A Manhattan federal judge has ordered The New York Times Co. to turn over emails with its outside counsel regarding its decision to terminate a "full-time freelancer" who worked with the paper as a photographer for 10 years.

U.S. District Judge Paul G. Gardephe of the Southern District of New York on Friday ruled that the Times could not withhold two emails it exchanged with its attorneys from Proskauer Rose because the paper's defense in the misclassification, discrimination and retaliation suit centered on advice it had received from counsel.

According to court documents, the Times had disclosed 31 partially redacted documents and 23 emails that it had held back altogether in discovery, after Gardephe made it choose between withholding the documents and asserting in court that its attorneys had advised the Times to cut ties with the paper based on his involvement with an organization he founded, called Copyright Collective.

However, the company still refused to produce two emails with Proskauer, claiming that attorney-client privilege still applied.

Gardephe said the Times had already waived attorney-client privilege in order to pursue its defense, and that emails it chose not to produce covered the same subject matter.

"Defendants have offered no argument as to why they have not effected a subject matter waiver, nor have they explained why the fact that the two remaining documents contain communications between the Times and its outside counsel—rather than communications involving only in-house counsel—is of any legal significance," he wrote in a seven-page opinion that directed the Times to produce its emails "forthwith."

Lee Bantle, who represents plaintiff Robert Stolarik in the case, said the issue had been correctly decided, but that the ruling also showed the "sort of precarious position employers are in" if they make termination decisions on the advice of counsel.

"They may then have to disclose that advice in litigation," said Bantle, of Bantle & Levy in Manhattan.

An attorney for the Times did not immediately respond late Friday to a call seeking comment on the ruling.

Stolarik sued the paper and its assistant managing editor for photography in 2017, claiming that the Times had stopped assigning him work based on his age and arrest record. Stolarik, who was 47 at the time, also claimed that he had essentially worked full-time hours for the paper and that it had improperly classified him as a freelancer and independent contractor.

The Times contended that Stolarik's termination was the result of actions he took on behalf Copyright Collective, which pursues royalties from entities that use photographs without permission. The paper said that its Proskauer lawyers had recommended the move because Stolarik had threatened litigation against entities that had licensed photos from the Times.

Bantle denied that Stolarik had been aggressive in the interactions and said he planned to litigate the case through trial.

In an interview, Bantle said the Times had purposefully misclassified his client's status with the company and noted the irony of the paper's stance toward Stolarik, given some of the positions it had taken on its editorial pages.

"It's a very important case in terms of misclassification of employees, and we think Robert Stolarik was misclassified for 10 years by the New York Times," he said. "They keep publishing editorials that companies shouldn't do that, but then they keep doing it themselves."

Stolarik is also represented by Sherie Nan Buell and Harrison David Krauss, also of Bantle & Levy.

The Times is represented by Allan Bloom, Michelle A. Annese, Russell L. Hirschhorn, Gregory Rasin and Myron D. Rumeld of Proskauer.

The case is captioned Stolarik v. The New York Times.

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