It had nothing to do with business
By 
It appears that Deadspin has effectively been killed, whether it ultimately happens by shuttering the site or having it carry on as the Zombie quarter-assed Barstool imitator G/O tried to order the editors to turn it into. One crucial point here is that Deadspin’s model was financially successful:
Less than a year ago, posts on The Concourse, the section of Deadspin reserved for non-sports coverage, averaged more than twice as many page views as average Deadspin posts, according to internal numbers seen by The Times. Concourse posts made up approximately one of every 50 Deadspin posts.
The top 15 posts, by traffic, on Deadspin 2012-2017 with the posts about sports removed pic.twitter.com/BTtOU8I8UU— Timothy Burke (@bubbaprog) October 28, 2019
Telling Deadspin to “stick to sports” reflects a total misunderstanding of what the site is. Drew Magary’s extremely popular Thursday NFL posts, for example, range widely into non-sports topics, which is one reason they’re so good. There’s no business rationale for wanting to stop it from doing what made it successful. But as Megan Greenwell observes in the essential farewell she filed after her resignation, this is about about a bunch of rich but (justifiably) insecure know-nothings asserting their authoritah, more concerned with implementing petty, arbitrary rules and forcing inane theories down the throats of their professional staff than making money:
There is a version of the story of this company in which idealistic journalists, unconcerned with profit, are posed against ruthless business-doers, concerned about profit above all else. That would be a convenient story, pitching me and my colleagues and friends as people who just care too much about The Truth to yield before the gale-force winds of Capitalism, but it wouldn’t be a true one.
The real and less romantic story is this: The journalists at Deadspin and its sister sites, like most journalists I know, are eager to do work that makes money; we are even willing to compromise for it, knowing that our jobs and futures rest on it. An ever-growing number of media owners, meanwhile, are so exceedingly unwilling to reckon with the particulars of their own business that they refuse to accept our eagerness to help them make money. They’re speaking a language no one else does, proud of their own inability not just to not fail, but to not understand the terms on which they’re failing. The tragedy of digital media isn’t that it’s run by ruthless, profiteering guys in ill-fitting suits; it’s that the people posing as the experts know less about how to make money than their employees, to whom they won’t listen.
[…]
A metastasizing swath of media is controlled by private-equity vultures and capricious billionaires and other people who genuinely believe that they are rich because they are smart and that they are smart because they are rich, and that anyone less rich is by definition less smart. They know what they know, and they don’t need to know anything else.
Since Great Hill Partners bought this company in April, the CEO and his newly hired C-suite have gone to great lengths to show they are the adults here, and that the employees of this company who preceded them are children in desperate need of parenting. They have attempted to institute a dress code and rules about the hours during which employees must be sitting at their desks. They have attempted to intimidate reporters out of reporting true stories about the dysfunction they have created. They have told experienced product managers that quality-assurance testing and other widely accepted best practices are unnecessary because their years of experience are better substitutes. They have driven out several senior managers—most of them women, myself included—by undermining us and condescending to us at every turn.
There is, needless to say, far too much greed and venality in American life. But like the contemporary Republican party, many of our venture capital pirate overlords are so bad that if they operated out of pure greed and venality it would actually be an improvement.