Over his 15-year career, the artist and creative director Ryder Ripps has built websites for the likes of Kanye West, who is now known as Ye, and Kenzo, designed album covers for musicians such as Grimes and Pop Smoke, and shown his work in respected New York galleries. But across mediums, what he does never entirely changes. He finds things online and repurposes them.

It’s gotten him in hot water before but never sued, until recently.

Last spring, Mr. Ripps created a series of non-fungible tokens (NFTs) that looked exactly like Bored Apes — the digital tokens that were hyped in 2021 and 2022 by celebrities including Gwyneth Paltrow and Stephen Curry. Then he named them after himself and sold them. It was the culmination of a monthslong campaign raising awareness about what he says is ripped-from-4chan offensive imagery in the Bored Apes, as well as the artistic vacancy in the speculative world of NFTs.

“It’s not just corny,” Mr. Ripps said of the Bored Apes. “It’s morally wrong.”

Whether Mr. Ripps had committed an act of creative reuse or the theft of intellectual property is, like so much contemporary art, a matter of interpretation.

Mr. Ripps, whose career reached a surreal apex in 2018, when he worked as Ye’s creative factotum, has a reputation as an inveterate self-promoter and shameless appropriator who channels the absurd currents and nasty impulses of digital culture. He has covered a model of the Twin Towers in images of memes and celebrities, sold an NFT featuring an audio file of him and the rapper Azealia Banks having sex, and fabricated an 18-karat gold medallion of Pepe, the cartoon frog that was adopted as an internet hate symbol.

He has not, in other words, gained oodles of trust. Some of his design contemporaries dismiss him out of hand. To them, Mr. Ripps’ Bored Ape project looks like a bid to thrust himself back into the zeitgeist, several years after his intense but fleeting professional relationship with Ye brought his work into the Oval Office, then left him out in the cold. (Last fall, Mr. Ripps also spoke out publicly against Ye’s antisemitic tirades.)

But the creators of the Bored Apes are taking him very seriously: In June, Yuga Labs, the parent company of the Bored Ape project, sued him in federal court for violating its trademarks. Mr. Ripps says that his NFTs are satire and that Yuga Labs — which is the target of a class-action lawsuit accusing the company of artificially inflating the value of the NFTs through celebrity endorsements — is stifling his creative expression.

(A spokeswoman for Yuga Labs said: “We are focused on continuing to innovate and lead in the web3 space, not on the malicious lies and fallacies of an insatiable internet scammer seeking fame and fortune.”)

The NFT boom is over, and the cryptocurrencies that pay for them have crashed. But the closely watched case goes to the heart of pressing new questions about digital ownership.

And it has forced one of the defining internet artists of the 2010s into conflict with a culture he helped shape, one in which the boundaries among trolling, art and commerce are irrelevant. For Mr. Ripps, it isn’t just that the Apes look offensive, it is offensive that the Apes are coming to stand in for all internet art.

According to Mr. Ripps, the Bored Apes have no point beyond grabbing attention and making money, no authentic critical perspective. It’s a criticism others have made about him.

Where Downtown Meets the Internet

Mr. Ripps lives in an old mining town about an hour north of Los Angeles but grew up mostly in New York City. (His parents, the artist Rodney Ripps and the designer Helene Verin, were each painted by Andy Warhol.) In 2009, after finishing a degree in media studies from the New School, Mr. Ripps created Dump.fm, an influential image-based chat platform that recalled the 1990s internet on which he was raised. It established him in a niche but influential community of young, digitally native artists and designers who liked to hang out where downtown met the internet.

VFiles, a web community and cooler-than-thou boutique that Mr. Ripps helped build, was one such place. There, once-fringe young designers like Hood by Air’s Shayne Oliver and Virgil Abloh were discovered by big brands and celebrities.

Patrik Sandberg, a writer and editor who helped create VFiles, credited Mr. Ripps for pioneering the “self-aware internet look,” a kind of retro anti-design that can be seen everywhere now, including places like the cult clothing line Online Ceramics and the website of the cannabis-infused seltzer Loki. But Mr. Ripps quickly left VFiles in 2012 amid a feud with the site’s owner.

“He has a history of burning bridges with every person he ever works with,” Mr. Sandberg said of Mr. Ripps.

(“I don’t agree with the characterization that I’m mean,” Mr. Ripps said in response. “I just want to be heard. I have strong points of view, that’s for sure.”)

Mr. Ripps started his own agency, OKFocus (where one of his early clients was Mr. Abloh’s streetwear brand, Been Trill) and began to try his hand publicly at conceptual art, efforts that would set his reputation in the art world as a chauvinist and a troll.

Mr. Ripps’s first solo show, “Ho,” a collection of large oil paintings of distorted images of the fitness influencer Adrianne Ho, earned condemnation from the feminist website Jezebel. In a 2014 project called “Art Whore, Mr. Ripps paid two sex workers to draw with him as part of a one-night residency at the Ace Hotel. (“This work questions the economics of art, the dynamics of gender and the role of the internet in the production of art,” he wrote at the time.) Rhizome, an influential New York digital art and culture group that had celebrated Dump.fm, denounced the piece as “unthinking, unethical and dull.”

“I was really hurt,” said Mr. Ripps, who expected — and perhaps wanted — a negative reaction from digital media and feminist writers but was surprised that the downtown art community had responded similarly.

The backlash mostly cleaved Mr. Ripps from the gallery world, though Magda Sawon, his gallerist, said she planned to restage “Ho” in Los Angeles this fall. “It was capturing this very early moment of influencers establishing their territory and how protective and corrupt those people are,” she said.

But he had already become an in-demand designer for large brands looking to borrow a little of that downtown edge. From 2013 to 2017 Mr. Ripps designed the branding for Soylent, the meal replacement start-up; made ads for Gucci and Marc Jacobs; and helped produce two songs for Miley Cyrus.

One day in 2014, Mr. Ripps got a call from Ye. He had been looking at the Been Trill website, he said, and he wanted to meet the next day.

The Ye Era

If Mr. Ripps had been surfing the tides of creative success, this was a chance to touch the moon. Ye’s centrality to culture had long been obvious to Mr. Ripps, who in 2012 created a website that falsely claimed to be the first public project of Donda, Ye’s creative agency.

Ye had a habit of plucking (and sometimes quickly discarding) young and buzzy talent to work for him, including Mr. Abloh, Jerry Lorenzo of Fear of God, and Matthew Williams, now the creative director of Givenchy, as well as scores of lesser-known figures, like the former Yeezy general manager Laurence Chandler.

Shortly after Mr. Ripps sat down in Ye’s living room, he said, Ye surprised him by turning around an open laptop, which Mr. Ripps said was playing hard-core pornography. He asked Mr. Ripps to explain its significance.

Mr. Ripps improvised an answer about the interplay of art and sex, which seemed to satisfy Ye. Ye then began playing — and then rapping over — a series of demos, a performance that went on for half an hour, Mr. Ripps said. When he was done, Ye sat down and asked to see Mr. Ripps’s prepared ideas.

After that first meeting, Ye and Mr. Ripps would speak at least weekly, for hours at a time on the phone, Mr. Ripps said. Topics included a possible video game in which Ye ascended to heaven to meet his mother and Ye’s disdain for Drake.

“I felt like I was his best friend,” Mr. Ripps said.

Then, after about two months and just as suddenly as Ye had taken an interest, he backed off. Mr. Ripps received an email from Ye saying an exchange between the men had left him “stressed”; shortly thereafter, Ye told Mr. Ripps over the phone that their conversations had gotten too intense. (Ye did not respond to request for comment.)

Until, in late 2017, Mr. Ripps sent a picture of himself wearing a MAGA hat with the text written in Cyrillic script to an old iMessage account of Ye’s. Since the men had last talked, Ye had publicly aligned himself with President Donald J. Trump — a move his fans didn’t know whether to regard as an elaborate art project or a genuine shift toward the right.

Mr. Ripps thought his old collaborator would be amused by a joke about Russian interference in the 2016 election, and a reference to a Russophile trend in fashion. (Mr. Ripps, who had earlier posted to Instagram comically deformed portraits of Mr. Trump, Jared Kushner and Kellyanne Conway, seemed to regard MAGA as a set of potent symbols to manipulate.)

Almost immediately, Ye sent Mr. Ripps the contact card for his assistant — a sign he wanted to talk.

Soon, Mr. Ripps said, he flew him out to the Calabasas, Calif., headquarters of Yeezy, his fashion company. Ye told Mr. Ripps that he needed an interdisciplinary creative mind to hold all of his operations together, from fashion to music. It was as if they’d never stopped talking.

Ye had, by that summer, turned even further toward provocation; in May he drew widespread criticism for saying that slavery was a “choice” in an interview with TMZ.

Mr. Ripps said recently in an interview he didn’t approve of all of Ye’s comments, but that — from his experience in the gallery world — he “understood and sympathized” with someone becoming “controversial for stating his mind.” Within weeks of their meeting in Calabasas, Ye had hired Mr. Ripps at Donda, which encompassed Ye’s wildly ambitious projects extending beyond fashion and music into things like housing and manufacturing.

Mr. Ripps’s work for Ye culminated in October 2018, when, he said, he designed a presentation for Ye to give to President Trump during a private lunch. Though Mr. Ripps did not attend the meeting, the men flew to Washington together.

During the flight, Mr. Ripps said, Ye announced that he wanted to redesign Air Force One; Mr. Ripps googled “Aquatic Jet Israeli,” because, he later recalled, “the Israelis make dope stuff.” Mr. Ripps found a cool-looking glass-roofed aircraft, and showed it to his boss. Several hours later, Ye showed an image of the plane in the Oval Office in front of the president. He called it “iPlane.”

The grandiose presentation, complete with talking points, centered on a message of “Empowering America’s Core” and ended with a Photoshopped image of Mr. Trump and Ye standing in front of a giant Yeezy factory, superimposed in front of the Chicago skyline.

Mr. Ripps said that Ye regarded the meeting as a triumph, and sent Mr. Ripps an email comparing Mr. Ripps to Pablo Picasso, which The New York Times reviewed. (Ye has a habit of comparing people to Picasso, including himself and his architect.)

Then, just as suddenly as before, Ye soured. One day, Mr. Ripps said, he received a call from Ye — who has acknowledged being diagnosed with bipolar disorder but subsequently questioned the diagnosis — saying that he needed to take a break. Mr. Ripps, who had moved to Chicago for the job, received an email several weeks later from Ye’s lawyers informing him that his employment had been terminated. He had lasted four months.

Out of Ye’s orbit, and off his payroll, Mr. Ripps said he started to think harder about remarks he said Ye had made to him in 2018 about studying Nazis. Mr. Ripps is Jewish, and the comments had made him uneasy at the time, he said. But he had dismissed them, hopefully, as more of Ye’s provocative non sequiturs.

“I didn’t want him to be a Nazi,” he said.

And of course, Mr. Ripps’s association with Ye had helped his career. After leaving Donda, he continued to work for clients in the music world, including doing stage design for Pusha T and creative direction for Tame Impala’s tours.

In October 2022, after Ye made antisemitic remarks on social media and in a series of interviews, CNN reported that Ye had a long history of admiring Hitler. The next month, in an interview with NBC News, Mr. Ripps condemned the musician, calling his comments “dangerous and disgusting and actually violent.”

By that time, Mr. Ripps was already months into another call-out campaign against what he saw as bigotry at the center of pop culture.

‘As a Troll I Know It When I See It’

After a furious hype cycle in 2021 and 2022, the Bored Ape Yacht Club became the most prominent set of NFTs. Mr. Ripps was already interested in the technology, which was in his sweet spot of art, tech and buzzy nonsense. In particular, he focused on the way many NFT buyers misunderstood what they were really buying: not a digital image file, but the unique code underneath.

A friend of Mr. Ripps’s showed him an image of a Nazi death’s head insignia side by side with the skull logo of the Bored Apes. They looked, Mr. Ripps thought, exactly alike.

“As a designer I said, there’s no way this isn’t a reference,” Mr. Ripps said. “Every designer Google Image searches for reference. There’s too many matching characteristics for this to be an accident.”

First in a relentless series of tweets and then on a website he built to collate his findings, Mr. Ripps accused BAYC of larding its project with racist and antisemitic imagery and coded messages: One ape wore a headband from “fascist Imperial Japan,” he wrote; one of the co-founders went by the nickname Gargamel, which Mr. Ripps wrote was “a common term used on 4chan to discuss Jews”; the overall project, Mr. Ripps claimed, was an example of “simianization” — disparaging an ethnic or religious minority by comparing them to monkeys.

“As a troll I know it when I see it,” he tweeted on Dec. 31, 2021.

Last year, Mark Pitcavage, a historian and senior research fellow at the Anti-Defamation League, said that the connection between the skull logo and the Nazi skull was tenuous, and that other connections Mr. Ripps made were spurious.

(Since Mr. Ripps first made the accusations, Yuga Labs has repeatedly and at length denied them, without mentioning Mr. Ripps by name.)

But Mr. Ripps kept it up, an arch ironist apparently moved to five-alarm probity by the apes that were saturating the culture and selling for millions.

Last spring, he minted a new NFT that pointed to a copy of an existing Bored Ape image. Since then, Mr. Ripps and several collaborators have minted more than 9,000 such tokens, called “RR/BAYC,” which, according to an official statement, use “satire and appropriation to protest and educate people regarding The Bored Ape Yacht Club and the framework of NFTs.”

In June 2022, Yuga Labs sued Mr. Ripps and his collaborators for “causing actual and monetary harm to Yuga Labs and to the holders of authentic Bored Ape Yacht Club NFTs.” (The company separately sued Tom Lehman, another collaborator of Mr. Ripps’s and the co-founder of the website Genius; he has settled.)

Tellingly, the Ape creators didn’t sue Mr. Ripps for copyright, which protects creators from having their artistic or intellectual work stolen. Nor did Yuga Labs sue Mr. Ripps for defamation.

Rather, they accused him of violating their trademarks, which protect consumers from buying confusing knockoffs that inappropriately use a word, phrase or design that identify a product. (Think: logos.)

In a blow to Mr. Ripps’s defense, a federal court in California in December denied a request by his lawyers to dismiss the suit on the grounds that it was an attempt to chill his speech. Mr. Ripps has appealed that ruling.

Rebecca Tushnet, a professor at Harvard Law School and an expert in intellectual property law, said the court didn’t buy Mr. Ripps’s argument that his criticism of the Bored Apes justified his use of Yuga Labs’ trademarks. Sixty years after Warhol’s Campbell’s soup cans, appropriation art is still unsettled legal terrain — as a copyright case involving Warhol that the Supreme Court is expected to rule on shortly makes clear — and an argument as meta as Mr. Ripps’s can seem nebulous before the cutting simplicity of a trademark claim.

“It’s going to be hard for him to avoid liability,” Ms. Tushnet said. “Courts have always struggled with appropriation art, and the border between art and things that aren’t art.”

(In another recent case, the luxury brand Hermès won a judgment against a Los Angeles artist who sold NFT versions of its famous Birkin bag; the jury found that the NFTs weren’t entitled to First Amendment protection.)

When Mr. Ripps began his efforts, the Bored Ape creators were anonymous. In February 2022, their identities were made public by BuzzFeed News; two of them attended creative writing M.F.A. programs. As a result, Mr. Ripps has softened his stance that the founders are secretly far-wing extremists. Instead, he now sees them as unfunny: appropriative pranksters trying a grift.

“They think it’s some fun literary device because they’re writers and they think it’s edgy and interesting,” Mr. Ripps said. “Or it’s some inside masturbatory joke.”

Now, that joke may ruin Mr. Ripps, he said, at least financially. While he still has client work, and in February held a small show of found art in Los Angeles (a collection of cheap, branded knickknacks given to doctors by pharmaceutical companies), most of Mr. Ripps’s life now revolves around the case, on which he says he has already spent “hundreds of thousands” of dollars — “all of my money.” The case is set to go to a jury trial on June 27.

“There are some versions of appropriation art where getting punished is part of the art,” Ms. Tushnet said. “It could be both art and be illegal.”