One of the many twists on the winding road to Colin Kaepernick’s unusual tryout on Saturday was a series of conversations between two unlikely bedfellows.

Since they formed a business alliance this summer, Jay-Z, the music star and impresario, and Roger Goodell, the N.F.L. commissioner, have spoken frequently about several issues, including the fate of Kaepernick, the former San Francisco 49ers quarterback who has not played in nearly three years, after kneeling during the national anthem in the 2016 season.

Kneeling made Kaepernick, 32, a polarizing force across the country. He began doing it to protest police violence against African-Americans, then became a free agent in 2017 and was unable to find a new club. After that, he filed a grievance accusing the league’s 32 owners of conspiring to keep him off the field because of his political views.

The league reached a multimillion-dollar settlement with Kaepernick in February, a move that gave teams in search of a quarterback — and there are many with needs at that position — a green light to give Kaepernick a tryout. To date, no one has, and Kaepernick has largely been out of the spotlight this season, a relief to many team owners who wanted to move beyond the debates he had kindled.