Gary Webster: Av - Hidden Connections Between Jesus, Tisha B’Av, and Isaiah 53 [2025/5785]

Shalom from Jerusalem, the one and only eternal city. Tonight begins the month of Av. It is a sad month. It is a month for reflection. It is a month to be consoled.

If you know anything about Jewish history, then you know why this month is a sad month. On the 9th of Av, traumatic things happened to the Jews. The ten spies brought back their evil report on the 9th of Av. The temple which Solomon built was destroyed on the 9th of Av. The temple that Herod renovated was destroyed on… yes, the 9th of Av. Whenever something is repeated in the Bible, it should cause us to pay attention. G_d wanted the nation of Israel to pay attention.

Why did these and other events happen on that day? That is a discussion for another night.

I would like us to travel back in time to a Tisha B’Av over two thousand years ago. The setting is the Jordan River near the Judean Desert. The characters are a prophet called John and his cousin Jesus of Nazareth. John is immersing people in the Jordan River. It is a baptism of repentance. Jesus (Yeshua) will also be immersed but for other reasons. He will then go into the desert where He will be tempted by Satan for forty days and nights.

Do you remember who also went through a forty-day ordeal? Correct. Moses and Elijah — the same gentlemen who meet Him on the Mount of Transfiguration.

What sustains Yeshua during that forty-day test?

The Word of G_d. Specifically, the words from Deuteronomy (Devarim). Let us turn to Luke chapter 4:

Then Jesus, being filled with the Holy Spirit, returned from the Jordan and was led by the Spirit into the wilderness, being tempted for forty days by the devil. And in those days He ate nothing, and afterward, when they had ended, He was hungry.
And the devil said to Him, “If You are the Son of God, command this stone to become bread.”
But Jesus answered him, saying, “It is written, ‘Man shall not live by bread alone, but by every word of God.’”
Then the devil, taking Him up on a high mountain, showed Him all the kingdoms of the world in a moment of time.
And the devil said to Him, “All this authority I will give You, and their glory; for this has been delivered to me, and I give it to whomever I wish. Therefore, if You will worship before me, all will be Yours.”
And Jesus answered and said to him, “Get behind Me, Satan! For it is written, ‘You shall worship the LORD your God, and Him only you shall serve.’”
Then he brought Him to Jerusalem, set Him on the pinnacle of the temple, and said to Him, “If You are the Son of God, throw Yourself down from here. For it is written:
‘He shall give His angels charge over you, to keep you,’
and,
‘In their hands they shall bear you up, lest you dash your foot against a stone.’”
And Jesus answered and said to him, “It has been said, ‘You shall not tempt the LORD your God.’”
Now when the devil had ended every temptation, he departed from Him until an opportune time.

Why did Yeshua use Deuteronomy to rebuke the Devil? I believe it had to do with the events taking place on the Jewish calendar.

During those six weeks that Yeshua is in the desert, synagogues throughout the then-known world were reading portions from this book every Shabbat. They were also reading portions of Isaiah the prophet. The Shabbat before Tisha B’Av, Deuteronomy chapters 1–3 and Isaiah chapter 1 are read. The next Shabbat, Isaiah chapter 40 is read. The opening words are:

“Comfort, yes, comfort My people!” says your God.
“Speak comfort to Jerusalem, and cry out to her, that her warfare is ended, that her iniquity is pardoned.”

The Shabbat before Rosh Hashanah, Isaiah 61:10 to 63:9 is read.

There are two curious omissions from the Haftorah readings. Isaiah chapter 53 is NOT read. Why? I will address that momentarily. The second omission is that the first nine verses of Isaiah 61 are not read.

It was read during the time of Yeshua. In Luke chapter 4, it states that Yeshua returns to the Galilee after His temptation is over. He goes to the synagogue in Nazareth on Shabbat. He is given the scroll of Isaiah to read. He reads from Isaiah 61:

“The Spirit of the LORD is upon Me,
Because He has anointed Me
To preach the gospel to the poor;
He has sent Me to heal the brokenhearted,
To proclaim liberty to the captives
And recovery of sight to the blind,
To set at liberty those who are oppressed;
To proclaim the acceptable year of the LORD.”

Then He closed the book (scroll), and gave it back to the attendant and sat down. And the eyes of all who were in the synagogue were fixed on Him. And He began to say to them,

“Today this Scripture is fulfilled in your hearing.”

As you study the life of Yeshua, you see He did all this and more.

Did the rabbis who came after Yeshua not want their people to know this about Him? Leaving out some verses is one thing — but leaving out a whole chapter is another.

Isaiah 53 is the penultimate description of the suffering Yeshua underwent during His last Passover on Earth. Not everyone agrees with this view. The Jewish commentaries about this chapter say it refers to the nation of Israel and all that they have suffered during the ages.

Acts chapter 8 in the Brit Chadasha might shed some light on this controversial chapter. Philip is directed by the Holy Spirit to take a detour. He is to leave where he is, Samaria, and go to some place on the road going from Jerusalem to Gaza (the same place where the IDF is fighting). When he gets there, he meets an important person from Ethiopia who had come to Jerusalem to worship and was going back home. This nameless eunuch is reading a passage from the Isaiah scroll. What is that passage? Isaiah 53.

Let’s pick up from the story:

Then the Spirit said to Philip, “Go near and overtake this chariot.”
So Philip ran to him, and heard him reading the prophet Isaiah, and said, “Do you understand what you are reading?”
And he said, “How can I, unless someone guides me?” And he asked Philip to come up and sit with him.
The place in the Scripture which he read was this:
“He was led as a sheep to the slaughter;
And as a lamb before its shearer is silent,
So He opened not His mouth.
In His humiliation His justice was taken away,
And who will declare His generation?
For His life is taken from the earth.”
So the eunuch answered Philip and said, “I ask you, of whom does the prophet say this, of himself or of some other man?”
Then Philip opened his mouth, and beginning at this Scripture, preached Jesus to him.

This learned man understood what you and I understand. The suffering servant is a person, not a group. He is Jesus (Yeshua).

May I suggest you get a copy of the Torah/Haftorah cycle for this year? Read the passages from Deuteronomy and the corresponding passages from Isaiah. When you get to Parasha Shoftim, read Isaiah 52:12 to 53:12 instead of what is listed. For Parasha Nitzavim, read from verse one of Isaiah 61.

Ask G_d to speak to your heart as you read. May you come to say like that Ethiopian eunuch, “I believe that Jesus Christ is the Son of God.”

Rosh Chodesh Sameach!