What does Matthew 16:1 mean?
ESV: And the Pharisees and Sadducees came, and to test him they asked him to show them a sign from heaven.
NIV: The Pharisees and Sadducees came to Jesus and tested him by asking him to show them a sign from heaven.
NASB: The Pharisees and Sadducees came up, and putting Jesus to the test, they asked Him to show them a sign from heaven.
CSB: The Pharisees and Sadducees approached, and tested him, asking him to show them a sign from heaven.
NLT: One day the Pharisees and Sadducees came to test Jesus, demanding that he show them a miraculous sign from heaven to prove his authority.
KJV: The Pharisees also with the Sadducees came, and tempting desired him that he would shew them a sign from heaven.
NKJV: Then the Pharisees and Sadducees came, and testing Him asked that He would show them a sign from heaven.
Verse Commentary:
Jesus and His disciples have returned to the west side of the Sea of Galilee after spending some time in the region of the Gentiles (Matthew 15:21). Matthew next records that Jesus is approached by a group of Jewish religious leaders that includes both Pharisees and Sadducees. This is noteworthy since these two sects did not get along easily. They often openly opposed each other. The Pharisees were Israel's teachers, with the closest connection to the people. The Sadducees held political power and were found mostly in and around Jerusalem. The fact that they approach Jesus together may show that they had unified to oppose this threat to their power and the status quo in Israel.

Based on other incidents, it's clear these men did not come to sincerely ask for evidence that Jesus was the Messiah (Matthew 12:1–2; 9–10, 24). Rather, they came hoping to catch Him doing something for which they could discredit Him or end His public ministry. These men are already aware of many miraculous acts done by Jesus (Matthew 12:13–14, 22), including healing diseases and afflictions, and casting out demons. Ignoring all evidence, while asking for more, is a sign of dishonesty.

Performing at the beck and call of hardened skeptics is not part of Jesus' mission; He will not satisfy their request.
Verse Context:
Matthew 16:1–4 describes Jesus' confrontation with a group of Pharisees and Sadducees asking for a sign from heaven—a miracle. He points out that they can read the signs of the weather, but stubbornly won't recognize the signs He has already performed. The demand for even more evidence, when so much is already provided, is the sign of a spiritually bankrupt approach. The only sign Jesus tells such people to expect is the sign of Jonah. This is a reference to His impending death, followed three days later by resurrection.
Chapter Summary:
A group of Pharisees and Sadducees demand a miracle from Jesus, though He has already performed many. Jesus refuses and warns the disciples to beware of the teachings of these religious leaders. Jesus asks the disciples who the people say He is, as well as their own opinion. Peter says Jesus is the Christ, and is commended for that statement. Jesus begins to reveal that He must suffer and be killed before being raised on the third day. Peter's attempt to scold Jesus results in a devastating rebuke. Jesus then says all who would follow Him must take up crosses of self-denial.
Chapter Context:
Matthew 16 finds Jesus returned from the Gentile regions, only to be immediately confronted by another group of Jewish religious leaders. Yet again, these men prove they are insincere: no amount of evidence will ever be enough for them. After a dramatic discussion about Jesus' role as Messiah, Jesus indicates that those who would come after Him must take up their crosses and follow Him. His references to some seeing the Son of Man coming in His kingdom will be fulfilled at the beginning of chapter 17, in an event known as the transfiguration.
Book Summary:
The Gospel of Matthew clearly shows the influence of its writer's background, and his effort to reach a specific audience. Matthew was one of Jesus' twelve disciples, a Jewish man, and a former tax collector. This profession would have required literacy, and Matthew may have transcribed some of Jesus' words as they were spoken. This book is filled with references to the Old Testament, demonstrating to Israel that Jesus is the Promised One. Matthew also includes many references to coins, likely due to his former profession. Matthew records extensive accounts of Jesus' teaching, more than the other three Gospels.
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