The phrase “money doesn’t buy happiness” was probably coined by someone who squandered all their money through a series of really bad and downright dumb decisions. As you will see in this article, many of them were basically better off living like us regular folks; their greed quickly got the best of them, leaving them worse off than they started: broke. So for one reason or another, here are five people who just could handle being rich.

1. “Spend, Spend, Spend!”

Football, or soccer, is a big deal in Britain and much of Europe as well. Because of this, many people will engage in betting and before online gambling became a thing, they would wager small amounts through a system called “football pools.” In 1961, a poor woman named Viv Nicholson tried her luck and before she knew it, was the winner of over £152,000 or over 3 million today’s money. Instead of wisely spending the money on their four children, Viv and her husband Keith said they would “Spend, spend, spend” every single penny. And so they did, until there was nothing left!

2. Sky High to Rock Bottom

David Lee Edwards was a life-long armed robber who spent just one-third of his 46 years in prison. Down on his luck, he borrowed some money from a friend to pay a utility bill and used the remaining cash to buy some pizza and lottery tickets. Edwards was now the winner of a $27 million jackpot! He claimed that he would turn his life around but instead splurged his newfound money on a pricey mansion, expensive gadgets and even narcotics. Edwards later died penniless in a Kentucky hospice at the age of 58.

3. Too Much of a Good Thing

In 1998, Gerald Muswagon, a friendly but not well-educated Canadian native bought a two-dollar lottery ticket that would forever change the course of his life. He instantly became the winner of a $10 million jackpot, and wasted no time spending it on luxuries and gifts instead of investing in his own lumber business. Unfortunately for Muswagon, the business sales tanked and not a single one of his peers advised him on how to handle such a large sum of money.

4. From Bad to Worse

Prior to winning the lottery, Jack Whittaker was an already wealthy and successful businessman in the construction industry. But in 2002, he gained an additional $315 million but opted for the one-off cash payment option which left him with a little over $113 million after taxes. Being the kind-hearted Christian man that he was, Whittaker spent much of his money on charities and foundations to help the poor. His later life took a sudden turn for the worse after he was robbed of over $500,000 from his car, then his granddaughter turning up dead, his house burning down, not to mention his gambling issues.

5. Madame Mayor

San Diego native, Maureen O’Connor, was a successful politician who served as the city’s first female mayor from 1986 to 1992. In addition to her already hefty salary, O’Connor was also the recipient of $40 to $50 million following her husband’s death in 1994. However, she had a secret gambling addiction which led to her losing around $13 million in casinos. She then further misappropriated over $2 million from her husband’s charitable foundation on none other than poker. O’Connor took her addiction a step further by liquidating all her savings and taking out a second and third mortgage on her home.