The friendship between President Trump and Fox News star Bill O'Reilly goes way back.

It came to the forefront again this week when Trump offered support for O’Reilly after a news report that the Fox star had paid $13 million to five different women who had accused him of sexual harassment or inappropriate conduct.

“I think he’s a person I know well — he is a good person,” Trump told The New York Times in an interview.

“I think he shouldn’t have settled; personally I think he shouldn’t have settled,” the president continued. “Because you should have taken it all the way. I don’t think Bill did anything wrong.”

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The settlements have turned into a full-fledged crisis for O’Reilly and Fox News, which saw its longtime chairman Roger Ailes leave the network last year under a cloud of sexual harassment claims.

The alleged payouts have prompted more than 60 advertisers to pull spots from “The O’Reilly Factor.” Fox News indicated this week that ads have been moved to other programs on the network.

Trump’s defense of O’Reilly was surprising given the nature of the story, and a transcript of The New York Times interview shows that one of Trump’s aides quickly sought to get the interview back to the subject of infrastructure.

Yet it also highlighted a long friendship between two men who share similar backgrounds and appeared to enjoy each other’s company.

The friendship started in 1990 when Trump, 70, was a flamboyant, socially-ubiquitous real estate developer custom-made for New York's tabloid culture.

O'Reilly, for his part, worked for tabloid news magazine Inside Edition, a nationally-syndicated television program.

“[He was] pretty bombastic then [in 1990], and he’s bombastic now,” O'Reilly, 67, told the Hollywood Reporter in July of 2016.

“Smart guy, very aggressive.”

The two men come from the post World-War II baby-boom era, with Trump born in 1946 in Queens and O'Reilly in New York City in 1949 before growing up in Levittown, Long Island.

It’s unclear how close the two are.

The native New Yorkers have been seen together in New York City in recent years, but before Trump’s presidential candidacy. They have periodically appeared in seats normally reserved for celebrities at Yankees and Knicks games.

Trump appeared on O'Reilly's program on an almost-weekly basis leading up to the election.

When Trump was involved in a feud with then-Fox News star Megyn Kelly and was threatening to boycott the network, he suddenly showed up on “The O’Reilly Factor.”

O’Reilly and Kelly were in-house rivals before the latter left Fox News for NBC.

O’Reilly did not refrain from criticizing Trump during his White House run.

In one segment back in March of 2016, Trump accused O’Reilly of being overly negative, saying the host would have to ask his psychiatrist why.

Trump's last interview with O'Reilly was on Super Bowl Sunday on Fox-TV in February.

Both men are known for being unfiltered, and for addressing matters without caution or anything resembling a script.

Both probably speak out at times when their aides and advisers wish they would be quiet.

For Trump, the defense of O’Reilly appeared to backfire.

A number of commentators questioned why the president would publicly defend someone who had offered millions in payouts over sexual harassment allegations.

“His defense of Bill O'Reilly is morally bankrupt,” Elise Jordan, a former aide to Sen. Rand Paul Randal (Rand) Howard PaulGOP senator to quarantine after coronavirus exposure The Hill's Morning Report - Sponsored by National Industries for the Blind - Trump seeks to flip 'Rage' narrative; Dems block COVID-19 bill Overnight Health Care: Senate Democrats block GOP relief bill | Democrats reveal Medicaid chief's spending on high-paid consultants | Trump calls question about why he 'lied' about COVID-19 a 'disgrace' MORE (R-Ky.) and frequent MSNBC contributor, said on MSNBC's "Morning Joe" Thursday morning.

“I’m saddened reading your comments,” former Fox Business host Rebecca Diamond said in a Thursday tweet directed Trump. “Truly disappointed and vilified all over again. Such comments tell women they won’t be believed.”

MSNBC's Mika Brzezinski called Trump's remarks defending the Fox News Host “disgusting.”



“The advertisers are speaking and women are speaking and I think it’s going to work out — but the president shouldn’t have done that,” said Brzezinski.