The Lucky MegaMillions Winner: Really So Lucky?

Sure, at face value, the prospect of becoming an instant half-billionaire seems oh-so-enticing. After all, who wouldn't want to win five hundred million dollars, wiping away your financial worries forever.
According to the Washington Post,

Had you won the whole pot, and invested the $300 million conservatively, Steve Fazzari, an economics professor at Washington University in St. Louis, said you could have expected to collect a nice “salary” of about $7 million “after taxes every year for the rest of your life and the rest of the life of your heirs.”
Put another way, that’s $19,000 a day. Forever. And even a one-third share of that is pretty sweet. “If you put it in perspective, you’re pretty rich,” Fazzari said.

And yet, the article notes that most Lottery winners self destruct, under the crushing weight of money most people wouldn't know what to do with. But I often wonder: as much as I'd love to believe that I'd be among the few that would use the money well, is that really true. Imagine if I really earned 19 thousand dollars a day for doing nothing, for the rest of my life. What then would I do with the rest of my life? That sounds more challenging than it seems.
Most of us tell ourselves that we'd study in Kollel forever. But are we made for that?
OK, we'd spend our time giving away our money. Really? Think it's so easy?
Most of us struggle to reach the 10 percent ma'aser threshold without great wealth. I believe that the spiritual challenges of wealth are far greater than the challenges of poverty. Most of us don't really pass the wealth-spirituality test. (When you have nothing, it's much easier to turn to God and put your faith in Him than it when you have anything and everything you need. We, who have so much, have far more faith in ourselves than we do in the Almighty.) My friend Rabbi Barry Gelman points out that the Jewish people, immediately after reaping the spoils of Egypt, proceed to build a Golden Calf. That didn't turn out so well.

Reading about the incredible jackpot from this past weekend, I'm reminded of an Atlantic article about the problems of the super rich that appeared last year.

Does great wealth bring fulfillment? An ambitious study by Boston College suggests not. For the first time, researchers prompted the very rich—people with fortunes in excess of $25 million—to speak candidly about their lives. The result is a surprising litany of anxieties: their sense of isolation, their worries about work and love, and most of all, their fears for their children.

We joke that we'd love to have such problems. But would we?
Ask yourself this: If you could set your children up so that they never had to lift a finger forever to support themselves, would you? Would they end up happy, or just listless - and ultimately miserable? And if we wouldn't want that for our children, why do we buy tickets trying to win such a life for ourselves?
When I lived in the United States, I used to only buy a lottery ticket if winning would change my life unalterably. I figured I needed to win about 20 million dollars to achieve that goal, so I'd only buy my single ticket when the jackpot went over 40 mil. And yet, in retrospect, perhaps the best jackpot is the one that helps - even a lot - but doesn't change your life in a fundamental way. Pay off your house? Great. Buy a vacation and put away money for your kids' college education? Terrific. But winning enough money that you never have to worry about money again?
Sounds like a blessing, but it might be more trouble than we bargain for.