Jesus, as a human being like us, was able to make choices freely (assuming one believes in "free will" as it is commonly understood), and yet he was presumably without sin (Hebrews 4:15, 2 Corinthians 5:21). Never once during his life did he do anything wrong. But does it not seem suspicious - a little too coincidental - that Jesus alone never did wrong, while all other human beings make wrong choices every day? Was he really free to choose what was wrong? Did he really subject himself to the temptation to sin (Hebrews 4:15) and thus identify fully with humanity?
Here, I think, it is helpful to remember that Jesus, while being man, was also God. Since sin is an offense against the moral value or standard that is inherent to God's being, it is wholly contradictory with his character. God would never sin, or else he would not be God. And if we believe Jesus is the second person of the Trinity, then he would not sin, or else he would not be Jesus. It may then seem that Jesus cannot sin, but what is preventing him from sinning? No cause or force external to himself prevented Christ from sinning. He choose freely to do what was right and just - to live in step with the Father's will - and although he did so infallibly because it was in his divine nature to do so, he nevertheless chose freely, unconstrained by any external force.
One might respond that, by being God, Jesus "cheated" in withstanding temptation as a man, and that consequently he did not fully identify with humanity. The question, then, is whether God's nature, which results in his not sinning, is at odds with human nature. In other words, is the possibility of sinning - of going out of God's will - an essential aspect of human nature? It may seem so, but perhaps this is only so because that is what free will means for any being whose nature was not wholly contradictory to sin - any being other than God. In other words,
"free will + not being God = possibility of sin"
We must distinguish between the possibility of sinning and free will. Perhaps it is not the possibility to choose wrongly per se that is essential to humanity, but free will. What is necessary for the possibility of choosing to sin is both free will and not being God (see above "equation"). Any human except for Jesus satisfies these two requirements, but Jesus, according to Christian doctrine, is both man (and thus has free will) and God (and thus is not among those beings that are not God). In other words, if it is fair to assume that God's free will is the freedom to act unconstrained by anything outside his nature, and that this freedom is preserved in the man Jesus, then Jesus, being both man and God, can have free will and yet choose infallibly what is right. Indeed, God's nature is not at all at odds with human free will; rather, man's freedom of choice is derived from God's freedom (nothing outside of God constrains his actions or choices in any way).
We might also ask, "is it beyond God to fully assume humanity?" That is, can we really say with any confidence that God would be unable to identify himself fully with humanity and assume free will as a man? We must retain a measure of intellectual humility when talking about the infinite, transcendent God. For more thoughts on God's power and freedom in making choices, see my post God: Incomprehensible and Omnipotent.
Jesus is not less with us because he was not bound to sin. He was not constrained to holiness, but chose it freely, just as we have free will. He was tempted – for example, by the devil, after fasting for 40 days. Jesus was born in a stable and grew up as a carpenter – his life was in many ways like that of any human being. And of course, in the cross we find the fullest expression of the meaning of Emmanuel, “God with us” – on the cross God identifies with the pain and brokenness of mankind to the fullest extent possible.
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