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She also, according to the government, evaded sales taxes on expensive jewelry in New York (which has a sales tax) by having the jeweler send empty boxes to Florida (which has no sales tax). As a result, she may have saved several thousand dollars, but she spent more than a year in prison, when she had only a few years left to live and even less time to spend with her dying husband. By any rational calculus, this is crazy behavior.

Mike Tyson, as the world’s greatest boxer, had a limited career ahead of him but virtually unlimited access to sex. As with many famous athletes, women were falling all over him, sending him “audition” tapes, waiting for him wherever he appeared and begging him to have sex with him. Yet, he agreed to be alone in a hotel room with a young woman he had just met and to risk being falsely accused of rape – which, in my view, he was – in order to get even more sex. The result was that he was sentenced to several years in prison near the end of his short career, and lost almost everything he had worked so hard to acquire. Even he later acknowledged to me that he was a “schmuck” for risking so much for so little.

In both of these cases, celebrities risked what they had limited amounts of – in Helmsley’s situation the few remaining years of her life and her time with her husband; in Tyson’s situation the few remaining years of his career – in order to obtain more of what they had unlimited amounts of: money and sex. Of course, neither one expected to be convicted for what they did, but they both engaged in behavior that carried the risk of being deprived of what they had only limited amounts of. No rationally calculating person, weighing the costs and benefits of taking such risky actions, would do so. But these celebrities – and many others who have consulted me – have done just that.

Some of my celebrity clients have also gotten into trouble because they need, or feel entitled to, immediate gratification without sufficiently considering the longer term implications of their conduct, not only to themselves and their careers but to their loved ones, friend and associates. They believe that when the future finally arrives, there will be new quick fixes. And often they are right. Someone generally manages to clean up the mess they left behind. It requires a combination of unlikely factors and some bad luck to produce disaster, since most successful people are good at making problems go away. But even celebrities are subject to the law of probabilities and eventually – if they persist in their reckless behavior – the statistics will likely catch up with them.

Why do so many celebrities act so recklessly? Is there something special about being a celebrity that makes one feel invulnerable to ordinary risks? Are they so accustomed to “getting away with it” that they weigh costs and benefits differently from ordinary people?
Is there a sense of entitlement? Are there expectations that the rules don’t apply to them? Do they feel guilty about their “undeserved” success and want to be caught? Do they surround themselves with groupies who encourage bad behavior and refuse to be truthful with them about the risks? Are temptations placed so readily before them that they become difficult to resist?

One answer may well be that some of them have been doing it all their lives, starting well before they were rich and famous. People often have a hard time changing old habits. I know that no matter how much money I now have, I cannot throw away a tea bag after using it only once. It drives my family crazy to see soggy tea bags in a cup waiting to be reused, but I simply can’t

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