That this Bennett gambling issue continues to be pressed by the media (and his political enemies) should not be surprising to us. That it opens a door to some serious conversations about virtue and vice also should’t surprise us. What I mean is that because Bennett is a good fellow, because he has taken it upon himself to speak publicly over many years about virtue and vice, because he has even exhorted us to be virtuous and chastized us (individually or as a people) when we haven’t been, this is a great occasion to have a first class national conversation about virtue, vice, liberty and what it means, in short, character. That Bennett’s situation is being taken advantage of by his political opponents (and those who prefer that there never be any public discussion of virtue and vice) is irrelevant. I believe I know enough about Bill Bennett to be able to say that he will not mind if we use this occasion to encourage that conversation and the hope that great good will come from it. One of the best pieces written on this issue is by our own David Foster. I recommend that you study it, and pass it around; indeed, comment on it. It is excellent. 
There was a time a few years ago when I remained silent in one of the many excellent classes taught by Dr. Foster, a vice that I was prone to indulging. Dr. Foster had posed the question of whether or not civilization had progressed or digressed from Greek antiquity, a time when thought was virtuous and excellent. Scholars answered in favor of both premises. They were wrong. The answer is obviously neither. The questions are the same today as they were then. Have we come closer to answering them? No. Have we moved away from the primary questions? Not at Ashland University. So, we continue on the path to understanding.
In the end, I pray that it is not necessary to supplement virtue with vice.
Often our leaders are considered to be hypocrites but they are no more hypocritical than the rest of us--they just have more attention called to their flaws because they are under the spotlight.
Because Bill Bennett is arguably an expert on vice and virtue does this require him to be perfect? Is a psychiatrist 100% mentally healthy? Are nutritionists’ and diet doctors’ bodies void of fat, cellulite and clogged arteries? I think not. It all brings to mind the phrase, "Do as I say, not as I do."
Bill Bennett is someone who’s values we should all aspire to uphold. He is one of the few politicians that cares about the moral fabric of this country. He is humble enough to talk openly about his alleged problem with gambling. He is to be commended, admired and supported.
Why the anonymity? Is it that dangerous to talk about virtue and vice, more so now that the leading advocate of virtue in the country has admitted to a vice?
I think Dr. Foster’s piece is the best yet. He puts Bennett’s views and habits into the broader context of character. I wonder if the key to the puzzle here is what some what call semantics but I believe is a real issue: the question of values. Bennett has popularized the terms virtue and vice, and that’s very good, but I have never felt that he had completely freed himself from the notion that virtues are really values, which means personal preferences rather than objective truths, inescapable aspects of the human condition. That’s because character is not theoretical but practical. We are what we are because of the choices we make, not because of the opinions we hold. We don’t cease to be virtuous altogether if we are not always practicing virtue, but the risk in preaching virtue is that one’s enemies will invariably look for feet of clay. Bennett’s clay feet, as it were, are such not only because he is human (as are we all), but because he has not seen clearly enough how endangered virtue is by false theories, such as personal autonomy. Both Bennett’s speech and genuine commmitment may belie this concern, but the irony of defending traditional virtue is that it may take a more radical approach than Bennett’s that separates genuine virtue from loose talk about values. I hope I am not being unfair to Bennett; nay, I hope I am being unfair, that I am wrong. But in our current moral swamp, a return to first principles and not merely to traditional morality is needed. I know lots of people gamble and it is not against the law; and I believe that Bennett’s gambling didn’t destroy his family. But he did give his enemies--and his protestant friends--unnecessary ammunition. You’re right, Peter. A full and mature discussion is in order.
Values are really just desires. What you value is what you desire when this has been mediated by the extent of your knowledge and concern for the facts of the situation. Supposedly people do whatever they desire, after this has been mediated by the mind which is a simple calculator which converts desire into values. The calculation is made easier by the fact of currency. A concern with Virtue is a sort of bias in favor of developing a particular character. To the extent that developing this character is an imperative, one will shun many things which one might otherwise find expedient. Because of this people will have a different price for the soul/character they buy/sell. The greatest danger is probably not selling your soul to the devil, but rather selling it piece-meal to the highest bidder. In the end a lot of this involves posturing and playing with perceptions, some people think they can buy and sell character depending upon the going bid and ask price. You sell your soul/character to make good money, and you buy it back bit by bit when the price is low, or enough people are watching. (you have an opportunity to give to some cause you have always favoured, or perhaps worse to some cause those around you seem to favor) But supposing one cannot buy and sell character in this way, why also accept the notion that men have clay feet by virtue of being human? Certainly to some extent this is a fact, but only in so far as the human mind is a calculator that convinces us that at least sometimes we can day trade character. Dr. Foster picked up on this when he said, "a famous advocate of virtue for whom virtue doesn’t seem to be enough creates doubt about his view of virtue." When virtue doesn’t seem enough, this is a reflection on the valuation of virtue. In the end the true character of a person is strangely personal, veiled and hidden. When we speak of a persons character we are speaking of the sum of that persons valuations (that we are aware of) concerning all things especially virtue (our conception of it, or perhaps Aristotle’s). The point everyone misses when they discuss the fact that money spent on gambling could have been better used on charity, is that it really boils down to saying that Bennett did not get good enough odds. After all supposing he had won $8 million and donated it to charity. Is gambling intrinsically evil? (certainly not, when only Money is involved, is it any more evil when you lose?) Does it just seem more evil because there appears to be a link to doing this and making wagers with ones character/soul? Supposing gambling is an outlet for the desire to see what one can win given what one is willing to risk. Gambling in Vegas could be a very good artificial substitution for the gambling with character practiced daily by millions of people in the real world. But supposing this is a false distinction based off a false dualism hiding a false confidence at root at pointing to the doubtfullness of all virtue. Character has something to do with what one doubts as well as what one believes. If you can say that this "virtue" is never a gamble, then it seems that you have actual certainty of something. I am not calling your bluff, I prefer to gamble with money.
Well, I would probably agree with Mr. Bennett’s views on social issues and morality. Where I would likely have a strong disagreement with him is with regards to his neoconservative views on issues of war, the state, and foreign intervention.