The First Way to Perfection, Which is the Renunciation of Temporal Things
Among temporal goods the first we should renounce are external goods, which are called riches, [This renunciation is first, not in the sense of most important, but rather, in the order from imperfect to perfect. It is a basic starting point.] and the Lord counseled this when he said, "If you would be perfect, go, sell what you possess and give to the poor, and you will have treasure in heaven; and come, follow me." (Matt. 19:21). [Principal in the consideration of the evangelical counsels is not our judgment of their utility, but the fact that they are counseled by Christ. Hence Thomas begins with Christ's expression of this counsel.]
St. Thomas illustrates the value of this counsel in two ways. First, by the story of the rich young man who received the counsel, and what happened with him. The young man went away sad, being too attached to his possessions to give them up in order to follow the Lord more closely. Secondly, by the words of Christ spoken in this context, namely that it is hard for a rich man to enter the kingdom of heaven, and that it is easier for a camel to pass through the eye of a needle than for a rich man to enter the kingdom of heaven. St. Thomas sees the second statement as expressing the impossibility of entering heaven when one has an inordinate love of riches (understood in the sense of loving them in a manner incompatible with their being means to true spiritual goods), and the first statement as expressing the difficulty of possessing riches without one's heart being caught by them.
St. Thomas continues to clarify that it is indeed possible to possess riches without one's heart being attached to them, and gives the example of Abraham, who had much wealth, but was perfect in faith and the following of God. But, he says, the fact that Abraham had wealth without being attached to wealth, indicates the great virtue of Abraham. But most persons, not having this kind of virtue, cannot retain wealth without being attached to it. He restates the case more generally: the rich man who does not sin by the affection for riches, who does not covet money, who does not place his trust or hope in his wealth, is indeed a man of great virtue and love of God; but as great virtue is rare, so such a rich man, who has riches without being attached to them, is very rare.
In the Summa Theologiae (II-II 186:3 ad 6) St. Thomas cites Jerome in support of the position that it is better to give away one's wealth all at once for the sake of God, than to distribute it little by little. Jerome says, "to him who says that it is bettter to have possessions and to divide them gradually among the poor, not I, but God will respond saying, 'If you wish to be perfect etc.'… what you praise is the second or third rank, which we also recognize, as long as we admit that the first rank is preferable to the second and third."
But let's suppose that someone in fact could in the long term help many more poor persons by distributing his wealth in a gradual manner than by giving it all away at once–or even not "distribute" at all, in the sense of simply giving it away; the best use of the wealth might be in running a business in a manner that, by being truly fair to employees, partners, etc., is better for the common good of society than giving away the money would be. What should we say about this case? Is such a man forced to choose between his own spiritual perfection and love for the poor? That would seem to be an absurd conclusion. But how do we bring these two desires into harmony, the desire to be free from possessing wealth so as not to be attached to it, and the desire to do good with the wealth?
Granted that the desire to help the poor springs from and corresponds to true love for them as God's children, we would have to say, in the abstract, that this charity for the poor would have to take precedence. To hold otherwise would be to place a certain form of perfection or means to charity over charity itself.
Realistically, however, the two desires may be quite rarely in conflict. It is possible, for example, to found a charitable organization or to transfer ownership of the wealth or business in question to an existing charitable organization… and if the skill of the original owner were necessary for guidance in the use of it, he could be retained for this guiding role. In giving the money he intends to use for charitable purposes over to an organization, he would give up some control over how it is to be used; he might think this is a bad thing, because the organization might make unwise decisions regarding the use of the money. But in fact, supposing that the leadership is wisely chosen, what reason would the original owner of the wealth have for thinking that he knows better how to put it to good use, or that he will remain firm in his pursuit of noble ends, and not fall in love with some distorted ideology?
It would seem, then, that a rich man might best attain these two goals (making good use of the wealth, and guarding himself from attachment to it or the power it brings) by giving his money or his business to a sound charitable organization, or establishing one. I would hesitate to pronounce definitely on this, however. There are some weaknesses to which organizations are more prone than individuals. For example, an organization tends to be more susceptible to influence by the media than a single individual does. So there might be some situations where it is better for a rich person to retain control of the charitable purposes to which it is put.