Rabbeinu Reb Yaakov Shimshon zt"l was of the greatest among the talmidim of HaRav HaKodosh Rabbi Pinchos of Koritz zt"l and remained close to him in spirit even when physical distance separated them.
The sefer Nesiv Mitzvosecha (Nesiv Hayichud, shvil 4, No 4) relates that Reb Yaakov Shimshon had a dream one night in which he saw the Shechinah crying and weeping in the image of a woman crying over the loss of her husband.
Upon awakening, Rabbeinu announced: "Rabbeinu hagodol, the great Reb Pinchos of Koritz, has passed away in Russia," and then, crying bitterly, he tore keriah as a talmid does for his Rebbe and mourned his profound loss.
Sure enough, a few days later the arriving news confirmed: Rabbi Pinchos of Koritz had returned his soul to Shomayim exactly at the time that his talmid muvhak Reb Yaakov Shimshon had seen his dream.
Rabbeinu served as rov and mentor to the community of Slavita and subsequently in Uman. From there he went on to become rov in Shepetovka where, despite his humility and even self- deprecation, he remained a zealot for Hashem, battling boldly against the porkei ol who wished to undermine Torah and those who adhere to its mitzvos.
Due to the magnitude of his power in chiddush and pilpul, he had a constant stream of talmidei chachomim of every sector of Jews coming to speak with him in learning. He would exhort them to rise in madreigoh through their learning and rectify their misdeeds.
Citing the following posuk, he explained: "Ushmartem va'asisem, you shall keep and guard the mitzvos for that is your wisdom and understanding in the eyes of all the people." (Voeschanon 4:6). Rashi explains the first two words to mean: you shall learn (Torah) and you shall do. Expounded Rabbi Shimshon, "Hakodosh Boruch Hu chose us above all the nations to be His people, giving the Torah to us and not to them because Yisroel learn in order to fulfill the Torah unlike the umos haolam for whom wisdom is an end in itself. In the eyes of the nations we are wiser and have a better understanding because our learning is al menas la'asos. It is therefore incumbent upon us to actually do this and to become better people as a result of our limud Torah."
Rabbeinu's heart burned with a strong yearning for Eretz Yisroel. It is said in his name that whoever buys a plot of land in Eretz Yisroel will never have it taken away, even when Moshiach comes. He spent endless time and energy towards the realization of his dream until finally in the year 5554 (1794) he was able to leave the Diaspora and travel up to the holy land to live.
Once, on a previous occasion, he managed to go to Eretz Yisroel for a visit that was planned to last for two months. His family far away in Europe waited for the time to be up, and then waited some more. Weeks passed and still there was no sign of Reb Yaakov Shimshon's return. Worried for his health and well-being, they had no way to contact him.
It was only after several anxiety-filled months that Rabbeinu finally returned home. His explanation for the delay was straightforward. "After two months in Eretz Yisroel I prepared, albeit reluctantly, to leave for home. As I was about to board the ship I passed a mirror and noticed that my face looked pale and wan. Afraid that the people here would speak badly about the Eretz Hakodesh, saying that there one becomes weak, I prolonged my stay, making sure to eat and drink plenty until I looked fit and healthy, and only then did I begin my journey home."
The sefer Divrei Torah of the Minchas Elozor of Munkacz brings a story that Reb Shimshon himself related.
"Before I went up to Eretz Hakodesh I turned to the yetzer hora, `Since I'm poor and destitute I don't have the money to pay the fares to Eretz Yisroel for both of us. I suggest therefore, that you take your choice; either you go and leave me here without you, or you stay here and allow me to live in Eretz Yisroel without your presence, free to serve Hashem as I wish.'
"My wily friend chose to remain in chutz la'aretz and allowed me to travel on my own.
"Naturally, I was delighted, but my joy was short-lived. No sooner had I disembarked from the ship and there he was — the yetzer hora coming towards me.
"`Didn't we agree that I would travel and you would stay there?' I demanded.
"He danced in front of me mockingly. `That deal you closed in chutz la'aretz was with one of my agents. Here in Eretz Yisroel, the holy land, I work in person to entice people to do aveiros.' "
"Listen to the awesome greatness of Reb Yaakov Shamshon of Shepetovka," retold the Rebbe Reb Bunim of Pershischa as his chassidim gathered closer to hear.
"During Rabbeinu's long-awaited journey to the Holy Land the ship was delayed considerably due to bad weather conditions.
"The night of Rosh Hashanah found them on the high stormy seas instead of spending the exalted Yomim Noraim in a shul in Eretz Yisroel as planned. As the night wore on the storm worsened. Swaying dangerously, the ship tried to hold its own against raging waves that grew increasingly higher and stronger, threatening to engulf the entire vessel.
"Standing on the ship's slippery deck, Rabbeinu held the railing tightly, his eyes scanning the horizon. Desperate eyes, waiting for the slightest sign of daylight, for the tiniest ray to herald the dawn. As soon as the darkness began to shed its cloak, making way for Rosh Hashanah morning, Reb Yaakov Shimshon knew the moment he had been anticipating had come.
"Swiftly, he raised a shofar to his lips and blew all the one hundred blasts in quick succession.
"As if in answer to his call the storm abated, the angry sea calmed down and the ship sailed on gracefully without further mishap."
Pausing, the Rebbe Reb Bunim looked around at the faces of his chassidim.
"I know what you're thinking. Just like everyone thought. They all thought that Rabbeinu wanted to blow the shofar so urgently, so that the zchus of the mitzva would protect him and his fellow passengers. But you're all wrong. Reb Yaakov Shimshon saw that the ship was about to sink. At any moment it could capsize choliloh, bringing their lives to a watery end. With what he thought were his final minutes, he wanted to be able to at least fulfill one more mitzva. Just another precious mitzva before he would leave this world!"
After reaching the shores of Eretz Yisroel, Rabbeinu settled in Tiveria, but not before he had visited all the kivrei tzadikim in the area.
A witness recounted that when he prayed at the grave of the tanna Rabbi Akiva, he repeated all the sayings of Rabbi Akiva from Shas Bavli and Yerushalmi by heart.
Once, a Yid in Tiveria fell out with his Arab neighbors. The latter summoned him to court for an almost certain death sentence. The distraught defendant poured out his troubles before the new rov who had arrived from Shepetovka.
Rabbeinu instructed him to give a pidyon nefesh to tzedokoh which the man gladly did, seeing it as his only hope of salvation.
On the appointed day, the trembling Yid made his way to the courtroom which was situated right on the banks of the Kinneret, bordering Tiveria.
As he was approaching, he beheld his Arab neighbor accompanied by his lawyer ascending the steps to the courthouse, causing him to quake inwardly.
All at once, there was a loud rumbling sound, followed by panicky screams and a loud splash! The Yid rubbed his eyes in disbelief. Where a broad staircase had stood a moment earlier there was now a mere pile of rubble. The structure had collapsed, throwing the two accusers into the sea together with all their incriminating documents.
When the grateful man came to thank Rabbeinu and recount the nes, the latter's reaction was not one of surprise.
"It's not a mofes at all; it's an open posuk in the Torah, "Poso'ach tiftach es yodecho."
The intonation on the first two words are `dargo tevir' (literally `broken steps'). So there you are. By opening your hand and giving tzedokoh, you merited that the steps should break, thereby saving your life."
On the 3rd of Sivan 5561 (1801) Rabbeinu was niftar. He lies buried in the old cemetery in Tiveria close to the tziun of HaRav Nachman of Horodenka zt"l.
There are no lofty inscriptions on his small headstone, only: "The Rav muvhak, the Chossid, holy one of Hashem."