07/27/2009 05:12 am ET Updated May 25, 2011

Michael Jackson, Elvis and Professional Hangers On

They'll Kick You, Then They Beat You,
Then They'll Tell You It's Fair
So Beat It

-Michael Jackson

Michael Jackson and Elvis died too young. They had the same handicap that many people with money acquire, the entourage.

Professional athletes call it "the posse." Many who come up from poverty attract the posse of hangers on and yes-men. The gang hangs on until the money runs out and then latches on to another marker.

I've never understood what kind of person would be a professional hanger on but there seems to be an unending string of applicants.

Even before the bad economy.

Michael Jackson was a unique situation. He was a child star who turned adult mega star. There was never a moment in his life where he didn't attract a large entourage.

I wonder how many in the posse were looking out for him and how many were looking to line their own pockets.

Jackson was rumored to be deep in debt. That should not have happened to a man who made hundreds of millions.

Jackson didn't need a posse. He needed someone to advise him and occasionally tell him no.

The "posse syndrome" is not limited to the rich and famous. It happens to anyone who gets a large sum of money.

I've spent my adult life working with injury victims and lottery winners who come into sudden money. They frequently develop a "sudden posse."

As an advisor, the posse is a difficult army to fight. Especially if one of the posse members hints of "romance."

I tell my sudden millionaires that they just became the hottest item in their city. Some people understand and ward off the money grubbers. Others are like West Virginia Powerball winner Jack Whitaker. He was robbed of $600,000 in cash that he brought to a strip club.

I'm sorry about Michael Jackson. He and I are the same age and it seems like he was always connected to my life. Just like Elvis was for my mother's generation.

I'm not sure how Jackson died but there will be those who point to his entourage as a contributing factor, like they did with Elvis.

Elvis and Michael were adult men who made adult decisions.

I wish the "posse" was not one of them.

Don McNay, CLU, ChFC, MSFS, CSSC is the founder of McNay Settlement Group, a structured settlement and financial consulting firm, in Richmond, Kentucky.

He is the author of Son of a Son of a Gambler: Winners, Losers and What to Do When You When The Lottery. You can write to Don at or read his award winning column at He is a frequent guest on television and radio talk shows.

McNay is a lifetime member of the Million Dollar Round Table.