Some things just never change.

Back in 1990, Hugh Hefner put Donald Trump on the cover of his magazine, a rarity among men.

In the magazine, Trump was speaking in political terms. Even then, he was bashing the system for being in disarray, at least from his point of view.

"I think if this country gets any kinder or gentler, it's literally going to cease to exist."

RELATED - Donald Trump Says This Legendary Actor Ruined 'The Apprentice'

In truth, Trump cooled down in the '90s and he almost became obsolete, losing lots of money while his fame subsided. Trump can thank both the likes of Hugh Hefner, along Mark Burnett for keeping him relevant.

Once 'The Apprentice' aired, Trump's image resurfaced and suddenly, he was making millions again thanks to the show and the various endorsement deals that followed.

It might be hard to believe, but Donald was initially unsure about the gig, claiming that reality TV was viewed as trashy... We guess money talks.

We're not entirely sure where Mark Burnett stands, but we do know that before his passing, Hefner wanted nothing to do with Trump and their former friendship.

Thanks to Hef's son Cooper, we know the exact moment where things went array between the two.

It Started With A Friendship And Presidential Support

The two started off as close friends and in fact, some of the Playmates actually spoke well about meeting Trump at the mansion. Holly Madison was among those that chimed in.

"I met Donald Trump a few times, but I don't know him well or anything. He was always polite and really nice."

"It's kind of surreal seeing Donald Trump run for president because I used to see him at parties sometimes and run into him."

RELATED - This Is Holly Madison's Life After The Playboy Mansion

Back in 2006, the two were still very close, so much so that Donald brought 'The Apprentice' team to Hefner's mansion. Surya Yalamanchili recalls the experience alongside News Week.

"After a fireside chat with Hef, we headed to the backyard, where dozens of women, some wearing bikinis, others sporting bunny ears and bow ties, surprised our team with a pool party," wrote Yalamanchili.

"Toward the end of the evening, I found myself in a small circle, conversing with Trump, Hefner, and another contestant. With a wry smile, Trump looked at Hefner and said, 'It's hard for me to tell which of these girls are yours and which ones are mine.'"

Even during Trump's run, Hefner appeared to be by his side, issuing this statement, "Christian crusade to eliminate all sexual activity that doesn't lead to procreation."

"Instead, voters nominated Donald Trump, a thrice-married New York entrepreneur who once owned the Miss USA pageant, over Cruz, the son of a pastor," Hefner wrote. "It's a sign of the massive changes in the 'family values party' and proof of…a sexual revolution in the Republican Party."

However, it would all change once Donald took over.

Hefner's Son States His Dad's Regret

Suddenly, following Donald's election win, Hefner disappeared from his side. Fans noticed a crucial moment, that included Hefner removing an essay from the Playboy website. It turned into nothing but regret Hefner, especially considering Donald made the magazine cover.

RELATED - Hugh Hefner Ended His Friendship With Donald Trump For This Reason

The friendship was broken and Hef's son Cooper would elaborate on the reasoning via Twitter, with a cluster of tweets.

It seems as though the heart of the problem was contrasting political views, especially when it came to certain touchy topics, like same-sex marriages. Hefner had always been a huge advocate, even before the conversations were taking place.

"Yes, there are lifestyle components to Playboy, but it's really a philosophy about freedom and, right now, as history is repeating itself in real-time, I want Playboy to be central to that conversation," he said.

Despite the harsh words, fans were surprised that Trump never issued a statement back, especially given his constant use of the social media platform, Twitter.

Trump Never Responded

In what was a big surprise, Trump kept things quiet following Hefner's son's statement.

Following the passing of Hefner as well, Donald decided not to issue a statement, it was clear the relationship was broken and beyond repair, despite the close bond they held in the past.

Surely, there was still a respect factor from Trump's side, given all the opportunities provided to him by Hefner over the years, especially when he was down.

It was for the best that Trump kept quiet, now if only he could've used that mindset for a couple of other situations...

NEXT - Donald Trump Dragged Online Over Bizarre Rant About Lebron James