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Former East Bay Express editor delves into the super-rich in Jackpot

We would all like to win the lottery, right? After all, in 2019, U.S. residents spent $81 billion on lottery tickets. A sudden windfall would solve all of our problems, by letting us buy a tasteful mansion or pay off that gargantuan mortgage, and getting us out of debt. We would take some fabulous vacations, and maybe try one of those $1,000 cocktails millionaires rave about. There’s nothing wrong with owning a Lamborghini; just don’t park it in the driveway to attract vandals.

Trouble is, the cliché seems to hold—money can’t buy happiness. All it seems to do is borrow trouble. The rich get richer, but they may not be any more content with their incredible net worth.

That’s the premise of Jackpot: How the Super-Rich Really Live―and How Their Wealth Harms Us All, by Oakland writer Michael Mechanic, and newly published by Simon & Schuster.

Senior editor of Mother Jones and former managing editor of the East Bay Express, Mechanic has been a part of the Bay Area’s  journalism scene for nearly four decades. A UC Berkeley biochemistry major who went on to become a Cal Journalism School graduate, he got his start as a summer reporter at the Point Reyes Light, and then took a job at the alt-weekly Metro Santa Cruz. He returned to the East Bay and found work at the Hearst-owned, afternoon San Francisco Examiner and copy edited on the side for the bimonthly Mother Jones.

Mechanic joined the tech-centric magazine The Industry Standard at its peak, when there were enough ads to publish two issues a week. After The Standard imploded with the dot-com bust, Mechanic took a job with the East Bay Express. He became a senior editor at Mother Jones in late 2008.

Jackpot had been brewing for decades. Mechanic’s original plan was to write a book with each chapter devoted to the story of a big-ticket lottery winner. But it wasn’t until he received a call from a literary agent that he made any forward progress on the project.

“As I found writing this book, lottery winners won’t talk to you,” Mechanic said. “You can’t even find them. They go underground because they’ve been so incredibly besieged by scammers and skeezy friends. The less sophisticated you are with money, the more vulnerable you are to this kind of stuff.”

Jackpot recounts some harrowing tales of disillusioned Lotto winners, but its scope is much wider. Mechanic spoke with private-equity investors, superstar coders, philanthropists, sports agents, lottery lawyers, concierges, bodyguards/nannies and others who either are super-wealthy or cater to the needs of the ridiculously rich.

Mechanic believes we live in a modern Gilded Age, a new era manipulated by contemporary “Captains of Industry,” also called “Robber Barons.”

Mechanic said, “The modern day [representative of] the Gilded Age is Jeff Bezos, and Elon Musk, and so forth. Insane wealth, but in a way the spread of wealth is even wider than at the height of the first Gilded Age. As one source said, the tiers of the economic ladder are getting farther and farther apart. The person on the lower rung can’t even see the upper rung.”

Done right, being rich involves more than laying on a beach, sipping a piña colada. 

“In fact, [a lot of] wealth can suck up your time and energy,” Mechanic said. “It can make you miserable because you’re thinking about it all the time. It’s your constant companion.”

In Jackpot, Mechanic recounts the story of an entrepreneur who sold a company, ending up with $40 million dollars. “He said, when you’re creating a business, you’re caught up in what you’re doing. When you have this big pile of money, your whole mindset shifts. You are fearful of losing this money. He said, ‘you’re fear-based now,’ which really stuck with me.”

Wealthy parents especially struggle with how to raise children with the right values.

“If I have $100 million dollars, how much of it do I leave to my kids?” Mechanic asks. “How much would ruin them and how much would help them? People struggle with this.”

A chapter in Jackpot compares experiences at a local private high school and an Oakland Unified School District high school.

“The education is excellent at a place like Head Royce, and it can be excellent at Oakland Tech, but you have to work to find it,” Mechanic said. “The bureaucracy is awful, but you can still come out of Oakland Tech with a great education.”

Mechanic, whose own kids attend Oakland Tech, said, “I think it’s good for people who send their kids to private schools to understand that [decision] perpetuates inequality.”

As it has everything else, the pandemic has altered people’s perspectives on money.

“Covid has made it hard to deny the privilege of the upper classes,” Mechanic said. “It’s hard to not feel complicit in society’s unfairness once you see how rich people actually got richer during the pandemic while everybody else suffered.”

Mechanic said, however, that he didn’t want to write a polemic. “My views come out in Jackpot, sure, but I didn’t want it to be finger-wagging.”

After all, it can take considerable effort not to be rich. Mechanic points to McKenzie Scott, Jeff Bezos’ ex-wife.

“She was incredibly generous and gave away [about] $8 billion dollars [in 2020], but gained more than that in stock market value,” Mechanic said. “When you’re that rich, you’re making money so fast you can barely give it away fast enough.”

Mechanic learned a few things by studying the ultra-wealthy.

“It made me realize how privileged I am as a white man in America,” he said. “I have enough money to live decently. A lot of people don’t, and I should share that.”

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