How does the Lebanese son of a Mormon mom get indicted for car theft, make a fortune selling car alarms, and get elected to Congress? Just ask California representative Darrell Issa.

OK, OK. Let’s be clear about this: Despite the indictment, Issa has never actually been convicted of car theft. In fact, the prosecutor dropped all charges against him. But as we’ll see, he certainly knew enough about the art and science of car thievery to establish a lucrative car alarm business.

Issa’s origin story was anything but promising. In 1970, he dropped out of high school and joined the army. A member of Issa’s army unit, First Sergeant (Ret.) Jay Bergey, told a reporter for the San Francisco Chronicle that Issa stole his yellow Dodge and took it to Cleveland in 1971. “I confronted Issa,” he said. “I got in his face and threatened to kill him, and magically my car reappeared the next day, abandoned on the turnpike.” Issa, who described Bergey as an alcoholic, categorically denies ever stealing his car. No charges were ever filed.

A month later (in 1971), Issa and his older brother, William, were arrested for allegedly stealing a red Maserati in Cleveland, Ohio. The case was eventually dropped.

Seven years later—in a separate incident—the Issa brothers were indicted for grand theft. The details are confusing, and the case was also later dropped. But as the New Yorker’s Ryan Lizza later described it, the allegation was that “the two men had conspired to fraudulently sell Darrell’s car [a Mercedes sedan] and then collect the insurance money.” The case was also later dropped.

Next, Issa started an electronics manufacturing company called Quantum Enterprises. After one of their client’s loans became delinquent, Issa orchestrated what Lizza calls a “hostile takeover” of the client’s car alarm business, Steal Stopper. According to Jack Frantz, a former employee of Steal Shopper, Issa placed a box containing a gun on his desk before firing him. Issa denies “ever pull[ing] a gun on anyone in my life.”

Then, in 1982, Issa’s manufacturing plant mysteriously burned down. According to the Los Angeles Times, “Circumstantial evidence aroused sus- picion of arson,” and the founder of Steal Stopper alleged Issa was the culprit. “Fire investigators also noted that a computer was taken off the site eight days before the fire, ‘allegedly to be reprogrammed’ by Issa’s lawyer, and that business blueprints were put away in a safe—which was ‘not previously done before,’ ” according to another report from the Los Angeles Times.

Investigators also noted that Issa had dramatically increased his fire insurance just weeks before the blaze occurred. As the New Yorker reported, “The Ohio state fire marshal never determined the cause of the fire and no one was ever charged with a crime. According to Issa, St. Paul [the insurer] paid Quantum twenty-five thousand dollars but refused to pay his claim for the Steal Stopper inventory. Issa sued St. Paul for a hundred and seventy-five thousand dollars, and the two parties eventually settled out of court for about twenty thousand dollars.”

Later, Issa sold Steal Stopper, moved to California, and started Directed Electronics, Inc. His new company produced aftermarket car security products, including the Viper car alarm, where Issa’s own voice can be heard commanding, “Please step away from the car.”

You don’t get to be worth hundreds of millions of dollars without accruing real estate and other investments. But Issa’s fortune was made in the car security business. He then used that accumulated fortune to kickstart his political career in 2000. When reporters started asking questions about his past brushes with the law, Issa responded by throwing brother Bill under the Maserati. “When people ask me why I got into the car alarm business, I tell them the truth,” he said in a statement to the San Francisco Chronicle. “It was because my brother was a car thief.”

That’s right. In a story reminiscent of Frank Abagnale (portrayed by Leonardo DiCaprio in Catch Me If You Can), Darrell Issa, one of the richest members of Congress, a man who formerly served as the chairman of the House Committee on Oversight and Government Reform and is worth approximately $250 million, was accused of stealing cars with his brother (all formal charges against him were dropped)—before making hundreds of millions protecting cars from thieves. For whatever reason, the charges against him kept being dropped.

What does it mean when you can go from such a checkered past to being a member of Congress? One view is that politics is a lateral move— that it’s another type of con and another type of mark. Another view is that Issa achieved the American dream, which often entails redemption and reinvention. Maybe it’s a combination of both.

Many of us have a deep-seated need to rise above humble beginnings and become successful. Could it be the case that this same instinct drives some people to illicit activities and other people to public service (where they can also acquire money and power)?

Issa isn’t the only successful businessperson who wanted to trade in a corner office for the campaign plane. Following is a brief description of a few of the richest politicians in America, and how they got that way.

Greg “The Hammer” Gianforte

Governor Greg Gianforte (R-MT), with an estimated net worth of

$189,334,335, according to OpenSecrets, a nonprofit that tracks money in politics, had a more traditional rise than Issa—before he, too, turned to politics. The son of an aerospace engineer and landlord, Gianforte earned degrees in electrical engineering and computer science. Along with his wife, Susan (also an engineer), Gianforte founded RightNow Technologies, a company that helped pioneer cloud computing in the 1990s. In 2012, Oracle purchased RightNow for $1.8 billion.

Gianforte threw his hat into the political ring in 2016. He lost his gubernatorial bid but rebounded with a win in a 2017 special election for the House. During that campaign, he became infamous for allegedly body slamming reporter Ben Jacobs at his Bozeman, Montana, office. (Perhaps the political ring isn’t the only ring he is familiar with?) Gianforte pleaded guilty to a charge of misdemeanor assault and paid a $300 fine, and he went on to win the election. With an estimated net worth of $189,334,335, he was the richest member of the House of Representatives in 2018.10

Then he ran for governor. In 2020 alone, Gianforte used more than

$4 million of his own money to win Montana’s governorship, as the AP reported. That’s just shy of $4 for every man, woman, and child in Montana—that’s spending big bucks in the Big Sky State. This is a man who has it all.

The Telecom Tycoon

The first in his family to graduate college, Mark Warner (D-VA), whose estimated net worth is $93,534,098, made “his first big money by exploiting a multibillion-dollar government giveaway in the cellphone industry.” In the 1980s, the FCC started awarding licenses to operate cellular franchises by lottery, a seemingly random way for the government to dole out incredibly lucrative licenses—especially because they could be awarded to people who had no interest in the business but who just wanted to turn around and sell the licenses for “in some cases over $300 for each person living in a service area.”

Acting on a tip from a political donor Warner met while working at the Democratic National Committee, Warner began representing a group of sellers. He then acted as a broker—in return for a piece of the action. He parlayed this into joining a venture-capital partnership that focused on the wireless industry. When a cell phone rings during one of his speeches, Warner sometimes jokes, “Most people consider them an annoyance, but I just hear ‘cha-ching, cha-ching.’”

The “McCongressman”

Nowadays, many so-called self-made people earn their fortune in the tech world. But there’s still room for people willing to put in some elbow grease and hustle. One of my favorite examples got to Congress by flipping burgers. Sort of.

Dubbed the “McCongressman,” as Bloomberg noted, Representative Kevin Hern’s (R-OK) wealth (the vast bulk of it) comes from owning a chain of McDonald’s restaurants. Hern is so wealthy that he is richer than the rest of the Oklahoma congressional delegation combined, the Oklahoman reported. Hern’s rags-to-riches story began in Arkansas, where his family lived on food stamps for more than a decade. He had no running water until he was in the eighth grade. He also was born with spina bifida (the same condition that killed his older sister). After high school, he earned a degree in engineering. He moved to Atlanta, Georgia, after being hired to work at Rockwell International, an aerospace firm that had just won a major NASA contract. But the day after he was hired, the space shuttle Challenger exploded. The industry was forever changed, and he was out of a job within a year.

Hern moved back to Arkansas, got a job at McDonald’s, and saved

$100,000—enough to buy his first McDonald’s franchise in Little Rock. Hern’s wealth and restaurant connections were vital to his 2018 election. According to Oklahoma’s Frontier news outlet, a review of donations made to Hern’s campaign in 2018 “show more than half ($705,000) of Hern’s $1.3 million total were loans made by Hern himself or donations by his family members. Of the remaining $656,000 in donations, $129,025 came from fellow restaurant owners, many of whom are McDonald’s franchisees who do not operate in Oklahoma.”

Hern gained notoriety in January 2023, when Representative Lauren Boebert (R-CO) nominated him to be Speaker of the House during the eighth, ninth, and tenth rounds of balloting. Hern “went from rags to riches and, like myself [sic] and many other members, is a small-business owner,” Boebert said in her nomination speech. “He has lived the American dream.” Hern, who cast his votes for Kevin McCarthy, garnered three votes in the ninth ballot. So far, his American dream doesn’t include being Speaker.

The Winemonger

In 2016, Representative David Trone (D-MD), the son of a farmer, lost a congressional race after pumping in more than $12 million of his own money. Two years later, Trone, a wine retailer who co-owns a chain of Total Wine & More stores, finally prevailed. Most recently, Trone was narrowly reelected in 2022, once again spending more than $12 million of his own money to stay in office. As the Washington Post reported, “Trone’s huge financial advantage largely deterred any major investment from national Republicans, leaving [Maryland delegate Neil C.] Parrott to try to pull off an upset with minimal resources. Parrott had raised roughly $800,000 . . .” Trone is a Democrat—but before running for Congress, he gave more than $150,000 to Republicans. Still, give him credit for being honest about it. “I sign my checks to buy access,” he told the Washington Post.

I grew up in Maryland’s sixth district, which Trone now represents, but Democratic gerrymandering has pushed my hometown into the newer eighth district. In any event, Trone stands in stark contrast to the congressman who represented the sixth district for much of my life, Republican representative Roscoe Bartlett, who—according to a 2014 Politico profile—“lives in a remote cabin in the woods, prepping for doomsday.” He and I both ended up living in West Virginia, though he is probably better prepared for a zombie apocalypse. Still, I’d move back to Maryland for Trone’s wine fortune.

The Nepo (Grand)baby

While hard work, smarts, luck, and connections still pay off, it’s also fair to say that many of the richest politicians in America come from wealthy families. One such example is Representative Sara Jacobs (D-CA), who is just 33 years old as I write this. Jacobs is the granddaughter of Irwin Jacobs, the tech billionaire founder and former chairman of Qualcomm.

In 2018, Jacobs joined a crowded field vying to replace Darrell Issa in California’s forty-ninth district. Considering Jacobs was still in her late twenties, it’s no surprise that her résumé was sparse. But according to the San Diego Union-Tribune, Jacobs “exaggerated her work experience” by saying “she was a ‘policy maker’ who worked for the State Department under President Barack Obama.” In reality, Jacobs “was a junior employee working for a government contractor and federal regulations prohibited her from making policies.” She lost that primary election, finishing third.

But you can’t keep the rich down for long. In 2020, Jacobs switched to California’s fifty-third district in central San Diego County, where she faced off against 44-year-old San Diego City Council president Georgette Gómez, a fellow Democrat. The contrast was stark. Whereas Jacobs was a young woman of privilege, the American Prospect described Gómez as “a queer woman of color with decades of community-organizing experience.” Likewise, the Times of San Diego described Gómez’s campaign image as that of an “up-from-the-barrio fighter for social justice who found ways to move San Diego’s needle even with council Republicans’ support.” As Gómez said, “My grocery store was a liquor store, and my playground was surrounded by freeways.”

Guess who won? In addition to the money Jacobs put into her own campaign, her grandparents also spent $1.5 million on a super PAC to boost her 2020 election, as Vox reported. If you want to make it to Congress in your early thirties, it helps to have rich parents (and grandparents).

The pols mentioned above are just a sampling of some of America’s richest politicians. We will meet more of them in future chapters. Regardless, whether they came from hardscrabble backgrounds or were born with a silver spoon in their mouth, any of them could have spent the rest of their lives on a beach drinking piña coladas. And yet, they all decided to run for political office.

The question is, why do rich people want to go into politics?

Some on the left allege that rich people are attracted to politics because they want to rig the system to get even richer. I may be naïve, but this theory doesn’t hold Perrier. To the degree uber-rich businesspeople need to tweak the tax code or kill regulations, it seems like campaign contributions and high-powered lobbying would be more efficient. It’s easier, cheaper, and less déclassé to buy politicians than it is to become one. Don’t underestimate the importance of outsourcing in any American business model.

People who make these cynical accusations also discount the possibility that some rich people believe they are doing a public service and “giving back,” as it were. Depending on your political biases, you could nominate either Herbert Hoover or Franklin Roosevelt for that “honor.” One might say the same for Henry Cabot Lodge or Jack Kennedy. Consider how many rich celebrities love big, flashy examples of philanthropy, like big foundations named after themselves with elegantly furnished offices or star-studded fund-raising events for pet issues. That’s not all done for tax write-offs; the rich often have a desire to give back, coupled with a desire to be in the news for something that isn’t as profit-driven as whatever helped them get wealthy in the first place. It’s not a big jump to get from writing grant checks for medical research to writing (or trying to write) policy that funds medical research. And politics includes public validation, too. After all, you have to get elected, right?

Along those lines, my old college professor Dr. David A. Foltz offers a deep-seated, if esoteric, psychological reason based on the Protestant work ethic embedded before America’s founding. “Success is evidence of salvation, which is predestined for the elect,” he says. How does this “Covenant of Works” explain the desire of rich people to run for office? Having attained financial prosperity, getting elected is further proof you are one of the elect.

Another theory: successful businesspeople become convinced that they can fix public policy because they know how to make money. Translation: they have healthy egos. In my former life as a political operative, I encountered many candidates who had been wildly successful in past careers. They all thought that they could easily apply those lessons to a political campaign. Most couldn’t. I suspect that they similarly underestimate the difficulty involved in governing and legislating.

When General Dwight Eisenhower was considering running for president, the then president Harry S. Truman opined, “He’ll sit here, and he’ll say, ‘Do this! Do that!’ And nothing will happen. Poor Ike—it won’t be a bit like the Army. He’ll find it very frustrating,” according to author Richard E. Neustadt. As it happens, poor Ike turned out to be a pretty good president. Harry shouldn’t have given him so much hell. But Truman was right—in the main. Politics is different from other businesses, including the military. Many people discover that lesson the hard way.

Others are looking for a hobby. As one Twitter follower told me, rich people go into politics “for the same reasons they buy sports franchises or rocket rides.” It also seems observably true that politics and entertainment have merged and that getting elected is a way to achieve some modicum of fame for people who can’t sing, dance, or make a three-point shot. Ultimately, it may be Bruce Springsteen who explained this theory best: “Poor man wanna be rich / Rich man wanna be king / And a king ain’t satisfied / ’Til he rules everything.” Whether or not The Boss got it right, rich people do constitute a disproportionate share of the candidates vying for public office, especially when compared with working stiffs.

Excerpted from Filthy Rich Politicians by Matt Lewis. (Copyright 2023) Used with permission from Center Street, a division of Hachette Book Group, Inc.