Former Ropes & Gray associate John Ray III testified in a Boston federal courtroom Friday that he sent a May 2011 email to the firm seeking $21.5 million to settle his retaliation charge because he wanted “to have a discussion.”

“I was thinking, let’s sit down and let’s talk,” Ray said during cross-examination by Ropes lawyer Michael Keating, litigation department chairman at Boston’s Foley Hoag.

Ray took the stand for nearly three hours to state his claim that the firm retaliated against him for complaining about racial discrimination. Two Ropes partners withheld promised letters of recommendation, he said. And as tensions between the parties escalated, the firm released the Equal Employment Opportunity Commission’s initial denial of his discrimination claim to the Above the Law website in May 2011. That letter contained some of Ray’s confidential personal information.

Ray joined Ropes in 2005 after working at Cravath, Swaine & Moore and Jenner & Block. In December 2008, Ropes told him he would be paid six-months’ severance while he looked for a new job. Ray claimed partners had cut his assignments that year after he complained about a “nigger” joke and a partner’s request that he serve as the “token black associate” during a meeting with a prospective bank client.

In January 2011, the EEOC found that Ropes had not discriminated. But the next month, the agency held that Ropes had retaliated against Ray for filing the discrimination complaint. That August, Ray filed a federal racial discrimination and retaliation case against the firm, 13 of its partners and its former “chief people officer.”

Two years later, U.S. District Judge Richard Stearns in Boston granted summary judgment to Ropes on most of Ray’s claims. But the retaliation claim survived.

Ray appeared amiable during much of the questioning by his lawyer, Latif Doman of Washington’s Doman Davis. When Doman asked about Above the Law’s report, Ray paused and appeared to struggle to control his emotions.

Ray said he sought money because the firm “destroyed 15 years of my work. On top of that, they piled a personal attack on me that destroyed my reputation. It went out to friends. It went out to thousands of lawyers across the country. It was something I was never going to get away from.”

U.S. District Judge Richard Stearns sustained a few of Keating’s objections to Doman’s questions or references to information excluded from the trial. A couple of times, he told Doman to “tread carefully” or “tread lightly.”

Keating emphasized certain statements Ray made in emails to Ropes in 2011 before the Above The Law report. “You wanted to use that final determination to pressure Ropes & Gray into paying you a substantial amount of money,” Keating said.

He noted that Ray had warned that he would alert bar disciplinary agencies in Massachusetts, New York and elsewhere and seek criminal charges against Ropes partners David Mandel and Brien O’Connor. “You were telling Mr. Mandel that as a consequence of these steps you were going to take with bar associations they were going to be called upon at some time to defend themselves to the public,” Keating said.

Ray said he referred to the possibility of a trial, “like right now.”

“At some point, I wanted them to stop—to just end this,” he said.

Keating played two short video clips of Ray’s deposition testimony about letters he sent to members of the Massachusetts congressional delegation and Harvard Law School people and organizations. “All of this happened before Above the Law ever printed one word about you,” Keating said.

Ray was due to return to the stand on Monday.

Sheri Qualters can be contacted at