Ugly off-field times for former Bucs coach.

[UPDATE: 9:26 p.m.] Former Bucs Super Bowl-winning coach Chucky got in hot water last week. Someone leaked an e-mail to the Wall Street Journal from Chucky to Bruce Almighty, the former Bucs general manager who at the time of the e-mail worked for Washington.

The email contained raciallly-charged language mocking NFLPA big shot DeMaurice Smith by Chucky.

Well, now it’s worse.

Chucky’s original e-mail in question was leaked on Friday. Today, additional e-mails were shared by the New York Times and they paint Chucky in an even less flattering light.

Chucky apparently went on a homosexual screed in a group e-mail that included potshots at Caitlyn Jenner, NFL commissioner Roger Goodell, then-vice president Joe Biden, Bucs co-chairman Bryan Glazer and Smith, reports Ken Belson and Katherine Rosman of the New York Times.

… Gruden crudely asked Allen to tell Bryan Glazer, whose family owns the Tampa Bay Buccaneers where Gruden coached until 2008, to perform oral sex on him. Allen said Glazer would “take you up on that offer.”

The e-mails were sent while Chucky was an analyst on Monday Night Football broadcasts.

Also, the New York Times writer surely implies that within the group e-mails “pornographic images” were shared.

Now Joe knows Chucky is very, very bitter at Team Glazer for firing him in January of 2009. He played up his juvenile “Fired Football Coaches Association” schtick apparently unaware that coaches far, far more accomplished were also fired. Those included Paul Brown, Tom Landry and Don Shula, among others.

Chucky even had a crude reference once about Bucs co-chairman Joel Glazer while speaking to a group in Ocala a handful of years ago.

It’s one thing to have it revealed that a head coach was involved in an unsavory issue (even 10 years ago) and to move on from that. Now, just when the Chucky reference to Smith may have begun to dial down, Chucky and the Raiders are hit in the face with possibly worse allegations.

Given that all of Allen’s e-mails have been sifted through by NFL investigators in relation to the sexual misconduct allegations against Washington’s front office last year, Joe has to wonder what else will be learned from other Chucky’s e-mails?

That’s where Chucky is really in a pinch. Bad enough he was stupid using an obnoxious racial reference to Smith. Now it comes out Chucky wanted his former employer, an NFL co-owner, to perform a lewd act on him in a rant about homosexuals. Raiders owner Mark Davis has to wonder what else is coming down Las Vegas Blvd., and when?

Chucky surely cannot lean on his record in his second stint with the Raiders to help bail him out.

[UPDATE: 9:26 p.m.] Per Mike Florio of ProFootballTalk.com, Chucky has resigned.

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