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We read of three different tests of Jesus `taken'by the Pharisees and the Sadducees at Matthew 22:

""Then the Pharisees went out and laid plans to trap him in his words. They sent their disciples to him along with the Herodians. “Teacher,” they said, ...... Tell us then, ...Is it right to pay the imperial tax to Caesar or not?”......Then he said to them, “So give back to Caesar what is Caesar’s, and to God what is God’s.” When they heard this, they were amazed. So they left him and went away. That same day the Sadducees, who say there is no resurrection, came to him with a question. ........ Jesus replied, “You are in error because you do not know the Scriptures or the power of God. ....He is not the God of the dead but of the living.” ......Hearing that Jesus had silenced the Sadducees, the Pharisees got together. One of them, an expert in the law, tested him with this question: “Teacher, which is the greatest commandment in the Law?”

Sequencing of the three tests: first one on paying of taxes taken by the Pharisees, second one on resurrection taken by the Sadducees and the third one on the most important Commandments taken by the Pharisees suggests that they happened in chronological order, with the fist two happening on the same day. But then, the Pharisees having once failed in trapping Jesus, would not have dared to come back with a fresh trap, at least immediately, just because Jesus had silenced the Sadducees. That implies either that the third test took place much later, or that the first and the third test took place together after the second test. My question therefore is: Did the three tests of Jesus taken by the Pharisees and Sadducees, as mentioned at Mtt: 22 take place in chronological order ? What does the Catholic Church teach about the sequencing of the said tests ?

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    It's generally thought that the Gospels, not being biographies in the modern sense, didn't consider details of timing like that to be important. – DJClayworth Oct 26 '20 at 13:28
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    I agree, however, when two stories are connected by a statement saying "right away" or "immediately after" or "the sme day", I would assume that the Gospel writer meant us to accept the order as reflecting history. So small clumps of stories are often sequenced, but not the ordering of those clumps within the entirety of the gospel. – Paul Chernoch Oct 26 '20 at 16:23
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The detail of the order in which the 'tests' (as you refer to them) are arranged is just one part of the evidence regarding the purpose of each book.

Each of the four gospel accounts is quite clearly covering the period of Jesus' presence on earth according to a certain aspect of Jesus Christ's Person.

That aspect is the purpose of the book - to convey a view of Him.

The four together form a complete revelation. Which is then supplemented by the apostolic doctrine of the epistles and the further Revelation in conclusion.

Each account of the 'tests' conveys a different aspect. And chronology is subservient to the expression of that aspect.

It may be that one of those accounts is in chronological order but which one it is, is not actually relevant. What is relevant is Whom He is and What He is.

For that is the purpose of the four books.

John tells us that such was the activity during that period of time, such the complication of interlocking events, such the extent and profundity of what was happening, that if all were documented in fine detail, then he supposes that the world (of men) itself could not properly contain (in sensible documented form) all the content.

But these are written, says John - that we may believe.

And Luke says that many took in hand to write accounts but they had not the full knowledge to do so. Wherefore, he took the task upon himself.

What we have, is what we are supposed to have.

No more and no less.

It may be that what you have seen (a series of 'tests') was not actually a feature in the mind of the writers as they wrote. That there appears to be a certain 'pattern' may - or may not - be relevant.

What is important is the overall purpose of the four authors - and of the One Author of them all.

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