Integrity and honor are character traits that are of high value in the kingdom of God. They make a person very wealthy even though at the time they may not have a fantastic financial bottom line. When someone is varying between two stances - which is what this passage called being "crooked," they can have all the money in the world and still be seen as far less successful than the poor man who lives a godly life. God's way of valuing things and people is far different than that of the world.
The word "crooked" is very interesting. The literal Hebrew means, "perverse in two ways." What this describes is someone who is going back and forth between two opinions and two views. According to the Theological Wordbook of the OT this term refers to the twisted and perverting nature of sin. The word was also used to describe how a woman twists her hair for the purpose of putting it in braids. Thus the word came to mean the way that people twist their ways and choices contrary to what God commands and desires. The word is used to describe the way rulers "twist everything that is straight" (Micah 3:9). In a similar Proverb about the need for integrity, this same word is used to describe how fools are perverse in their speech.
Too often the rich think they are beyond the law - or above it because of the influence their money buys in this world. I have several friends who are police officers who have told me again and again that they have far more trouble out of rich people they pull over for speeding than from any other group. They are told that they should give the rich person a warning or nothing at all because of all the people they know in City Hall. They try to throw their influence around to intimidate my friends in law enforcement into ignoring the law - or might we say perverting it. They want my friends to act crookedly. These guys write them tickets seeking to enforce the law - only to have them ignored by those in power when they come to court. Too many of the rich make the mistake of placing their hope in riches and what they provide in this world - rather than in God and the hope of His reward in eternity. I say this not to absolve the poor of integrity issues - because the problem is not money - it is the love of money. I've seen the love of money in every financial category there is. The warning here is to run after integrity and honor - and not allow money to make us think that these things don't matter as long as you are well off financially.
Just an aside here for our mutual benefit. I've heard a saying again and again that grieves my heart. Here is the saying, "Money may not be able to make you happy, but it makes your misery much more bearable." Those who say that are truly deceived. They think that a few years of less miserable riches are worth trading for all of eternity. God does not countenance such foolishness. They are truly deceived because they do not understand that their momentary happiness in their wealth and stuff will actually make their judgment more severe. The Scriptures tell us, "To whom much is given, much is required." Whatever brief comfort they find in their things and their wealth will be infinitely offset by the searing judgment that awaits them for loving the world and therefore not having the love of the Father in them. Again - that was for free - because I'm tired of fools sounding wise to this world when they are only multiplying their foolishness for a judgment that awaits them at the throne of God. True wisdom is seeing the end, in this case eternity, and making sound decisions with God's ways in view.
The poor man walks differently here because he walks in his integrity. The word "walk" is the Hebrew word "halak" which means to come and go, or to walk about. It was a word that was used to describe a flowing river, the blowing of the wind, and the movement of animals of all kinds. It was therefore used to metaphorically speak of the pathways of one's life - and came to mean the lifestyle that one chooses. This poor, wise man has chosen to walk out his life using God's wisdom as his guide. The best way to describe this integrity that the poor, wise man chooses is to walk with all of our heart in the things of the Lord. The word here for integrity was used to describe the way that men like David and Job spoke of walking with a perfect heart. This did not mean these men were sinless - just that they did not want to waver between two opinions and two ways of living. They wanted to live for the Lord with all their heart - all the time.
There is something that God values greatly in this world. But what God values and what men value are two entirely different things. This world does not value living for God and His ways with a whole heart. They might give an honorable mention to the occasional religious person who they admire for a few moments because of their devotion to God, but they do not see this as a way of living for all men. They live for the things of the world - and chase after them with all their heart. But what is highly valued by men of this world is despised by the Lord. He is looking for men whose heart is completely given to Him. How much better it is to be one of these men - regardless of their financial bottom line. It is far better to be that kind of a man and poor - than to be the richest man on earth and only enjoy it for the mere length of a breath - which is how God describes this life in comparison with eternity.