By Robin Sidel 

A federal judge rejected a proposed class-action settlement between American Express Co. and a group of merchants, citing a recent discovery that a lawyer who represented retailers in the case shared confidential documents with a rival attorney who was working for MasterCard Inc. in a similar matter.

In a 44-page decision released Tuesday morning, U.S. District Judge Nicholas Garaufis also removed the retailers' lawyer, Gary Friedman, from the case, citing his "improper and disappointing conduct" that "fatally tainted the settlement process."

The move by Judge Garaufis, sitting in the eastern district of New York in Brooklyn, was particularly significant because he had granted preliminary approval to the $79 million settlement last year.

The exchange of documents between Mr. Friedman and Keila Ravelo, a former lawyer at Willkie Farr & Gallagher LLP who represented MasterCard, is also muddling a $6 billion settlement between Visa Inc., MasterCard and many of the same merchants. That settlement has already been finalized, but lawyers representing retailers last week started the process of trying to unravel it, citing the raft of emails between Ms. Ravelo and Mr. Friedman.

The two lawyers were close friends who had previously worked together.

It isn't clear if Judge Garaufis' decision in the AmEx case will have any implications for the Visa and MasterCard settlement, which has been handled by a different judge in the same Brooklyn court. Mr. Friedman, who led a group of plaintiff lawyers in the AmEx case, held a lesser role in the case involving Visa and MasterCard.

Mr. Friedman, who runs a firm called Friedman Law Group LLP, couldn't be reached for comment. Judge Garaufis also removed the entire firm from the case. Lawyers representing Mr. Friedman also couldn't be reached.

AmEx inked the $79 million settlement with the merchants in 2013. In addition to the payout, the pact would give merchants the right to surcharge customers who use an AmEx credit card or charge card.

In a statement, AmEx said it was disappointed by the rejection and "we continue to believe the agreement was fair to merchants and would provide them with additional flexibility while ensuring our card members are treated fairly at the point of sale." The company also said it would continue to fight the case in court.

In his decision, Judge Garaufis said that he didn't need to consider other objections to the proposed settlement that were raised by some merchants because "the procedural unfairness and failure of adequate representation revealed by the Friedman/Ravelo communications requires disapproval of the settlement."

He also described Mr. Friedman's conduct as "egregious," saying the lawyer sent emails containing "confidential and highly confidential information of American Express" to Ms. Ravelo. The judge also noted that the exchange of emails wasn't accidental because Mr. Friedman wrote "burn after reading" in at least two of them.

The rejection of the settlement represents Judge Garaufis' second recent blow against AmEx. Earlier this year, he ruled that AmEx's rules that prevented merchants from steering customers to cheaper cards were anticompetitive. AmEx is appealing that decision, but merchants are now permitted to encourage customers to use other cards from Visa and MasterCard.

Write to Robin Sidel at robin.sidel@wsj.com

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