Mr. Delakas began running the newsstand in 1987, paying weekly fees of $75 and up to the license holders, first Stella Schwartz and later her sister, Katherine Ashley. Although Mr. Delakas said that he saw nothing wrong with the arrangement and never tried to hide it, officials at the Department of Consumer Affairs said it violated the city administrative code, which states that newsstands may be operated only by those with licenses and that licenses are not transferable without approval. When Ms. Ashley died in 2006, her will bequeathed the newsstand license to Mr. Delakas, but rules at the time allowed transfers only to family members, officials said. So the department instead turned the license over to Ms. Ashley’s husband, Sheldon Ashley, who allowed Mr. Delakas to continue running the newsstand.

After Mr. Ashley died in 2010, Mr. Delakas applied for a license to run the stand. City officials declined his request and a judge upheld their decision, noting that Mr. Delakas had engaged in a “fraudulent arrangement” with the Ashleys. In December, the city padlocked the stand, saying it had been operating illegally.

Mr. Delakas’s lawyer, Arthur Schwartz, said he was filing a new license application and appealing the order locking the stand. On Wednesday, he said, a State Supreme Court justice will hear arguments on whether the stand should be reopened while the appeal is pending. But city officials maintain that it is time for Mr. Delakas to leave.

“Four separate courts have rejected Mr. Delakas’s claim that he is entitled to this newsstand,” Katyusca Abreu, a spokeswoman for the Department of Consumer Affairs, wrote in an email, adding that the agency “will now be able to offer the newsstand to licensed operators who have been displaced” from other areas.

Mr. Delakas’s allies have accused the agency of being too punitive. One of them, Martin Tessler, who lives around the corner from Astor Place and once led community campaigns against noisy music there, said that “the letter of the law is overruling the spirit of the law.”