I can’t seem to get my mind off the unfortunate puzzle of poor (literally) Evander Holyfield. A feature in The Atlanta Journal Constitution revealed that Holyfield, who earned $250 million over a storied boxing career, was recently evicted from his home. Here’s the other half of that indignity: Sheriff’s deputies knocked at the door of Holyfield’s 54,000-foot mansion outside of Atlanta and told him that he had 15 minutes to leave the premises!

What am I missing here? Holyfield acknowledged in the story that he had received previous eviction notices. Yet he said he thought he’d somehow be able to work out a deal to dissuade JP-Morgan from taking over his home.

A deal? With JP-Morgan?

Holyfield, mind you, is now 50 years old. Which means that there are likely no multi-million dollar fights scheduled for him down the road. And, too, without the house note that he can’t pay, he is still obligated for $500,000 – each year – in child support payments for 11 children.

So why was he thinking that, against all odds, he would be able to hold onto the crib? Or better yet, why did this man fail to think?

The amazing thing is that Holyfield is not alone. I am struck by how often we hear stories of people who made it to the pinnacle of success, then seemingly dropped off a financial cliff: Michael Vick; Lauryn Hill, Mike Tyson, just to name a few.

I always ask myself, how does this happen? These people employ big-time accountants and lawyers to handle the complexities of their financial affairs. Then what makes so many so susceptible to taking the fall? Are they too trusting of their financial handlers? Could be. Are they too busy to focus on their own affairs? Maybe. Are they so arrogant or egotistical as to think money will never stop rolling in, that they will forever be able to “make it rain?”

I suspect that in each case there was some combination of the above at play. There are recurring lessons that many celebrities fail to learn. If I had to guess, though, I would say that the most important lesson relates to the need to closely monitor the people who manage your money.

America is a great country because, with initiative, you can go from rags to riches. We hear that story all the time. The reality that people – especially the powerful – don’t like folks to dwell on is that America is also poisoned by a national culture of unchecked greed. From corporations on down, if there is a way for someone to cheat you, you will be cheated. I read about it in the papers everyday.

Which means that for those of us who are not celebrities, it’s even more critical to watch our financial backs. Although we have much less to lose than the celebrity millionaires, the fall for us can be just as hard.