Raiders Coach Made Racist Comment About N.F.L. Players’ Union Chief

DeMaurice Smith, the executive director of the N.F.L. Players Association, was denounced in racist terms in a 2011 email by Jon Gruden, who is now the coach of the Las Vegas Raiders.

The email surfaced just hours before the player representatives for the 32 teams were expected to vote on whether to give Smith a fifth term as the union’s leader without having to hold a general election. Smith was not endorsed by the union’s selection committee earlier this week, a sign that he faces unusually stiff opposition within his own ranks. Some players have accused Smith of being too conciliatory to the league.

There is reason to believe the league’s owners would prefer that he stay, and such an…