Tommy Gilbert: The Curse of Free Money and Easy Living

Thomas Gilbert, Jr.

Thomas Gilbert, Jr., 30, had everything. His father was a Wall Street multimillionaire. He grew up amid wealth and luxury. He had attended the best private schools, and graduated from Princeton University in 2009 with a degree in economics. He was 6’3″ tall, healthy, good-looking, and flitted about the high-class society scenes with beautiful women on his arm.

Just one problem.

He didn’t have a job.

Why should he, when his $3,000 a month allowance from his wealthy father paid his rent and gave him some pocket money? He preferred to hang around his father’s multimillion-dollar mansion in East Hampton, NY, hit the gym, do some yoga, and then go surfing.

He did try to start a hedge fund like his father, but it didn’t get very far. He was in debt. And he had no income of his own to match his high-end lifestyle.

Thomas Gilbert, Sr.

After months of tension with his father over the monthly allowance, which his father was starting to cut off, Tommy Gilbert finally took matters into his own hands. He headed over to his parents’ New York City apartment and told his mother, Shelley Gilbert, to go out and get him a sandwich and soda. Once she was gone, he put a bullet in his father’s head and left.

That, anyway, is what all the evidence points to. For more on the story, see these articles at ABC News, the U.K. Daily Mail, and the New York Post.

What went wrong?

Like any story about human beings, this one is complex and many-sided. But one thing seems clear enough: free money and easy living were not a blessing, but a curse in the life of Tommy Gilbert.

A checkered life of privilege

Tommy Gilbert’s arrest on charges of murdering his father was not his first brush with the law.

He is suspected of several other crimes, including the arson of a rival’s home in a dispute over a woman. He was increasingly alone, and had been barred from some of the local hotspots due to bad behavior. When the police searched his home after the murder of his father, in addition to gun paraphernalia linking him to the murder, they found evidence that he was engaging in credit card fraud.

How could someone with all the advantages of life go so wrong?

Perhaps it was precisely because he had everything going for him, without having to earn it, that his life became such a wreck.

Most ordinary people would be ecstatic at the thought of having all that wealth, health, and easy living at their fingertips. But the experience of Tommy Gilbert suggests that what we think will make us happy is not what really will make us happy.

I’m sure Tommy’s parents thought they were doing him a favor by supporting him until he could make it on his own. They were probably mystified by how he could be so wild and so ungrateful after all they had done for him. And he, for his part, had nothing but growing jealousy and anger against his father, even though almost everything he had came from his father’s largesse.

In reality, by continuing to support their son well into adulthood when he should have been going out, busting his butt, and making a living and a life for himself, his parents were doing him a terrible disservice.

Of course, in no way is it his parents’ fault that he murdered his father. Tommy Gilbert still had choices to make—and he made some very bad ones. He must bear responsibility for his own actions. However, by making it easy for their son not to go out and get a real job, they as good as doomed him to waste his life away and accomplish very little of real value.

Money that we don’t work for and easy living provided us for free is almost always a curse rather than a blessing. It tends to make us lazy, dependent, and ungrateful—and in the end, miserable.

The blessing of sweat and labor

The rest of us 99%, who must work day after day to put bread on the table and a roof over our heads, might long for even a little bit of the easy money and easy living that Tommy Gilbert has had.

But would it really be good for us, any more than it was good for Tommy Gilbert?

Our daily work, our labors, and our struggles are the crucible in which our character is formed.

When we first start out in life, most likely we get a job not so much because we want to but because we have to. Most of us don’t have someone supporting us into our adult years. If we want food, clothing, a place to live, and a few of the tangible pleasures of life, we must go out and earn the money to pay for them.

And what do we get paid for?

We get paid to do something for other people.

Yes, there are some jobs that don’t qualify—such as being a hit man or a thief for hire. But for most people, making a living means serving other people’s needs. It might be anything from flipping burgers to typing up letters to managing hedge funds. But if we’re going to make money, we’ll have to do something for somebody besides ourselves.

And that’s why our labors and the necessity of making a living is good for our soul.

If we didn’t have to make a living, most of us would probably spend our days the way Tommy Gilbert did: enjoying ourselves, tending to our body, our social life, and our own pleasures, and not doing much of anything useful for anybody.

But having to go out, get a job, and support ourselves gets us into the habit of working for other people and thinking about other people’s needs. Day after day we get up, go to work, and provide the people in our community with products and services that they want and need.

In doing so, almost in spite of ourselves we begin to be just a little less self-absorbed and self-centered, and a little more aware of other people and their needs and wellbeing.

The joy of service

And the odd thing is, in thinking of others and devoting our lives to their needs instead of only to our own, we start to feel real satisfaction and even joy in life.

Of course, every young man and woman who goes out and gets that first job, buys a car, pays the rent, and supports himself or herself enjoys a sense of satisfaction in finally being a real, self-responsible adult.

However, that satisfaction wears off soon enough. After you’ve supported yourself for a while and gotten used to being out on your own, it ceases to be a novelty, and quickly becomes drudgery instead.

That’s where our choices can make a big difference.

We will put ourselves on a path toward a much more satisfying working life if, as the initial euphoria of independent adulthood wears off, we begin to think of how we can do something good in life, and how we can serve our fellow human beings.

You see, we humans are made to love and serve one another.

In finding and engaging in the particular type of service that we are best at, and that we enjoy the most, we find our true, lasting joy in life.

It might be something great or it might be something humble. It might be cooking and cleaning, or it might be founding and managing a major investment fund for thousands of people. However we are best at serving others, that is where we’ll find our greatest joy in life.

That’s because in serving others, we become the best version of ourselves. It’s what God created us to do, and it is our path toward heaven.

In fact, when we are willingly and happily serving others because we care about them and want to give them happiness, we are already in heaven even while we are still living here on earth.

For further reading:

• Money Can’t Buy Happiness . . . But Service Can
• Is Wealth a Blessing or a Curse?
• The Gold Standard
• What Does Religion Have to Do with My Profession and My Daily Work?
• Heaven, Regeneration, and the Meaning of Life on Earth

About Lee

Lee Woofenden is an ordained minister, writer, editor, translator, and teacher. He enjoys taking spiritual insights from the Bible and the writings of Emanuel Swedenborg and putting them into plain English as guides for everyday life.