America's press is dead. Long live the billionaires.

Is a billionaire interviewer really the last line of defence against Donald Trump?

CNN anchor John King on Donald Trump: 'We got played, again.' (Photo from Crown Arena, Tuesday, Aug. 9, 2016 by AP photographer Evan Vucci)

Donald Trump at Crown Arena, Tuesday, Aug. 9, 2016, in Fayetteville, N.C. (Evan Vucci, AP)

Friday felt familiar.

Four years ago, in the fall of 2012, billionaire real estate mogul, TV star, and gold-plating aficionado Donald Trump teased the media with the suggestion that he had a big announcement to make. He called it a “bombshell.” He called it an “October surprise.” When it finally happened—on Oct. 24 of that year—it turned out to be a YouTube video. Facing a camera sitting at desk-level, Trump offered to send $5 million to a charity of Barack Obama’s choice if the President released his passport and college admission records.

Trump’s challenge came a year after Obama had already released his full birth certificate, and about four years after the “birthers” movement—a collection of people who believe Obama was born outside the United States (possibly Kenya), and to whose theories Trump fully subscribed—started gaining traction, demanding proof the President was an American.

But in October 2012, when he made his demand for Obama’s passport and college information, Trump remained unconvinced. About a month before he challenged Obama, Trump tweeted: “Wake Up America! See article: ‘Israeli Science: Obama Birth Certificate is a Fake.’” The article to which Trump linked appeared on a site called Freedom Outpost, which more recently falsely told its readers that “homeland security is taking control of the electoral process,” and that Obama will “suspend” the election if Democratic nominee Hillary Clinton is “too sick.”

The question of whether Trump, now the Republican nominee for president, still, in 2016, believed the claims of that so-called “Israeli science” from 2012, felt like it would go unanswered—that is, until Trump’s campaign convinced TV networks everywhere Friday that Trump had something new to say. “I am now going to the brand new Trump International, Hotel D.C. for a major statement,” Trump tweeted Friday morning.

The resulting announcement was as much of a trolling exercise as the 2012 video. As the TV cameras remained locked on the dais, fearful of missing a split second, a number of veterans—including well-known birther, retired Air Force Lt. Gen. Thomas McInerney—approached the microphone to praise Trump and his campaign, using the TV attention as more free advertising time. When Trump did finally appear, his statement was brief, provocative, and removed from reality. First, he laid the blame for the birther movement’s roots erroneously with Hillary Clinton. Then he declared that he, Trump, had put an end to the issue by demanding Obama release his birth certificate (“I finished it. You know what I mean.”). Finally, Trump said: “President Obama was born in the United States.”

“We got played, again, by the Trump campaign. Which is what they do,” John King said on CNN moments after it was all over. Few could argue with that.

Enter Mark Cuban.

Mark Cuban is a billionaire. He is an investor and owner of the Dallas Mavericks basketball team, America’s largest chain of movie theatres, and a film production company. He also appears on TV; he is one of the sharks on investment reality show Shark Tank. And Mark Cuban dislikes Donald Trump.

On Friday, as the news media realized it had been played by Trump’s birther announcement, Cuban took to Twitter. Much like Trump did four years ago, Cuban issued a challenge. He offered Trump $10 million “to the charity of YOUR choice if you let ME interview you for 4 hrs on YOUR policies and their substance.” He stipulated some rules that needed to be followed, including that Trump was not allowed to mention the Clintons “or discuss anything other than the details and facts of yr plans,” and that nobody other than Cuban, Trump and a film crew would be allowed in the room for the duration of the interview.

Trump did not respond.

Entrepreneur Peter Thiel speaks during the final day of the Republican National Convention in Cleveland, Thursday, July 21, 2016. (AP Photo/Mark J. Terrill)

Entrepreneur Peter Thiel speaks during the final day of the Republican National Convention in Cleveland, Thursday, July 21, 2016. (AP Photo/Mark J. Terrill)

American media have had a tough relationship with billionaires lately.

Gawker, the tabloid website, shut down in August after a long legal battle with Terry Bollea, a.k.a. former pro wrestler Hulk Hogan. The same month Trump posted his YouTube challenge to Obama in 2012, Gawker published an explicit video of Bollea, which the wrestler immediately requested be removed from the site. Gawker’s founder, Nick Denton, refused, citing protections of a free press in the First Amendment. But Bollea pressed the issue, and sued Gawker for $100 million. In January, Gawker sold a minority stake to a Russian oligarch, billionaire Viktor Vekselberg, to bring in money to fight the case. But it didn’t matter. In March, Bollea was awarded $140 million in damages—a price Gawker was, ultimately, unable to pay and thus powerless to challenge.

But before Gawker closed up shop forever, it emerged that a Silicon Valley billionaire, Peter Thiel, had quietly bankrolled Bollea’s case against the website—contributing $10 million in funding. Thiel had a long-standing gripe with a Gawker-owned site, Valleywag, which had outed him back in 2007.

The reveal that Thiel was funding Bollea’s fight against Gawker came only a few months after Trump told a crowd that, were he to become president, he would “open up” America’s libel laws to make it easier to sue news organizations. “When they write purposely negative and horrible and false articles, we can sue them and win lots of money,” he promised. Trump’s verbal attacks on media outlets are well documented. He has for years railed against critical coverage he deems unfair, and regularly tries to belittle TV news shows over their ratings, and newspapers or magazines over their readership. Outlets covering his campaign are regularly banned from his events.

In July, Thiel spoke at the Republican convention, publicly endorsing Trump’s plan for America. But the endorsement cut both ways; there is little question Trump likes Thiel. Just a month earlier, Thiel’s lawyer sent Gawker a letter demanding that the site reveal its sources for a story that suggested Trump’s hair is a $60,000 weave.

In Gawker’s final post—interpreted as its obituary—Denton remembered the feeling the Internet once provided: an “island off the mainland, where people could be themselves.” That freedom, he wrote, was illusionary. “The power structure remains,” Denton wrote. “There are just some new people at the apex, prime among them the techlords flush with monopoly profits.” Referring to a category the site frequently snidely used when it highlighted those power structures in America–“how things work”–Denton wrote that “Gawker’s demise turns out to be the ultimate Gawker story. It shows how things work.” In other words, the checks on power that America has enshrined in its foundational document were rendered impotent when faced with a wall of cash. For all the truth you might have, in America, money is the truest calling card of credibility.

Which brings us back to Mark Cuban.

There is something thrilling about his challenge. The reaction certainly suggests so, anyway. Cuban’s first tweet to Trump had been retweeted more than 33,000 times by the end of Friday, and liked by 48,000 users. The subsequent tweets, those highlighting the rules, were reposted thousands of times. News sites everywhere jumped on it, of course, and amplified it even more.

Mark Cuban is not a journalist. And any journalist offering a similar deal—even if they were able to bankroll it independently or crowd-fund it–would never be taken seriously. Quite the opposite, probably: they would be ridiculed, most harshly by their peers. Yet, the striking thing about Cuban’s challenge, and perhaps what made it so popular, is that beyond the appeal of its spectacle, it sounds like a good idea. It tugs at a nagging, sad feeling amongst those who believe Trump should be forced to answer serious questions seriously: that having a willing billionaire as the questioner might now be the only way to get it done.

We feel this way because Cuban versus Trump seems like a fair fight. And because we have learned by cultural osmosis that the only way to beat the player is to be a player. And because we think smart investing matters more than smart reporting. And because for all the supposed power and reach and research and platform of a free press, we know that money can easily buy all of that—or silence it.

Because we know how things really work.

Looking for more?

Get the Best of Maclean's sent straight to your inbox. Sign up for news, commentary and analysis.