Seven Big Spenders Who Emptied Their Wallets and Still Didn’t Win

Polls suggest Democrat Beto O’Rourke’s tens of millions of dollars will go to waste next week in his bid to unseat Sen. Ted Cruz (R-Texas).

If O’Rourke (pictured above center) does lose to Cruz, it will be one of the most spectacularly unsuccessful campaigns — measured by dollars spent — in American history. O’Rourke, currently a U.S. representative from El Paso, raised $38 million from July through September; that’s the highest quarterly total for any Senate candidate in history.

For the entire campaign, O’Rourke has hauled in nearly $60.8 million, compared with just shy of $35 million for Cruz. That puts Cruz in an unusual spot for an incumbent — not only does he trail in fundraising, but he also trails by a substantial margin.

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Despite the avalanche of cash pouring into O’Rourke’s campaign, Cruz has maintained a steady lead in the polls.

He has not lagged in a single public survey and enjoys a lead in the RealClearPolitics average of 6.8 percentage points.

If the polls are right, O’Rourke will lose. But he won’t be alone. Despite conventional wisdom that the size of a candidate’s wallet dictates victory or defeat, plenty of well-funded candidates have lost their races.

Here are seven.

1.) Hillary Clinton, 2016 presidential race. The Democratic nominee for president spent $563.8 million in the most expensive presidential campaign in history. She outspent President Donald Trump by a three-to-two margin. Add in money spent by outside groups, and Team Clinton spent roughly two dollars for every one spent by Trump and his allies.

Yet all that dough did not do Clinton a lot of good. It was, by far, the most expensive failure in American politics.

2.) Rick Lazio, 2000 Senate race. The fundraising record that O’Rourke broke had belonged to Lazio, a New York Republican who attempted to win a promotion from U.S. representative to senator.

The race was supposed to be a marquee match-up between Clinton, who at the time was the outgoing first lady, and New York City Mayor Rudolph Giuliani. But because a prostate cancer scare back then prompted Giuliani to drop out of the race, the GOP recruited Lazio as his replacement. Then a congressman from Long Island, Lazio dumped $40.6 million into the race.

Clinton, who only recently at that time had established residency in the Empire State so she could make the run, spent less than $30 million by comparison.

But Lazio (pictured above left) found votes much harder to come by than campaign contributions. He won only 44 percent of the vote.

3.) Michael Huffington, 1994 Senate race. Then a little-known congressman, Huffington tried to use his oil wealth to buy a Senate seat in California. The $28 million he spent is the equivalent of about $69.4 million in today’s dollars. At the time, it was the most expensive Senate race in history.

Sen. Dianne Feinstein (D-Calif.) was running for her first full six-year term after having won a special election two years earlier. She spent the comparatively small sum of $16 million.

Unlike many of the big-spending losers on this list, Huffington did not get blown out. California at the time was far more Republican-leaning than it is today. That, combined with Huffington’s wealth and the exceptionally good electoral year that 1994 was for the GOP, nearly carried Huffington to victory. He came within 1.9 points.

In the end, it was Huffington’s wife, Arianna, who would become famous and influential: She founded Huffington Post. Michael Huffington divorced her and came out as bisexual.

4.) Jon Ossoff, 2017 House race. Shortly after documentary filmmaker Ossoff threw his hat into the ring in a special election to replace former Rep. Tom Price — a Georgia Republican who had resigned to become secretary of the Department of Health and Human Services (HHS) — money started flowing in from liberal activists all over the country.

Democrats were desperate to flip a district where Hillary Clinton had nearly fought Donald Trump to a standstill. That outside money helped make the race the most expensive of any House campaign in history.

Democrat Ossoff spent more than $17.8 million. Republican Karen Handel could manage less than $6.2 million.

But Ossoff’s financial advantage did not translate to victory in the Republican-leaning suburban district outside Atlanta.

5.) Linda McMahon, 2010 Senate race. As the wife of World Wrestling Entertainment (WWE) founder Vince McMahon — and the president and CEO of the company — McMahon had plenty of personal wealth when a Senate seat in her home state of Connecticut came open with the retirement of incumbent Democrat Chris Dodd.

And the Republican candidate spent a total of $50.2 million — compared to just $8.7 million by Democrat Richard Blumenthal, the state’s attorney general.

Connecticut was and remains one of the deepest blue states in the country. McMahon won 43.2 percent of the vote and carried one county.

5a.) Linda McMahon, 2012 Senate race. When incumbent Joe Lieberman decided not to seek re-election, McMahon came back for another shot.

The race followed a familiar pattern. McMahon spent a similar amount of money, $49.5 million, and got a nearly identical share of the vote, 43.3 percent. Democrat Chris Murphy coasted to victory despite spending $10.4 million.

At the outset of his presidency, Trump appointed McMahon to run the Small Business Administration.

6.) Kay Hagan, 2014 Senate race. When Democrat Hagan won her first race for the Senate in 2008, she was the underdog, handily defeating incumbent Republican Elizabeth Dole though she was outspent by more than $11 million.

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When she ran for re-election in 2014, she enjoyed an even bigger financial advantage than Dole had. She spent almost $24.9 million, compared with $10.5 million by GOP challenger Thom Tillis. The race was close, but Tillis squeaked out a victory.

7.) Carly Fiorina, 2010 Senate race. Fiorina’s tenure as CEO of Hewlett-Packard was the source of both her qualifications to be senator and the personal wealth it would take to defeat more experienced candidates.

Fiorina managed to win the primary against former U.S. Rep. Tom Campbell, but the general election was far rougher for her. She spent $21.3 million, compared to just $8.6 million by incumbent Democrat Barbara Boxer.

It didn’t matter. Boxer dispatched her by 10 points.