50 Cent’s attorney faced a brutal grilling from New York appeals court judges as he argued that the star deserved to automatically win a lawsuit he filed against an ex-girlfriend over her “tell-all” Instagram posts.

The rapper sued Shaniqua Tompkins last year, claiming her videos violated an agreement she signed in 2007, in which she allegedly sold the star her life rights in perpetuity. Her lawyers fired back in January that she was coerced into signing the deal with threats and intimidation.

50’s lawyers are currently asking a state appeals court to grant him a victory in the case by “default,” citing the fact that it took Tompkins months to respond to the case. But at a court hearing Thursday (June 12), that argument got a chilly reception from a panel of five appellate judges, who sharply noted there was “no indication” that Tompkins had ever even seen the lawsuit.

“So counsel, you’re asking for a default judgment for four months’ delay, where it doesn’t even appear that the defendant was served properly. Is that right?” one judge asked 50’s attorney, Josh Reisberg of the firm Blank Rome, before he could even begin his presentation.

Though Reisberg responded that he disagreed with that “characterization” of the case, the judges then harshly questioned him throughout the hearing, showing an unusual level of skepticism that at times bordered on hostility.

Reisberg argued that 50 Cent’s process servers had tried multiple addresses for Tompkins that they had pulled from digital databases, but the judges quickly demanded to know what proof he had that they’d tried locations “where she actually lived.”

“I’m trying to understand: How did you make a [proper] showing other than saying ‘Oh, these are the addresses’?” one judge asked. “I could say that about anybody. You can’t believe everything that’s on the internet about all our addresses.”

Reisberg did not immediately return a request for comment from him or his client.

50 Cent’s publishing company, G-Unit Books, sued last year after Tompkins, the mother of his child, Marquise Jackson, went viral with a series of Instagram posts commenting on the criminal trial of Sean “Diddy” Combs. The videos touched on the rapper’s infamous 2000 shooting, as well as his long-running feud with Combs.

In taking her to court, 50 Cent’s attorneys said his company had paid Tompkins $80,000 in 2007 in return for “all rights to exploit her life story” — a deal they explicitly say was meant to protect the rapper’s reputation.

“Jackson purchased these rights to preserve them for use in future biographical or autobiographical projects, but also in part because he was concerned that Tompkins would attempt to monetize their history and his name,” the rapper’s lawyers wrote at the time. “His concerns were ultimately proven correct.”

In January, Tompkins finally responded to the case, saying she had never been properly served with it. If given the chance to fully rebut 50 Cent’s accusations, she said she would be able to easily do so because the contract she signed had clearly been invalid.

“The agreement was presented as a take-it-or-leave-it ultimatum, and I was given no opportunity to seek independent counsel or negotiate any terms,” Tompkins wrote in an affidavit at the time. “Fearing for my life and for my children’s lives, I signed the agreement under extreme duress.”

But owing to Tompkins’ delayed response, 50 Cent’s lawyers asked the judge for a default judgment, saying she had missed her shot to fight the case with such a response. The judge ultimately denied that request, prompting the rapper’s lawyer to file the appeal to the appellate court.

Following Thursday’s hearing, that appeal appears unlikely to succeed. After suggesting that Reisberg had “essentially” admitted that Tompkins wasn’t properly served, the judges then hammered him on whether his client had suffered any real prejudice — meaning, whether the delay had caused any problems for 50’s lawsuit. When Reisberg responded that such prejudice exists “in every case in which a defendant fails to appear,” the panel quickly cut him off.

“No. No. That’s not the case,” one judge told him. “So I’ll just let you know: That’s not the case.” The judges later told Reisberg that public policy favors allowing defendants a chance to defend themselves, a point that he did not refute. “There’s no prejudice here,” another judge asked him. “Why not go to trial?”

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