The proceedings included one period open to the public, which was then followed by a session during which the sides remained behind doors while attempting to find common ground on a potential settlement on Brady's four-game suspension. Lawyers for the two sides agreed to meet again Thursday with New York Federal Court Judge Richard Berman, court documents showed.
"We won't be making a formal statement other than to say that we had a productive day in court, and we'll get back to work on the issue. Thank you," NFLPA Executive Director DeMaurice Smith said after the conference.
The public portion of the day opened with pointed questions from Berman to attorneys for both the NFL and NFLPA.
Speaking on NFL Network, Director of the Tulane Law Sports Program and NFL Media legal analyst Gabe Feldman, who was in attendance, noted that the judge hit on the settlement pressure points.
"I think that it was a big part of the purpose of this morning was for the judge to poke holes in both sides," Feldman said. "To say, I have some serious questions about both of your cases and I could rule against each of you based on the questions I have. So rather than risk losing it all, rather than risk a worst-case scenario, why not move a little bit in toward something of a settlement rather than face my decision."
According to NFL Media's Judy Battista, NFL attorney Daniel Nash was repeatedly questioned whether there was direct evidence linking Brady to deflated footballs.
Questioning phrases used in the Wells Report such as, "more probable than not" and "at least generally aware," Berman stated: "I don't know what that means."
Per Feldman, Nash's response to the line of questioning was that it doesn't matter what any of us think of the underlying evidence. The Commissioner was given the power under the collective bargaining agreement to determine what is in the best interest of the NFL, and this matter gets to the heart of competitive advantage.
Berman then questioned NFLPA attorney Jeffery Kessler as to why two low-level Patriots employees would act independently and deflate footballs without Brady's knowledge, saying, "He's the one who throws the ball."
Another line of questioning centered on why Brady didn't cooperate with the investigation, to which Kessler admitted Brady could have conducted himself differently with Ted Wells. Kessler said Brady did not cooperate at the time based on the advice of his agent Don Yee, not the NFLPA, which Feldman believes could open the door for a possible settlement if both sides are willing to find the common ground.
"I think the questions were clearly designed to create fear on both sides (they could lose the case)," Feldman said.
Feldman pointed out that Berman asked the NFL questions for roughly 45 minutes, while the judge only asked Brady's side questions for 25 minutes. Feldman said not to read much into that difference.
Prior to Wednesday's settlement conference, Berman also set a potential Aug. 19 date for both parties to meet again and either continue to conference or hear oral arguments.