Las Vegas Raiders coach Jon Gruden in 2011 used racist terms to denounce DeMaurice Smith, executive director of the NFL Players Association, who is Black and is now facing opposition within the union to the extension of his contract.

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

There is reason to believe that the league’s owners prefer that he stay, and such an inflammatory email, first reported by The Wall Street Journal and confirmed by The New York Times, complicated the vote for players who opposed Smith.