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Many people misunderstand this vital prophecy. Some erroneously believe that the references are to two historic figures who lived and died 2000 years ago (i.e. Jesus/Yeshua and John the Baptist). This is clearly not possible however as the prophecies concerning them did not come then and has not since. It should be abundantly clear to all that thus far the key prophecies concerning HaMashiach (THE Messiah) have not been fulfilled by anyone. Likewise the prophecies concerning Mashiach ben Yosef have clearly not been fulfilled by anyone yet. Lately however I've read a few people using this two messiahs idea to support beliefs that the Bible and all of our sages reject. This is causing some confusion so it might be helpful if I address this. As always your questions, comments, and corrections are invited here or my Jewish-Christian Dialogue group.

First, understand that the Hebrew word מָשִׁיח‎ (mashiach) is used for many different people and even items. This (i.e. M-SH-CH) is a primitive root meaning to rub [something] with oil. Implicit in this is the idea of anointing or consecrating; it also means to paint in certain usages.

The word has a wide variety of applications. For example see:

Exodus 29:29 And the holy garments of Aaron shall be his sons' after him, to be anointed [Hebrew: mashiach] therein, and to be consecrated in them.
Leviticus 4:3 If the priest that is anointed [Hebrew mashiach] do sin according to the sin of the people
I Samuel 10:1 Then Samuel took a vial of oil, and poured it upon his head, and kissed him, and said, Is it not because the LORD hath anointed [mashiach] thee to be captain over his inheritance.
I Samuel 24:6 And he said unto his men, The LORD forbid that I should do this thing unto my master, the LORD'S anointed [mashiach], to stretch forth mine hand against him, seeing he is the anointed [mashiach], of the LORD.
II Samuel 23:1 Now these be the last words of David. David the son of Jesse said, and the man who was raised up on high, the anointed [mashiach] of the God of Jacob, and the sweet psalmist of Israel, said...
Isaiah 45:1 Thus saith the LORD to his anointed [mashiach], to Cyrus...

According to the Bible and our respected elders there is also the teaching that one day HaMelekh Mashiach (The Anointed King) will come, restore Israel and bless all inhabitants of the Earth through the Jewish people (Genesis 12:3). Rambam lists this belief as one of The Thirteen Pillars of Jewish Religion. We Jews want מָשִׁיח! Each morning religious Jews around the world pray the Shemoneh Esrei. The fifteenth Blessing is Malkhut beit David: our supplication that HaMashiach will arrive and restore the Davidic reign:

ES TZEMACH dovid avd'cho m'hayro satzmi-ach,
v'karno torum bi-shu-osecho,
ki li-shu-os'cho kivinu kol hayom.
Boruch ato Adonoy, matzmi-ach keren y'shu-o

"The offspring of Your servant David may You speedily cause to flourish,
and enhance his pride through your salvation,
for we hope for Your salvation all day long.
Blessed are You, HASHEM, Who causes the pride of salvation to flourish."

       * This is taken from the Seif Edition Artscroll Transliterated Linear [Orthodox] Siddur.

As Jews we await "The offspring [singular] of Your servant David": Mashiach ben David. Judaism of course is very diverse but this is the traditional understanding.

HaMashiach will be a fully human, Torah observant, Jewish man who will lead HaShem's people (all 12 Houses) and fulfill the various prophecies at the conclusion of the Olam Hazeh or current age. I discuss these prophecies here, here, and elsewhere. Melech HaMashiach ben David will be a single, divinely anointed, Israeli ruler from the House of David and the Tribe of Judah, who meet ALL of the biblical require,requirements. Thus far no one has succeeded at this. May he come soon!

Our prophets and rabbis explain that HaMashiach ben David will come in one of two ways: either through the collective repentance of the Jewish people, or through divine coercion. The later applies when we speak of the two mashiachs as we will see as we continue. This is not the preferred way for HaMashiach to come! But it appears to be the way it will happen.

In this second scenario, Mashiach ben Yosef and Mashiach ben David will both appear on the world stage. The former will be 'a messiah, the later will be the Messiah. Together they will vanquish the enemies of Israel and establish Kingdom of Zion throughout all of Eretz Y'Israel, all of the Land deeded to Avraham, Isaac, Jacob, and the people of Israel. Their individual tasks will be different but harmonious

According to Rebbe Nachman of Breslov:

Mashiach will conquer the entire world without firing a single bullet.
    -- Siach Sarfey Kodesh 1-67

The real Messiah will be a King of Profound Peace and Righteousness. His personal holiness and his great wisdom will inspire the entire world to Peace and Faith. The Gentile nations will voluntarily come to him seeking his wisdom and leadership.

HaMashiach's main weapon will be prayer!
    -- Rebbe Nachman, Likutey Moharan I, 2

Despite this, the sages are clear that before King Messiah ben David establishes global peace there will be extremely difficult times. We may well be witnessing the birth pangs of these day now (Sanhedrin 98b). Mashiach ben Yosef will oversee and subdue our enemies during these difficult days. All of the negatives of these prophecies concerning him could be avoided however if only the Jewish people would choose to submit themselves to HaShem with emuna (active faith).

Aish.com's Rebbetzin Tziporah Heller and Sara Yoheved Rigler shed additional light on this topic, and what we should each do to prepare (emphasis mine):

We know from the Prophets that the Messianic age will advance in two stages: the first is to be led by Mashiach, son of Joseph [Yosef], and the second by Mashiach, son of David.

The Gaon of Vilna, the great 18th century sage, in his book Even Shleima, writes about the era of Mashiach, the son of Joseph, as the era of the physical return to the Land of Israel. This era precedes the spiritual repentance of the actual Messianic age, that of Mashiach, the son of David.

There is a hiatus between the period of Mashiach the son of Joseph and the revelation of Mashiach the son of David...

The Biblical prophecies of the latter Prophets describe a horrendous time, when all the nations will come up against Jerusalem. These can be interpreted on various levels. For example, the nations coming up against Jerusalem could be fulfilled by condemnations from the United Nations, rather than a literal war. The only thing that is clear from the Biblical prophets is that this period will be very difficult, and that how it plays out will depend on us and our repentance.

What should we be doing during this particular time period? The Talmud in tractate Sanhedrin (98b) says that during the "birth pangs of Mashiach" two things save us: acts of loving-kindness and learning Torah.

By the sovereign will of HaShem, through Theodor Herzl, David Ben-Gurion, the Hovevei Zion, the First Zionist Congress of the Zionist Organization in 1897, and the other early Zionists, the government of Israel has now been re-established. A little over half of the world's Jews have returned home to Israel and more are making aliyah ('ascending' to our homeland) every year. This,we may assume, began the countdown to HaMashiach and the birth pangs of the his yet future Messianic Kingdom. How he will take his reign remains to be seen! That is up to the Jewish people and of course to HaShem.

Continue To Part Two of this study.