Jeffrey Epstein aggressively targeted billionaire Leon Black with a slew of demanding emails, urging him to provide millions annually to sustain Epstein’s extravagant lifestyle.

The disgraced financier, known for his conviction as a sex offender, cautioned Black that his financial advisors and “retarded” children had caused a “really dangerous mess” by trying to halt the financial flow, as revealed in emails obtained by the New York Times.

“I never want to have any more uncomfortable money moments with you, I find it very distasteful,” Epstein expressed in a November 2, 2015, email to the founder of Apollo Global Management.

“So to be clear, my terms are as follows. I will only work for the usual 40 million per year. It needs to be paid, 25 million upon signing an agreement, 5 million every 2 months thereafter for 6 months i.e., March, May, June. This can begin if I am able in January. I will immediately stop work if the payment is not received,” he detailed, according to the report.

The emails exchanged between Black and Epstein in 2015 and 2016 highlight the deep ties between the two, who were not only business partners but also close friends.

Black, 74, employed Epstein as his wealth management advisor, who offered guidance on everything from taxes to the billionaire’s world-art collection.

For his services, Epstein was paid by Black to the tune of more than $150 million over the years, even after he was busted in 2004 for molesting a teenage girl, an offense that put him on the sex offender registry.

Black quickly became Epstein’s primary source of income, but by 2016 it was clear that the billionaire was reluctant to keep the money flowing, according to the Times.

That’s when Epstein threw a tantrum across dozens of emails that he fired off through his personal assistant in a battle that lasted several months, the outlet reported.

In one, Epstein called Black’s other financial advisors a “waste of money and space.”

In another, he claimed the team had created “a really dangerous mess.”

Epstein even railed on Black’s children, who he called “retarded” for supposedly making a mess of his estate.

Epstein eventually offered a concession after months of relentless money-grabbing, telling Black: “Of course re any non financial issues, I am always there for you and will continue to be the best friend I can be.”

The Times did not view any return emails written by Black, but the pressure campaign appeared to work.

Black continued to feed millions in fees and loans to Epstein for the never several years until the perverted financier was arrested up in 2019 for his decades-long sex trafficking schemes.

Black was pushed out of Apollo in 2021 for his ties to Epstein — which date back as far as 1990.

The Wall Street genius denied any knowledge of Epstein’s illicit behavior, but was accused of dipping his toe into the debauched world.

One woman sued Black for allegedly raping her in Epstein’s Manhattan townhouse, a case she eventually dropped.

Another former girlfriend filed a lawsuit claiming the billionaire sexually assaulted her — and Black turned to his wealth manager for advice about paying her millions of dollars to keep it quiet, according to court records and one of the many emails obtained by The Times.

That suit was dismissed by a judge who ruled the woman could not pursue the case after she received $9.5 million from Black as part of a nondisclosure agreement that followed their six-year relationship. 

Black also allegedly wired hundreds of thousands of dollars to at least three women who were associated with Mr. Epstein for unknown reasons.

Susan Estrich, a lawyer for Black, asserted that all payments from Black to Epstein were purely for legitimate tax- and estate-planning services, as proven by an outside law firm hired by Apollo to review the pair’s relationship.

“After an exhaustive investigation more than four years ago, the Dechert law firm concluded that Mr. Black paid Epstein only for tax and estate planning advice that saved him and his family billions of dollars. To imply that Epstein somehow had influence over Mr. Black is false and patently absurd. Indeed, it was Mr. Black who fired Epstein because he was disruptive and believed the fees for his services were excessive,” Estrich said in a statement to The Post.

“The Dechert Report also found that Mr. Black had no knowledge of Epstein’s criminal activities. Mr. Black has never abused a woman in his life and any such suggestion is false.”

Whit Clay, a spokesman for Black, emphasized the billionaire “very much regrets” ever making payments to Epstein.