How Rich Candidates Burned Cash on Running for Office

The costly realm of campaign politics has claimed its share of the fortunes of yet another business magnate with aspirations to higher office.

Representative David Trone, Democrat of Maryland who co-owns the largest wine retailer in the country, poured more than $60 million of his personal fortune into his Senate campaign in Maryland, according to campaign finance reports filed to the Federal Election Commission. He lost the Democratic primary this week to Angela Alsobrooks, a county executive whose campaign had spent about a tenth of that amount.

A day after Mr. Trone’s loss, Nicole Shanahan, Robert F. Kennedy Jr.’s running mate and a Silicon Valley investor who recently divorced the Google co-founder Sergey Brin, announced that she was doubling her stake in Mr. Kennedy’s independent presidential campaign. Her donation of another $8 million brings her total contributions to nearly $15 million, despite the fact that no third-party or independent candidate has come close to winning a presidential election in modern U.S. history.

Mr. Kennedy’s campaign is so far only about half as expensive as the costliest self-funded presidential campaign this cycle: Vivek Ramaswamy, the Republican entrepreneur, spent more than $30 million of his own wealth on his failed candidacy, dropping out in January after spending $3,500 per vote won in the Iowa caucuses. Doug Burgum, the governor of North Dakota who sold his software company to Microsoft for $1 billion, didn’t even get that far: He dropped out before a single vote was cast after having spent nearly $14 million on his presidential campaign.

It is a time-honored tradition in U.S. politics: wealthy people burning dizzying sums of money to fuel their political ambitions through long-shot candidacies, or — as in Mr. Trone’s case — campaigns with good odds that simply don’t end up working out.

A self-funded campaign is not always a recipe for disaster. Mr. Trone, for example, was successfully elected to Congress after spending a combined $31.3 million of his fortune to run in two House races. He lost to Jamie Raskin in the 2016 Democratic primary, but he won the 2018 primary to succeed Representative John Delaney, another wealthy Democrat. Jon S. Corzine, a liberal Wall Street executive, spent about $60 million, or $108 million adjusted for inflation, to win a Senate seat in New Jersey in 2000.

Here are some of the biggest money-pit campaigns:

Michael R. Bloomberg, 2020 Presidential Campaign

Personal wealth contributed: $1 billion

Dollars per vote: $426.76

It was, by far, the most expensive campaign flop in American history.

Michael Bloomberg, the founder of the financial and media giant Bloomberg L.P. and one of the biggest donors to the Democratic Party, had previously made headlines and history for spending eye-popping sums on his political ambitions. He poured hundreds of millions of dollars from his personal fortune to run for mayor of New York and to stay in office from 2002 to 2013.

But the most expensive race of his career — and also just the most expensive presidential primary campaign ever in U.S. history — stood out not just for the size of Mr. Bloomberg’s war chest but also for how the campaign went down in spectacular defeat. The former mayor dropped out roughly 100 days after getting into the race.

Tom Steyer, 2020 Presidential Campaign

Personal wealth contributed: $341 million

Dollars per vote: $1,320.37

In any other race, in any other year, Tom Steyer’s 2020 presidential campaign would have been a record-breaking flop. Spending $341 million of his hedge fund fortune, Mr. Steyer ultimately earned 258,848 votes, the steepest ratio of money-to-votes of any presidential candidate in U.S. history, and he won no delegates before dropping out of the race.

The yawning hole that Mr. Steyer’s presidential ambitions left in his wallet is eclipsed only by that of Mr. Bloomberg, who spent roughly three times as much and who made a much bigger splash when he jumped late into the Democratic primaries.

Linda E. McMahon, 2010 and 2012 Senate Campaigns

Personal wealth contributed: $98.8 million combined

Dollars per vote: $85.95

Linda McMahon, the former chief executive of World Wrestling Entertainment, spent nearly $100 million to self-fund two Senate campaigns in Connecticut. She decisively claimed the Republican nomination with her enormous cash advantage but ultimately lost both races by wide margins in 2010 and 2012. It was, at the time, the most anyone had ever spent of their own fortune to run for federal office.

Ms. McMahon later donated extensively to Donald J. Trump’s 2016 campaign, and then she joined his cabinet as the head of the Small Business Administration. Her campaign’s senior consultant in 2012, Chris LaCivita, is now one of the top officials for Mr. Trump’s 2024 presidential campaign.

Steve Forbes, 1996 & 2000 Presidential Campaigns

Personal wealth contributed: $74 million combined

Steve Forbes, then the chairman and editor in chief of Forbes magazine, ran two presidential campaigns as a Republican, each time spending about $37 million of his personal fortune in his bid to win the nomination — for a total of $74 million, or $139 million when adjusted for inflation.

The wealthy publisher ran on a platform of abolishing tax brackets and enacting a simple flat tax rate — an idea that later caught on with other Republican presidential hopefuls. Mr. Forbes won a few state primaries in 1996, placed second against George W. Bush in the Iowa caucuses in 2000 but ultimately fell short in both campaigns.

Ross Perot, 1992 Presidential Campaign

Personal wealth contributed: $65 million