Rabbi Lawrence Kelemen often talks about the "Chain of Transmission" in Judaism, and how the existence of this chain bolsters the idea the mesorah is correct. Rabbi Kelemen has worked hard to trace back a mesorah going back rebbe-talmid from Moshe all the way to modern times. Rabbi Kelemen claims that this list is verified from four different sources and the existence of such an unbroken chain strongly bolsters the authenticity of the Torah narrative.
(Here is a link to the mesorah list: https://www.simpletoremember.com/articles/a/mesora/)
On the surface, this list seems impressive, and Rabbi Kelemen's point is definitely worth thinking about. The problem is that the closer one looks at the list, it becomes clear that aside from internal contradictions, in order to accept the truth of the list, one must also accept the following two premises:
The standard chronology accepted by all historians of the ancient near east is wrong by a whopping 165 years
All sorts of supernatural events can happen (people living for hundreds of years, people learning the entire Torah in one day, etc.) in order for the list to be historical.
The fact that one must first accept the supernatural claims of the Torah before the list makes sense makes Kellerman's point circular. His argument is essentally, first, believe in the authenticity of the Torah, and then I will prove to you the authenticity of the Torah.
So what are the issues in specific? Here are ten problems with the mesorah list:
ISSUE 1: Moses, Joshua, and Pinchas live too far apart
Right in the beginning, one hits a major snag. The first three people, Moses, Joshua, and Pinchas, are all contemporaries. The next person on the list, Eli, however, lived hundreds of years later.
Consider the following facts:
Eli was one of the last shoftim, taking over after Shimshon HaGibor, and Kellerman's chart records a 316 year period between Yeshua's death and Eli's death.
The pesukim record that Eli died at the age of 92 and only took over as shofet for 40 years.
That leaves a full 264 years (!) to be filled in between Yeshua's death and Eli's reign as shofet.
The only person to fill this spot is Pinchas - a man who was already old enough to command the Jewish forces during the attack of the Midianites in the desert (1310 be), making him many hundreds of years old by the time Eli is born.
Sure maybe it is true, Eli learned in the yeshiva of a 400-year-old man - but Kelemen's point is lost. Without allowing for a man to live 400 years in order to pass on the mesorah, there is a massive gap right at the beginning of the list.
ISSUE 2: The list says that Dovid received from the mesorah from Shemuel.
The problem is that the pseukim never mention that Shmuel was David's rebbe. In fact, many other people seem to have a mentorship position with Dovid (Achitofel, Uriah Hayiari, Nosson HaNavi, etc.), but not Shmuel. Shmeul died before David took over the kingship from Shaul, and during that period, David spent most of his time moving around, hiding from Shaul. This leaves precious little time for Dovid to learn the entire Torah from Shmuel.
To get around this issue, the Midrash Shmuel says that the night that Dovid ran away from Saul, Shmuel clandestinely met him taught for one night. During that nighttime meeting, Shmuel taught Dovid the entire Torah making him his talmid to pass on the mesorah.
Think about this for a moment.
According to this Midrash, our entire chain of Mesorah- containing all its millions of details - are linked to us based on a one-night conversation between Dovid and Shmuel. It seems to be a very low bar is being set for this "chain of transmission" to be established.
ISSUE 3: Dovid passing the mesorah to Achyah Hashiloni
The next person after Dovid, namely Achyah Hashiloni, is also a bit hard to swallow. According to the pesukim Achyah Hasiloni was a prophet who lived two generations later during the times of Yerevam. Chazal (Babba Basra 121b) also say that Achyah Hashiloni was alive during the exodus and was many hundreds of years old by the time he makes his first appearance in Tanach after the death of King Solomon.
It is very odd that Achyah Hashiloni is considered to have received the mesorah from Dovid given the fact that he was alive before Moshe was born and personally stood at Har Sinai. Again this is another indication that this entire list is not really authoritative.
ISSUE 4: Eliyahu receiving the mesorah from Achyah Hasiloni
The next person on the list - Eliyahu - is also problematic. According to Chazal, Eliyahu IS Pinchas - again, someone who personally stood at Har Sinai. You may believe that this Gemara is not literal, but almost all the Rishonim grapple with this issue. The overwhelming consensus of authorities is that this list can only exist according to the opinions that pinches and Eliyahu are separate people. While this may solve the problem, it still effectively weakens the power of this "chain of transmission." We no longer have any idea who these people are anymore.
ISSUE 5: Yehoyadah receiving the mesorah from Eliyahu
The next person on the list - Yehoyadah - is recorded as living 130 years. No big deal, although it does seem like he is a little larger than life. Another problem with Yehoyadah is that Chazal says that he was a Chohn Gedol - yet his name does not appear in the pesukim that lists all of the Cohanim Gedolim.
ISSUE 6: Zechariah receiving the mesorah from Yehoyadah
The next person - Zechariah - is deeply problematic. Firstly we have no idea who this Zechariah is. He can be one of two biblical characters, either Zechariah the son of Yehoyada, or he can be the great prophet, Zechariah. Neither of these options work.
Zechariah, the son - cannot work because the pesukim indicate he died at the same time as his father, making him incapable of passing on the torch between his father and anyone else. There are also several other dating issues with this suggestion.
Zechariah the prophet - this is the natural assumption when looking at the list, but this suggestion is impossible. Zechariah the prophet is recorded as being the rebbe of Baruch and Yirmeyah - people who lived several hundred years later.
ISSUE 7: The later prophets
So far, while requiring numerous fantastical life spans to fill in plot holes, the list does maintain a sense of inner coherence. Yet from here on down, the list rapidly devolves. Kellerman bases his list on the Rambam who list the next eight people in the chain as:
Hoshea (575 B.C.E.)
Amos (560 B.C.E.)
Isaiah (548 B.C.E.)
Micah (560 B.C.E.)
Yoel (510 B.C.E.)
Nachum (510 B.C.E.)
Chavakuk (510 B.C.E.)
Tzafaniah (460 B.C.E.)
The problem is that we have no record of these people learning from each other. The source of the Rambam is simply the fact that Chazal and the pesukim allow a more or less chronological sequence of when each prophet sermonized. Once the Rambam established the general chronology, he simply assumed - with absolutely no source that we know of - that each prophet received the mesorah from the previous prophet.
Again, just to be perfectly clear - it never says anywhere that these individuals had any connection with each other -certainly not as Rebbe and talmid of the entre mesorah. All it says is that these prophets preached to the Jewish people in a particular chronology. That's it. The Rambam is simply engaging in his imagination to assume that these people were passing on the torch of the mesorah to each other. This is analogous to saying that Bush taught the mesorah to Obama who taught the mesorah to Trump based on the fact that they were presidents in a particular sequence.
ISSUE 8: Yirmeyahu
The next person on the list -Yirmeyahu- is also problematic. According to the chart, he was the talmid of Tzafaniah. Yirmeyahu lived during the exile of the ten tribes, but according to Chazal Yirmeyahu was born during the time of Achav and Ezevel. The Midrash says that when Ezevel was killing out the prophets, Yirmeyahu's father impregnated his mother and then fled the kingdom. This Midrash would make Yirmeyahu a contemporary with Eliyahu Hanvai and well over 200 years old by time Tzafaniah was on the scene. This reality makes Yirmeyahu being receiving the mesorah from Tzafaniah deeply unlikely.
ISSUE 8: Ezra and the Persians
The next problem is Ezra and Shimon Hatzadik, but it could be anytime before that also.
These are the facts:
the bais Hamikdash was destroyed in the year 70 CE. this is attested to from multiple independent lines of evidence.
Jewish tradition says that the second temple stood for 420 years. That means that Ezra finished rebuilding the second temple during the year 350 BCE.
The truth is that the second temple was actually rebuilt 165 years earlier - during the year 515/516 BCE. Therefore if Ezra and Nichemia are historical characters - which presumably they are - then they lived in the year 515 BCE.
Shimon hatzadik, the next person on the list after Ezra is recorded by Chazal and Josephus as the high priest who met Alexander the great during the year 332 BCE. According to Chazal Shimon hatzadik was a cohen gadol and one of the last of the anshi kinesses hagidolah.
As you can see, there is a large gap in Kellerman's mesorah.
Here is a good link (by a probably frum apologist) on the topic https://www.academia.edu/39443984/The_Case_of_the_Missing_165_Years
ISSUE 10: The Rabbis of Chazal
The list continues with about 22 Tannaim and Amorim, starting with Antigonus of Socho and going until the period of the Geonim. While a few of these people on the list are clearly recorded as sharing a rebbe talmid relationship, many in this list are included despite the fact that we have no record of them ever being Rebbe and Talmud. The Rambam built this list based on 3 (unfounded) assumptions:
If the Gemara list them as serving as Rosh Av Bais Din one after another then we can simply assume that they received the mesorah from their predecessor in office.
In someone at any point in shas quotes a single statement in the name of another person, that is enough to establish them as a rebbe-talmid pair
Any son in shas automatically is considered having received the mesorah from his father.
Honestly, aside from number 3, none of these assumptions are particularly reasonable. Even if they are true, it seems rather bold for Rabbi Kelemen to proclaim that he has an unbroken chain of transmission, when a huge chunk of his chain is predicated on unfounded assumptions.
So there you have it, ten reasons why one should be deeply skeptical of the unbroken nature of our mesorah list