt'l, who gave a beautiful explanation for this Gemara (as cited in HA'MEIR, Parshas Vayechi 5742).
Rav Refoel Dovid explained that when Ilfa returned from his business endeavors, he felt that he was being criticized for not having attained the heights in Torah which he could have attained. He felt that this criticism was unjust. He maintained that his choice to follow the path of "Torah Im Derech Eretz," learning Torah while working for a livelihood, was justified. He wanted to prove to his detractors that his Torah learning had not suffered at all as a result of his involvement in pursuing a livelihood (as Rashi writes, "[Ilfa said:] Even though I became involved in commerce, I did not forget any of my learning").
Ilfa was a merchant who, like the people of Zevulun, traveled by ship to faraway places to trade his wares. (This might be why he was called Ilfa; the word "Ilfa" in Aramaic means "ship.") By climbing to the top of the mast of the ship, Ilfa demonstrated that although he had reached the pinnacle of success in his business, his involvement in business had not interfered with his Torah learning.
He declared that he was prepared to answer any question in Torah that would be posed to him, and if he would be unable to answer it he would "jump down" from the top of the ship -- that is, he would leave his immensely successful business and wealth and abandon his Derech of learning and working together -- and "drown himself" completely in the sea of Torah, as Rebbi Yochanan had done. If his Torah learning had suffered as a result of his involvement in business, he was willing to jump down from the world of business success and immerse himself in the sea of Torah.
According to this explanation, Ilfa felt no regret for the path he had chosen. He considered himself to have chosen the correct way in the service of Hash-m, just as Rebbi Yochanan felt that he had chosen the correct way in the service of Hash-m. How, though, could Ilfa's path have been an acceptable one, if the Mal'achim themselves said that one who leaves Torah learning deserves to die?
RAV REUVEN MARGOLIYOS (introduction to Margoliyos ha'Yam) suggests that both Ilfa and Rebbi Yochanan did exactly what they were supposed to do; Ilfa accomplished no less than Rebbi Yochanan. The Midrash (Shir ha'Shirim Rabah 8:7) says that Rebbi Yochanan told Rebbi Chiya bar Aba that he once owned a vast amount of real estate, but he sold it in order to continue learning Torah. Rebbi Chiya bar Aba cried for him that he no longer had anything with which to support himself when he would become old. Ilfa, on the other hand, may have come from a very poor family. Had he not worked for a living, he would have had nothing at all to eat. Since Rebbi Yochanan had what to eat and only wanted to work as much as necessary to ensure that he would have sustenance in his old age, he made the right choice when he decided to abandon his plan to work and instead to live off of his inheritance until it would be depleted. He would trust in Hash-m and not worry about what he would do for sustenance in his old age. Ilfa, in contrast, had nothing to sell and nothing with which to support himself, and thus he made the correct choice when he decided to involve himself in business.
]Why, though, did the Mal'achim want to kill both Ilfa and Rebbi Yochanan for leaving the life of Torah study, if Ilfa's choice was justified?
Moreover, the Gemara explains that Ilfa and Rebbi Yochanan were sitting below a weak wall which the Mal'achim wanted to topple on them. What is the significance of the fact that the wall was weak? If one who leaves Torah learning indeed deserves death, then the Mal'achim would have had grounds to collapse the wall onto Ilfa and Rebbi Yochanan even if it would have been a strong wall.
The Gemara earlier (20a) says that one may not walk below a weak wall because he thereby diminishes his merits, which become "used up" by protecting him from the danger that the weak wall poses (Berachos 55a, Rosh Hashanah 16b). Ilfa and Rebbi Yochanan's lives were in danger simply because they negligently sat under a weak wall. The Mal'achim said that had they still been involved in learning Torah, their Torah study would have protected them (as the Gemara says in Sotah 21a). Since Torah is not within the realm of nature, those who study it are freed from nature's grasp (as the Midrash says in Bamidbar Rabah 10:8: "The only one who is truly free is one who toils in Torah"). Once they decided to stop learning Torah and become involved in a worldly occupation, they no longer merited Divine protection from natural calamities. Nevertheless, they were protected by the merit of Rebbi Yochanan who was destined to become the generation's next Torah leader.

OTHER D.A.F. RESOURCES
ON THIS DAF