"Instead of having a nice double date, we dated [agent Drew] Rosenhaus and Antonio Brown," Gruden said.
Rosenhaus first called Steelers general manager Kevin Colbert about Brown's desire to be traded on Dec. 31, the day after the 2018 regular season concluded, Rosenhaus told ESPN.
In the early hours of March 8, NFL Network reported the Bills were "closing in" on a deal for Brown, who quickly called any deal with Buffalo "fake news" on social media.
The Raiders did a "deep dive" into what happened between the Steelers and Antonio Brown before making the trade, according to GM Mike Mayock.
Rosenhaus left Brown's home in Miami that night thinking a deal might be off completely and new teams would need to emerge.