Some did it out of altruism. Some believe there's still money to be made in the newspaper business. But some saw newspapers as a vehicle to drive their own agendas.
But after years of rising news print costs, declining circulations, and whacks to newsroom staff, one thing is now undeniably true: Newspapers are cheap.
In 2013, Jeff Bezos - the CEO of Amazon.com - paid $250 million for The Washington Post, instead of the billions it was once worth. The same year, John Henry - the owner of the Boston Red Sox - paid $70 million for The Boston Globe, compared to the $1.1 billion The New York Times paid for it in 1993. And in 2013, Warren Buffett went on a newspaper buying spree, and picked up about 30 community newspapers. He now owns 54 daily papers. Buffett has said in multiple interviews that he believes in community journalism and the value it provides.
"If it wasn't clear that newspapers have become trophies for the wealthy with an interest in journalism or power - or a combination of both - it should be now," Andrew Ross Sorkin wrote for The New York Times in 2013 while describing the paper-buying scene.
The upside of billionaire owners is they can be patient with profits and losses. Bezos wrote in a 2013 memo to Washington Post staff that he had no intention of changing the newsroom values of the paper.
"I won't be leading The Washington Post day to day. I am happily living in the 'other Washington' where I have a day job that I love," Bezos wrote to the Post newsroom.
Ken Doctor, a news industry analyst and author of Newsonomics, pointed out to me that recent billionaire newspaper owners have more often than not invested in their papers, rather than making budget cuts to turn a profit. Bezos, he said, is the most astounding example of all, because he reinvested the most.
"You look at how The Washington Post has assumed a new national importance in Trump times, and his addition of staff there has been dramatic," Doctor said.
Doctor further noted that John Henry and The Boston Globe - along with Mankato billionaire Glen Taylor, who bought The Minneapolis Star Tribune for $100 million in 2014 - are two more examples of billionaires being good for newspapers.
"Each of them has bought into the industry within the last two years now, and in general, they are along the better owners," Doctor said. "They also, to a varying degree, have a civic interest. They believe in the value of newspapers for communities. So you put those two things together, and what each of them has done has essentially stabilized their operations."
But when pressed on whether the sudden influx of wealthy owners is always a good thing for newspapers and their staffers, Doctor said the bottom line is really that "It depends on which billionaire you get."
A pair of cautionary tales are billionaire casino mogul Sheldon Adelson and multimillionaire developer Doug Manchester.
Adelson, who is worth approximately $32 billion (several times Anschutz's net worth), purchased The Las Vegas Review-Journal in 2015 for $140 million. And immediately after the purchase, disturbing reports of Adelson's new influence began to leak out of the newsroom.
Two days after Adelson's lawyers lost their attempt to have a judge removed from a contentious lawsuit that threatened Adelson's gambling empire, Review-Journal staffers were summoned to a meeting with the publisher and told they must monitor the courtroom actions of the judges and two others in the city. When the reporters protested, they were told it was an instruction from above and that there was no choice.
Doug Manchester bought The San Diego Union-Tribune in 2011 for an undisclosed sum (though some reports had the purchase amount as high as $110 million), and then sold it for $85 million in 2015 to the Tribune Publishing Company.
But while he owned it, Manchester turned the paper extremely political. A conservative Republican with a distinctly pro-business agenda, Manchester blurred the normal editorial-opinion lines with the Union-Tribune to further his own interests during his tenure as owner, many critics said.
Doctor said from what he heard out of San Diego, the newsroom head was "good at keeping (Manchester) at bay, but it raised a lot of suspicions about the kind of news coverage you would get out of (the Union-Tribune)" because Manchester was "plainly using it for political ends."
In 2012, when Boston investment group 2100 Trust - which briefly owned The Colorado Springs Gazette - bought The Orange County Register and six other daily papers, The Los Angeles Times reported that some Register employees were "relieved that the paper did not go to Manchester."
"Newspapers have gone from the public markets to the hands of a relatively few billionaires who have an appetite for social, civic and financial roles," Doctor said in another 2013 New York Times article.
Anschutz, however, never publicly laid out his vision or motive for The Colorado Springs Gazette. He never called a newsroom meeting. I never met him or spoke to him, and it was the same for most of my colleagues while I was still at The Gazette.
And while he may be media-shy, he's definitely not politically shy. He's been bankrolling conservative causes and organizations for years, trying to shape public opinion, in ways that echo moves by Adelson and Manchester.
Just after Anschutz bought The Gazette, Media Matters raised questions about whether he would mold the paper's content the same way that he'd done previously with The Oklahoman, which he had acquired in 2011, about 14 months before buying The Gazette. (Personally, I think that question has been answered, but maybe it's more of an ongoing tug-of-war with Gazette journalists on one side and Anschutz, McKibben and Steever on the other. Makes me wonder what the atmosphere is these days in The Gazette newsroom.)
Doctor says he doesn't expect to see billionaires racing to buy up more newspapers, but the important thing for Colorado news consumers is that it's not out of the realm of possibility that Anchutz may still snatch up The Denver Post.
Last November, Gazette Editor Vince Bzdek said during a speech at Colorado College that Anschutz had tried to buy the Post but that the paper's owners wouldn't sell, The Colorado Independent reported.
"If they would sell he would buy it tomorrow," Bzdek said. And that was just seven months ago.
From my understanding, the likely scenario was that Digital First Media, the Post's parent company, balked at only selling The Post, as opposed to its entire media empire altogether for a lump sum. That would have driven the price up significantly, and included 13 other papers in Colorado. From what I've heard, Anschutz is only interested in The Denver Post. So the deal fell through.
It's also worth noting here (and because he never responded to my interview requests) that in the same speech, Bzdek said he had been "trying to find out 'Is (The Gazette) going to be a mouthpiece for this guy? Is this something he's going to use to drive his agenda?' I've not found that to be the case. I found he has this ... commitment to the betterment of Colorado Springs."
Well, I certainly hope so. But I know a few more people who could probably use convincing.
Either way, unless there's another billionaire or would-be newspaper owner waiting in the wings to spring up out of nowhere and rescue the cash-strapped Denver Post, it seems like Anschutz could still wind up with it, Doctor said.
"The logical alternative is that there's some other person or small group that has $50 to $100 million," Doctor said, throwing out a range of what the Post could sell for. "Because we're talking about the future of the daily press in Colorado. It's still very, very powerful, and given the politics of the country, it's a purple state. If you control the daily press, even though it is weakening, throughout the state, from Boulder to Colorado Springs to Denver ... that's political power.
"That's what's at stake here."
The price of The Denver Post, however, could be even lower. This is pure speculation, since a deal would be contingent on how badly Digital First Media's primary hedge fund owner Alden Global Capital wants to unload it and how much someone like Anschutz would be willing to pay, but I've spoken to several newspaper veterans who have suggested The Post could go for even less than the range Doctor suggested, based in large part on the state of the industry and its continually declining revenues.
The other rumor that's making the rounds these days is that Alden Global Capital may actually now be willing to break off The Post from the rest of its media empire and sell it as an individual asset to Anschutz. One source of mine even told me the rumor is the company is actively pursuing Anschutz as a buyer. And, as Bzdek confirmed in November, it's common knowledge that Anschutz wants Colorado's flagship daily newspaper.
And what will happen if Anschutz does buy the Post?
Some of the people I spoke to believe he'll immediately break the Denver Newspaper Guild's hold on the Post newsroom, and then lay off a lot of overlapping reporters (why would he need two sports desks that both cover the Denver Broncos, for instance?) Others suggested he'd immediately do away with The Cannabist, a spin-off business The Post began after Colorado legalized marijuana in 2012, because Anschutz is solidly anti-marijuana.
But the more pervasive fear, and the one that I hold, was articulated by former Colorado Springs City Councilwoman Jan Martin.
"I have no reason to believe that he wouldn't, because of the experience here in Colorado Springs," Martin said, when I asked her if she thought Anschutz would use his influence as owner to alter the news coverage by The Denver Post after buying it.
"And it's so sad, because the average reader isn't going to even notice, because it's so subtle," Martin pointed out. "It could be something as simple as headlines on Associated Press stories. But the headline drives the story. So it's a real concern to me. It's one thing to live in Colorado Springs and know we're a conservative city and have that be our voice; it's a whole other thing when it moves to Denver. That's millions of people, not just half a million."
What happens when a billionaire with the resources of the largest daily newspaper in the state has control over how it covers city and state politics? Over issues like taxes, the environment, education? Energy regulation, tourism, even zoning for business deals like the Aurora Gaylord Hotel project that his underlings were so hellbent on smearing?
As both Doctor and former Gazette editor Jeff Thomas reminded me, such activism is really nothing new in the news business.
"Find me a city in America where a publisher hasn't tried to use their newspaper to sabotage someone else's competing interest or boost their own," Thomas said. "None of which is to excuse it, but ... I don't regard Phil Anschutz as anything terribly singular, other than the amount of cash he has at his disposal. Nor do I necessarily believe his intentions are nefarious. He may genuinely believe that a 'healthy Colorado Springs is good for everybody,' and that's classic publisher thinking too."
As Doctor further noted, "It's not a new issue. You go back to when most of these papers were community-owned, and they were owned by wealthy people, usually people with other interests. That's a whole can of worms right there."
But just because corruption in the news business isn't new doesn't mean it should be tolerated.
Still, Doctor concluded that there's less of a trend of media companies - both print and broadcast - being bought up by the wealthy as opposed to consolidation throughout the industry. And that could be accelerated this year, he said, by potential changes to federal rules that govern media company ownership.
"I think it is proper to fear it and be concerned by it," Doctor concluded when pressed on whether he's worried by figures such as Adelson, Manchester and Anschutz and their involvements in the newspaper business. "But it's not a major trend right now. I think the major thing to watch in 2017 ... is that the FCC under Trump may rewrite cross-ownership rules."
If owners like Anschutz start buying up TV stations as well as outlets like The Denver Post and The Colorado Springs Gazette after a rewrite of federal regulations under Trump, that could spawn an entirely new era of corporate interests blurring the lines of what's trustworthy in the news and what's not, especially in this age of "fake news" and a commander-in-chief who believes the press is the "enemy of the people."