Anyone wanting to walk in the shoes of disgraced financier Bernard Madoff was in luck, as thousands of belongings from his New York penthouse, including pairs of designer shoes, recently went on the auction block, and often sold for far more than the pre-bid estimates.

Madoff loved footwear. He owned about 250 pairs of designer shoes, mostly European imports. Ten pairs of Madoff’s used designer shoes sold at this auction for the steep price of $900, well exceeding the $250 minimum.

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Madoff was also fond Italian house slippers and possessed numerous embroidered sets. The slippers, bundled with a shirt and some other items, went for $6,000, against a pre-sale value of $110. The purchaser said he would never be able to wear the slippers because his shoe size is 13, far larger than Madoff’s 8.

Other noteworthy items for sale included a 10.5-carat diamond engagement ring that belonged to Madoff’s wife, Ruth. The winning price was for $550,000. Bernie’s vintage steel Rolex watches sold for $67,500.

Madoff was arrested two years ago for running a multi-billion dollar Ponzi scheme in which he used billions of dollars in cash from new investors to pay old ones, cheating charities, celebrities and institutional investors, many of whom were Jewish. The disgraced 72-year-old is behind bars for life in prison; his wife was unceremoniously ordered to leave their homes. Advertisement

I am fascinated by the continued enthrallment with Madoff and so I sought to identify basic motivating factors that likely played a central role in the frenzied, top dollar purchasing of his belongings.

On the simplest level, the auction gave people the opportunity to establish a connection with the rich and famous, to enter a realm (albeit vicariously) that is seldom experienced by even some of the world’s most affluent individuals. Despite the fact that many items comparable to those that were auctioned could have been purchased for less elsewhere, the idea that they once comprised a segment of the once-glamorous Madoff estate motivated buyers to pay top dollar for a piece of someone else’s past glory.

Others, such as John Rodger, were motivated by their chance to be part of history. Rodger, an 81-year-old Long Island real estate executive, purchased a 1917 Steinway grand piano at the auction for $42,000. “I’ve got loads of pianos, but this one has history,” he said. “It’ll make an interesting conversation piece.”

Still, I suspect that at least some of the bidders were attracted by a desire to connect with the fantastic, debased nature of the Madoff scandal.

We are all aware that each person is born with a capacity for good and the ability to stray down the path of evil. For the most part, we stay somewhere within a normative range of behavior and thought, and choose to conduct a life that is either generally righteous or moderately sinful.

In every generation, however, there also exist individuals who achieve lives of notable piety, or, conversely, descend to the depths of extreme decadence. Such people garner our attention due to their unique status on the moral continuum, and typically either earn our collective adulation for their noble character and deeds or are the source of our shared disdain for their sinful, wicked conduct.

Yet sometimes the exact opposite occurs. Instead of admiring the righteous for their goodness, we allow the evil side within us to overtake our intellectual awareness and belittle their pious achievements. Conversely, there are times when we are confronted with evil and instead of reacting to the murderer or swindler with abject disgust and anger, an unexplainable sense of admiration creeps in, suggesting an element of regret that we were unable to achieve that same degree of vice ourselves.

Our sages (Sifri 32) inform us that when we are instructed to love Hashem “with all [of our] heart” (Deuteronomy 6:5), it means we must “love Him with [our] two inclinations [the good and the evil].” Rabbi Samson Raphael Hirsch suggests that this obligation places a tremendous moral obligation on every Jew, one that forces us to be in complete control of all our impulses.

To “love God with all your heart,” with both yetzer tov and yetzer hara, means to consecrate all of our thinking, together with all of our tendencies and impulses, all of our potentialities and endeavors without reservation to the fulfillment of God’s will, and to control and use them in His service in such a manner that will bring us nearer and nearer to Him. [Hirsch Siddur, Feldheim, pg. 116]

Certainly this can be a great challenge, especially as we witness those who have lived sinful lives and repeatedly tasted the sweet benefits of their illicit labors. In fact, American society routinely glamorizes such individuals, despite the tragic turns that their lives often take, such as life imprisonment and seizure of their many possessions.

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Rabbi Naphtali Hoff, PsyD, is an executive coach and president of Impactful Coaching and Consulting. He can be reached at 212-470-6139 or at [email protected].