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After Yochanan served as the Kohen Gadol for 80 years, he "left the fold" (Berachos 29a)

ולא והא תנן אל תאמין בעצמך עד יום מותך שהרי יוחנן כ"ג שמש בכהונה גדולה שמנים שנה ולבסוף נעשה צדוקי

The Gemara asks: And does he not become wicked? Didn’t we learn in a mishna: Do not be sure of yourself until the day you die, as Yoḥanan the High Priest served in the High Priesthood for eighty years and ultimately became a Sadducee. Even one who is outstanding in his righteousness can become a heretic.

What caused him to leave Judaism?

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Yochanan didn't leave Judaism; he became a Sadducee, meaning that he left the Pharisees. If we follow Abbaye's opinion that Yannay is Yochanan (Berachot 29a), then the story of how he became a Sadducee is given in Kiddushin 66a. Rava's opinion is that they are two separate people, but the story is still useful because it explains the motives why someone might convert from being a Pharisee to being a Sadducee. Here are the relevant parts of the story (translation modified from Sefaria):

היה שם זקן אחד ויהודה בן גדידיה שמו ויאמר יהודה בן גדידיה לינאי המלך ינאי המלך רב לך כתר מלכות הנח כתר כהונה לזרעו של אהרן שהיו אומרים אמו נשבית במודיעים ויבוקש הדבר ולא נמצא ויבדלו חכמי ישראל בזעם ויאמר אלעזר בן פועירה לינאי המלך ינאי המלך הדיוט שבישראל כך הוא דינו ואתה מלך וכהן גדול כך הוא דינך ומה אעשה אם אתה שומע לעצתי רומסם ותורה מה תהא עליה הרי כרוכה ומונחת בקרן זוית כל הרוצה ללמוד יבוא וילמוד

Now there was a certain elder present called Yehuda ben Gedidya, and Yehuda ben Gedidya said to King Yannai: King Yannai, the crown of the monarchy suffices for you. Leave the crown of the priesthood for the descendants of Aaron. As they would say that Yannai’s mother was taken captive in Modi’in. And the matter was investigated and was not discovered. And the Sages of Israel were expelled in the king’s rage.

And Elazar ben Po’ira said to King Yannai: King Yannai, such is the judgment of a common person in Israel. But you are a king and a High Priest. Is this your judgment as well? Yannai replied: And what should I do? Elazar responded: If you listen to my advice, crush them. Yannai countered: But what will become of the Torah? He retorted: Behold, it is wrapped and placed in the corner. Anyone who wishes to study can come and study. We have no need for the Sages.

In other words: a Pharisee insulted him by claiming that he wasn't a proper priest because his mother was raped, which led him to suspect the Pharisees of intending to rebel against him, and so he expelled the sages. Afterwards, El'azar ben Po'ira advised him that anyone who wishes can come and study the Torah. As Rav Nachman bar Yitschak adds here, his statement that whoever wants to learn the Torah can do so without the sages was a repudiation of the Oral Torah, meaning that he believed that the Written Torah was all that was necessary.

If we follow Abbaye in identifying Yannay with Yochanan, these would be the reasons that led him to become a Sadducee. If we follow Rava, then this isn't directly about the same person, but the motives (disputes with the Pharisees and the belief that the Torah could be learned without the traditions of the sages) could have been similar in his case.

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  • I'd follow Rava on this one for two reasons. First, Yannay was High Priest from 103-76 BCE, give or take a year, so it was nowhere near 80 years. Second, all of Yannay's coins have his name as "Yehonatan"(and possibly "Yonatan"). The only "Yochanon"/"Yehochanan" named on coins are on the ones of Yannai's father, John Hyrcanus, who wasn't High Priest anywhere near 80 years, either. On a few Persian Yehud coins there's "Jochanan", who could've been the High Priest or Governor during that period. – Gary Dec 31 '19 at 2:33
  • I think "convert" is an overstatement. But I stand to be corrected. – WAF Dec 31 '19 at 6:34
  • @Gary I agree that Rava's opinion looks better historically in light of what you mention, but for interpreting the barayta what's important is what the author of the barayta thought centuries after Yannay and Yochanan, so Abbaye's opinion is a valid literary interpretation – b a Dec 31 '19 at 12:26
  • @WAF I meant it in the sense of changing affiliation, not changing religion – b a Dec 31 '19 at 12:26
  • Note that according to Abaye's explanation, the Gemara there in Berachos also points out that he was a רשע מעיקרו (originally a rasha, then did teshuvah), and therefore was more susceptible to regressing. – Meir Dec 31 '19 at 17:46
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A vort from R' Moshe of Kobrin is that after 80 years נעשה צדוקי - he felt himself to be a tzaddik. The implication (in view also of the other teachings on that page) seems to be that this led him to pride and then to going wrong.

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  • The phrase is נעשה צדוקי which means he became a tzeduki, not that he thought himself a tzadik. – sabbahillel Jan 1 at 2:58

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