Three groups of people

Jewish Eschatology may have minimal presence is Modern Liberal Judaism, but that doesn't mean Jewish scholars and thinkers haven't addressed it. In fact we see Jewish Eschatology addressed in many places in the Talmud, for example Rosh Hashanah 16b to 17a

ראש השנה ט״ז ב:מ׳-מ״ג

תניא ב"ש אומריםג' כתות הן ליום הדיןאחת של צדיקים גמורין ואחת של רשעים גמורין ואחת של בינונייםצדיקים גמורין נכתבין ונחתמין לאלתר לחיי עולם רשעים גמורין נכתבין ונחתמין לאלתר לגיהנם שנאמר (דניאל יב, ב) ורבים מישני אדמת עפר יקיצו אלה לחיי עולם ואלה לחרפות לדראון עולם בינוניים יורדין לגיהנם

Rosh Hashanah 16b:15

Beit Shammai (in a baraita) says: There will be three groups of people on the great Day of Judgement: One of wholly righteous people, one of wholly wicked people, and one of middling people. Wholly righteous people will immediately be written and sealed for eternal life. Wholly wicked people will immediately be written and sealed for Gehenna, as it is stated: “And many of those who sleep in the dust of the earth shall wake, some to eternal life and some to shame and everlasting contempt.” (Daniel 12:2). Middling people will descend to Gehenna to be cleansed and to achieve atonement for their sins,

ראש השנה י״ז א:א׳-ב׳

ומצפצפין ועולין שנאמר (זכריה יג, ט) והבאתי את השלישית באש וצרפתים כצרוף את הכסף ובחנתים כבחון את הזהב הוא יקרא בשמי ואני אענה אותו ועליהם אמרה חנה(שמואל א ב, ו) יהוה ממית ומחי' מוריד שאול ויעל

Rosh Hashanah 17a:1

and they will cry out in their pain and eventually ascend from there as it is stated: “And I will bring the third part through the fire, and will refine them as silver is refined, and will try them as gold is tried; they shall call my name and I will answer them.” (Zechariah 13:9). This is referring to the members of the third group, who requires cleansing. And about them, Hannah said: “The lord kills, and gives life; he brings down to the grave, and brings up.” (1 Samuel 2:6)

This Talmud portion splits humanity into three groups, creating two different places for them to go. As imaginative as this is, it is also problematic, because it makes no mention of the Olam Haba, the World to Come. So the Tosafot helps us combine these two Eschatological ideas of the Three Groups of People and the World to Come:

תוספות על ראש השנה ט״ז ב:מ״א:א׳

ליום הדין. כשיחיו המתים כדמוכח קרא ואע"פ שכבר נדונו אחר מיתתן בגן עדן או בגיהנם מפני הנפש עדיין יהיה דין אחר אם יזכהו לחיי העולם הבא שהוא קיים לעולם ויש שכבר קבלו דינם בגיהנם ומתוך כך שמא יזכו:

Tosafot on Rosh Hashanah 16b:15:1

The day of Judgment -This is the judgment that occurs when the dead rise, as is apparent from the Pasuk. Even though people were already judged after their death to go to Gan Eden or Gehinnom due to their souls, there is still a judgment whether they will receive Olam Haba which means whether they will live forever. Some of these souls have already received their punishment in Gehinnom, and therefore will possibly merit Olam Haba.

Rashi says very little on this subject, however what he does say is pretty profound. For example he sees the middling group has half good and half bad. If they are exactly half and half then it makes it a very small group. Does this mean if you are 51% good you are wholly Righteous?

Another contribution that Rashi makes is to break down this word מצפצפים. The word is mysterious and its basic translation is to cry out. But Rashi has a more nuanced definition, suggesting that those who cry need to do so for only one hour, before they are allowed to rise to be sealed for eternal life.

רש"י על ראש השנה ט״ז ב:מ״א:א׳

ליום הדין - כשיחיו המתים:

Rashi on Rosh Hashanah 16b:15:1

The Day of Judgement - When the dead arise

רש"י על ראש השנה ט״ז ב:מ״ב:א׳

רשעים גמורים - רובם עונות:

Rashi on Rosh Hashanah 16b:15:2

The wholly Evil - Those who have many sins

רש"י על ראש השנה ט״ז ב:מ״ב:ב׳

בינוניים - מחצה על מחצה:

Rashi on Rosh Hashanah 16b:15:3

The middling - Half (of good) and half (of bad)

רש"י על ראש השנה י״ז א:א׳:א׳

ומצפצפים - צועקים ובוכים מתוך יסורין שעה אחת ועולין:

Rashi on Rosh Hashanah 17a:1:1

Crying - Those who cry out from their suffering for one hour and arise

Before we move into some modern commentary, a couple of questions. First does the day of Judgment happen collectively to all of humanity or is it an individual experience that each person must under go? Furthermore does it occur while people are still alive or when they die? What order does the Day of Judgment and the World to Come happen? Does the Tosafot let the wholly wicked off the hook by saying that once a soul endures Gehenna they are allowed to be in the World to Come or is the Tosafot just referring to the middling people?

From the notes of Rabbi David Steinsaltz on Rosh Hashanah 16b

Many commentaries address the question of how this statement should be understood, given the reality that many seemingly righteous people die and wicked people live. Some explain that the righteous referred to are not completely righteous but those middling people, who are judged to be more righteous than wicked are consequently sealed for life. The wicked in this passage are likewise not the completely evil but those who are sealed for death. Others explain that the righteous mentioned here are in fact fully righteous, and they are written for life in the World-to-Come but not necessarily in this world.

One final question, what is Gehenna and what is the World to Come? Below are two descriptions of these Jewish ideas.

Description of Gehenna by Ariela Pelaia
Gehenna is not mentioned in the Torah and in fact does not appear in Jewish texts before the sixth century B.C.E. Nevertheless, some rabbinic texts maintain that God created Gehenna on the second day of Creation (Genesis Rabbah 4:6, 11:9). Other texts claim that Gehenna was part of God's original plan for the universe and was actually created before the Earth (Pesahim 54a; Sifre Deuteronomy 37). The concept of Gehenna was likely inspired by the biblical notion of Sheol.
Who Goes to Gehenna? In rabbinic texts Gehenna played an important role as a place where unrighteous souls were punished. The rabbis believed that anyone who did not live in accordance with the ways of God and Torah would spend time Gehenna. According to the rabbis some of the transgressions that would merit a visit to Gehenna included idolatry (Taanit 5a), incest (Erubin 19a), adultery (Sotah 4b), pride (Avodah Zarah 18b), anger and losing one's temper (Nedarim 22a). Of course, they also believed that anyone who spoke ill of a rabbinic scholar would merit time in Gehenna (Berakhot 19a).
In order to avoid a visit to Gehenna the rabbis recommended that people occupy themselves "with good deeds" (Midrash on Proverbs 17:1). "He who has Torah, good deeds, humility and fear of heaven will be saved from punishment in Gehenna," says Pesikta Rabbati 50:1. In this way the concept of Gehenna was used to encourage people to live good, ethical lives and to study Torah. In the case of transgression, the rabbis prescribed teshuvah (repentance) as the remedy. Indeed, the rabbis taught that a person could repent even at the very gates of Gehenna (Erubin 19a). For the most part the rabbis did not believe souls would be condemned to eternal punishment.
"The punishment of the wicked in Gehenna is twelve months," states Shabbat 33b, while other texts say the time-frame could be anywhere from three to twelve months. Yet there were transgressions that the rabbis felt did merit eternal damnation. These included: heresy, publicly shaming someone, committing adultery with a married woman and rejecting the words of the Torah. However, because the rabbis also believed that one could repent at any time, the belief in eternal damnation was not a predominant one.

Definition of Olam Haba from the Jewish Virtual Library
OLAM HA-BA (Heb. עוֹלָם הַבָּא). The term olam ha-ba (literally, "the coming world") in contrast to olam ha-zeh (liter-ally "this world") refers to the hereafter, which begins with the termination of man's earthly life. This meaning of the expression is clearly implied in the statement of R. Jacob, quoted in Avot (4:17): "One moment of repentance and good deeds in this world is better than the entire life of the world to come." The earliest source in which the phrase occurs is Enoch 71:15, which is dated by R.H. Charles (Charles, Apocrypha, 2 (1913), 164) between 105 and 64 B.C.E. A synonym frequently used in place of "the world to come" is atid lavo ("What is to come" or "the future") as in Tosefta Arakhin 2:7. Often also "the days of the Messiah" are contrasted with the life of this world. An example is the comment by the colleagues of Ben Zoma (1:5) on the phrase "all the days of thy life" (Deut. 16:3) that it includes in addition to this world the era of the Messiah.

Strictly speaking the period referred to by the phrase olam ha-ba or its equivalent atid lavo, between which and the present order of things comes the age of the Messiah (cf. Zev. 118b; Tosef. Ar. 2:7; also Ar. 13b), is the final order of things beginning with the general resurrection and the last judgment. According to the Palestinian amora R. Johanan, the golden age of the future pictured by the prophets concerned only the days of the Messiah. As for the world to come, it is said of it, "Eye hath not seen" (Isa. 64:3). His older contemporary, the Babylonian amora Samuel, however, held the view that the only difference between the present time and the Messianic era lay in the fact that Israel's current subjection to the rule of alien empires would cease. The new order of things would, therefore, according to him, first commence after the age of the Messiah was over (cf. Sanh. 99a; Ber. 34b).