What does Hebrews 5:3 mean?
The first few verses of chapter 5 refer directly to a human high priest, in order to make a point about Jesus. Verse 3 summarizes details given more depth in verses 9 and 10. The context is a continuation of chapter 4. In this passage, the writer of Hebrews explains how Jesus' humanity makes Him suitable to become the ultimate High Priest of all believers. Part of a priest's responsibility is offering sacrifice for sins. In the case of a human high priest, this includes their own moral flaws. Acknowledgement of their own sin is part of how a priest is able to be compassionate and gentle with those he serves (Hebrews 5:2).The writer of Hebrews is not at all confused on whether Jesus sinned. As prior verses show, Jesus Himself had no sin to atone for (Hebrews 4:15), though He experienced human temptation in order to sympathize with us. This same point will be made later in Hebrews, acknowledging this as the one characteristic where Jesus is unlike a typical high priest (Hebrews 7:27).
In the instance of Christ, He sympathizes with us on the basis of His temptations, not His sin. In fact, Jesus' perfect life without sin, in the face of temptation, makes His understanding of sin even greater than that of a fallible person. Only those who can fully support a weight truly appreciate how heavy it is. Those who are weak only experience whatever effort they could exert before they dropped that object. Unless someone can hold a weight without "giving in" to it, they don't really experience all of its force. Jesus experienced our temptations beyond the point where we gave in and committed sin. This means that Christ, being sinless, can truly claim to have experienced temptation more than we have!