Somehow it’s hard to feel bad for this guy.

CNN.com has an article up on Jack Whittaker who won a $315 million Powerball lottery some five years ago and is now wondering if it was worth it:

The jackpot that was the stuff of dreams turned into a nightmare: His wife left him and his drug-addicted granddaughter—his protege and heir—died. He endured constant requests for money.

Almost five years later, Whittaker is left with things money can’t cure: His daughter’s cancer, a long list of indiscretions documented in newspapers and court records, and an inability to trust others.

“I don’t have any friends,” he said in lengthy interview with The Associated Press. “Every friend that I’ve had, practically, has wanted to borrow money or something and of course, once they borrow money from you, you can’t be friends anymore.”

It sounds like he’s had a rough time, but the more you read the more you have to wonder how many of his problems are so much the result of winning the lottery or just bad decisions on his part. To begin with I’m not sure why you can’t still be friends after loaning one of them some money. I still technically owe my friend Bob for the Amiga 3000 I bought off of him over a decade ago, but I digress.

This isn’t a rag to riches story by any stretch of the imagination, though, as Whittaker was already a successful businessman with a pipeline business worth $17 million at the time he won. His family wasn’t exactly hurting for cash and he admits they lived what some folks would consider a lavish lifestyle. What changed with the lottery wasn’t so much the extra money, he opted to take a lump sum of $170 million which after taxes ended up more along the lines of $93 million, but the celebrity that came along with the prize. That’s when he says his problems really started:

Whittaker’s struggles with drinking, gambling and philandering became public, and tales of his transgressions were retold with relish.

His home and car were repeatedly burglarized. At a strip club, thieves broke into his Lincoln Navigator and stole a briefcase stuffed with $245,000 in $100 bills and three $100,000 cashiers checks. The briefcase was later found, with the money.

Whittaker was charged twice with driving while under the influence and sued repeatedly, once by three female casino employees who accused him of assault.

In all, Whittaker says, he’s been involved in 460 legal actions since winning. He recently settled a lawsuit that alleged his bank failed to catch $50,000 in counterfeit checks cashed from his accounts.

Whittaker believes he has been unfairly demonized by the media, which he says exaggerated his problems and helped drive his wife away.

As I said, sounds more like a lot of bad decisions more than anything else. Who leaves a briefcase with $245,000 in their car when they’re at a strip club? Fuck, who leaves $245,000 in their car anywhere? Granted, having his home broken into probably wasn’t his fault, but driving under the influence? Given his philandering it’s not hard to imagine him possibly assaulting casino workers. Initially I’m inclined to assume the identity theft wasn’t his fault until I remember he was dumb enough to leave over a quarter million in cash and checks in his car at a strip club and then I’m not so sure it wasn’t his own bad decision making that led to the ID theft.

The man has tried to do some good as well. He has a foundation he’s set up that doles out money to needy people and he is probably badgered quite a bit as a result of his notoriety celebrity. His company is said to provide with 200 people or so with well paying jobs. Like most folks he has his good side and his bad side.

But it still seems like he’s whining a bit too much in this article. That may be the fault of the reporter, but it’s hard to feel bad for a guy who has enough money that it’s the last thing he has to worry about when he has to confront the problems life presents him with. He can afford the lawyers and the medical treatment for the problems that come along. It’s also possible that it only seems that way to me because I don’t have the same kind of problems or the money that brings them about and perhaps it’s naive of me to think I have the maturity to handle the problems that would come from winning a lot of money, but I can’t help but think I could.

I won’t ask Mr. Whittaker for any of his money as it’s clear he’s tired of being asked, but I wouldn’t mind if one of the tickets I purchase in the near future gave me a chance to put my confidence to the test. At least I’d have the money to deal with whatever problems come along.

Sent along by Bog Brother.

20 thoughts on “Somehow it’s hard to feel bad for this guy.

  1. Reading the comment about how he thinks that once you lend someone money they can no longer be your friend, I got the feeling he was part of the mafia.

  2. I could be wrong, but I thought he had brought the cash filled case into the strip club and was showing it off, which prompted the thieves to target him. 

    There are money problems with the “beggars”, especially if you don’t learn to say no, but it sounds like a lot of his problems stem from bad decisions on his part.

  3. Yeah Right—feel sorry for me!!  I can’t!  he played around—I’d leave him and take some of that money with me.  He had a drinking problem. Was DUI, had 406 legal actions.  Sounds like he doesn’t care to think before he acts. Nope I can’t feel nothing but that stupidity is a way of life.

  4. I am sure that money does not bring happiness but think of the comfort it can buy.  Damn, I would love to be comfortably miserable as opposed to just miserable.

  5. Like anyone I’ve fantasized about what I’d do if I won the lottery.  (I don’t buy tickets though, as that has little effect on one’s chances of winning)

    Basically it would have to be a call to a new job, as the director of a charitable foundation.  I can only wear one suit of clothes and drive one car at a time but would love to do something significant in education research.

  6. Ok it’s fairly easy to believe that some of those law suits were aimed at him because he’s rich, gold diggers don’t just have to marry you for your money anymore

    But yeah, a lot of his problems stem from being a complete and utter [use your imagination, there are a lot of words that fit and i just couldnt choose one]

    “My wife left me because of repeated infidelity” (not a quote, just a gross simplification of part of what he said)

    that’s right up there with the personal injury advert where a complete idiot stood there and told us he spilt hot tar on himself so he sued the company he worked for

    as for if i won the lottery, i’d like to think i’d donate the bulk of it to a worth charity, but i’d more than likely spend it on booze and paternity cases (the paternity cases would come about from the excessive binge drinking, not pre-existing cases)

  7. Someone so obscenely rich is only willing to temporarily lend to his friends? Why would he want back what he probably wouldn’t be able to spend, and not just use his own judgement as to whether or not to give.

    He could hire a few more security guards too if it’s a problem

  8. I pity people who arrive at any condition and do not know what to do..They do not mean to damage others by their actions, but it does happen. It’s called Ignorance and this man had an abundant supply.

    There is a way, that I find unique about the way money should be thought of…Ready, Set, Here we go…

    A. You have to be a ( Do ) that means you are a person that makes things better, because you are who you are. For instance a 5 year old car is
    better because you bought it, or it becomes worse. It’s all about your nature as a person.

    Now the real work begins.

    1. Who are you ?

    Figure it out on your own and be truthful. Are you Educated? Clean? Dirty? Kind? Rude? What are your strengths and weaknesses?

    2. This is what I do.

    As in your work, achievements,

    3. This it what I have.

    As in assets, property, money.
    The trick is, It has to be in a specific order. !,2,3…Not 3,1,2 or any other order.

    Many people that win or inherit money let it define who they are, and what they do. The screw up everything, and in many cases everyone. Many times people they did not mean to harm, are harmed, or in some cases even destroyed.

    In the case of this man and the lottery, he worked hard for what he had. But still fell into the trap after winning. He became 3,2,1 maybe a 2,3,1

    As far as the Lottery is concerned. On a Mathematical or Statistical enviroment.

    If normal size house bricks ( a line ) are placed all the way ( Round Trip ) from Los Angeles California to New York, NY. And I reach down and touch one brick somewhere along the way to or from.A person stands the same chance at winning the Lottery, as touching the same Brick.

  9. My brother calls the lottery “stupidity tax”.  Of course, that begs the question:  where do we draw the line for protecting people from their own stupidity?  Another hard question.

  10. According to Rotten.com’s Library this guy probably isn’t too statistically anomalous after all.  It appears crime and overall bad behavior are part of the territory for many lottery winners.  I still don’t feel sorry for this guy though.

  11. It appears crime and overall bad behavior are part of the territory for many lottery winners.

    I wonder if that extends to lottery players.

  12. Paul: A. You have to be a ( Do ) that means you are a person that makes things better, because you are who you are. For instance a 5 year old car is
    better because you bought it, or it becomes worse. It’s all about your nature as a person

    I really want to make my life mean something. I don’t really care what happens to the world afterwards though, so it is a selfish desire to satisfy my own needs, but then i suppose everything feeling-driven, including the attemt to minimise guilt, is done selfishly because we only feel our own feelings (even if they do link to those of others, we’re doing it just to feel better)

    It meant a lot to hear the quoted, I’ve just got to seek oppertunities, but I don’t know where to start and I’d never have that thirst quenched, maybe it’d be better if I tried not to have that need…

    zilch: where do we draw the line for protecting people from their own stupidity?

    At the point where they harm others or do something irreversable, everything else is a mistake they could learn from and may need to make

  13. zilch: where do we draw the line for protecting people from their own stupidity?

    Bahamat: At the point where they harm others or do something irreversable, everything else is a mistake they could learn from and may need to make

    Wow, that has to be the most profound thing I’ve ever heard Bahamat say. Kudos.

  14. Bahamat

    I really want to make my life mean something. I don’t really care what happens to the world afterwards though, so it is a selfish desire to satisfy my own needs, but then i suppose everything feeling-driven, including the attemt to minimise guilt, is done selfishly because we only feel our own feelings (even if they do link to those of others, we’re doing it just to feel better)

    About the ( Do ) thing. It is not meant to be taken to obsessive compulsive levels. All I am saying is you cannot be lazy to the point that your totally worthless. In other words if a year old bag of potato chips just set and turns green on the floor board of your car, You are probably a ( No DO..) It can go the extreams also, as in Sociopathic behaviorism. or when a person completely does not give a shit about anything except self. Not that your post would indicate that of course. rolleyes

  15. Les – thanx smile

    Paul – I’m a bit of a split personality, I seem unable to care for those I don’t know (who are mere physical obstacles), and yet would fully engage with the same people were I to know them a little.

    I have little emotion (either way) towards anybody, and yet care, but only because of the feelings of guilt I would have otherwise. Since I only feel my own feelings I’d be doing things for other people for the selfish reason of peace of my own mind, or the selfish reason of aquisition of money. Perhaps I’m a slave to my feelings, if I were to try to be neutral towards guilt perhaps I’d be free from other people, and if I was able to tolerate all things that come without money perhaps I’d be free from that.

    Feelings seem the only thing able to give existence any meaning whatsoever, god or no god, existence as a whole wouldn’t mean anything if nobody felt any emotion, and yet, why do we prefer some emotions over others? We know evolution has aligned things to feelings we like and dislike to influence actions, but I don’t understand why people inherantly prefer the feelings that have been associated to (ie imagine if people preferred pain over comfort, evolution would associate hunger to comfort to get people to eat, but there is still no explanation as to why they would prefer pain in the first place)

    Perhaps it’s automatic and random, and that evolution needed 2 polar ends but didn’t care itself which was + and -, but then there’d be no reason for genetic preference of one mode over the other, so what I consider absolute comfort could be what another considers absolute pain, and vice versa

  16. Bagamat, I really appreciated reading your above post. It rings with a deep sense of honesty, I too fall into a certain amount of the same feelings. I do care, but it is on a level that I feel is somewhat isolated. I worked in the Funeral Industry for many years. Yes I care, But shut off the paycheck and it becomes another story. However….If I saw a child fall from a bridge into an icy river, I would make every attempt to save their life, even if it meant that I may lose my own.

    It’s late…Good night zzzzzzz

  17. zilch: where do we draw the line for protecting people from their own stupidity?

    Bahamat: At the point where they harm others or do something irreversable, everything else is a mistake they could learn from and may need to make

    I’ll agree with Les and say that this is a very good goal to aim for, but in practice it’s still hard to draw the line.  For instance: alcohol abuse can be irreversible, but simply outlawing alcohol doesn’t seem to work very well either.  Where do we draw what lines?

  18. Paul – I suppose the situation determines how much someone needs to care, people who are able to care cannot psychologically afford to care all the time (whouldn’t want to be distressed at what’s out of our hands, and wouldn’t cope if we did).

    I think self-interest is not entirely bad, it has to be weighed against that of others (must respect self as well as others), that one should not be expected or feel compelled to sacrifise everything they have for a minor gain for another, nor should the majority sacrifise a larger total than the individual gains, it’s often only adressed from the parasitic side, but I think excessive sacrifise causes more suffering to the giver than the reciever gains, what you wouldn’t expect of someone else you shouldn’t expect of yourself, but also what you expect of yourself you shouldn’t expect of someone else. Be delighted of anything you or others do above expectations, lower your expectations to be more delighted.

    You know in yourself if you need to shift attention towards yourself or others

    Zilch – I see what you mean, that things not easily pinpointed in time as events, that occur to differing extents are subjective. An alcholhol abuser would probably recognise it as a mistake, but I think whether or not they give it up boils down to willpower, which is not always at it’s peak with those who allow themselves to get addicted.

    I think given enough time and the right situations (which is a matter of time) most people whould eventually find the willpower to quit (as with drugs), death can intervene before this point is reached – but perhaps death could be taken out of the equation/ignored for purpose, because it doesn’t matter if someone had an alchol problem once they nolonger exist, their alchohol problem would’ve disappeared with them, they nolonger factor in – and (for sake of arguement) if they did somehow continue existing afterwards, they would either have more time to get over it (cold turkey perhaps), or immediate resolution, so however it goes death does not keep someone eternally addicted, and it isn’t truely permanent if you are not permanent yourself.

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