3 most controversial Jon Gruden moments of all time

Well... it didn't take long for the ball to drop on Jon Gruden. In the wake of his initial discovered email from 2011 in which he disparaged NFLPA executive director DeMaurice Smith, the league has found several other emails that are just as disgusting.

To begin with, the first email, which was about DeMaurice Smith, was inflammatory in the way that Gruden described him. Smith, who is African American, was described by Gruden, who is Caucasian, as stated:

"Dumboriss Smith has lips the size of Michellin (sic) tires."

For anyone not up to snuff on the history of race relations in the past, African Americans were often depicted as having large, oversized lips and typically typecast as ignorant or not smart.

For Gruden to make such comments was absolutely disgraceful and embarrassing, not only to himself but to his family and the entire NFL community. As it turns out, this was the first of several disparaging emails that Gruden "thought" he sent in confidence.

In other emails, which were also sent in 2011 during the NFL lockout, Gruden's words were found to be homophobic and misogynistic. As such, he chose to resign as an obvious cop out to avoid being fired.

There have been several measured responses to the news. One of those comes from media pundit Jason Whitlock in the form of a tweet.

Before we take a look at Gruden's three most controversial moments, let's take a look at some of the reactions from the Twitterverse.

3 most controversial Jon Gruden moments

#1 - Email-Gate

For Jon Gruden and controversy, nothing can top the news of the last 12-24 hours. Gruden had some scathing emails back in 2011 during the NFL lockout that were racist, homophobic and misogynistic in nature.

In one of the emails, he demeaned African American NFLPA executive director DeMaurice Smith by calling him "Dumboriss" and by saying he had "lips the size of Michellin (sic) tires." He also used terms such as "queer" and "faggot" in the most derogatory ways possible.

I'm sure I speak for the masses when I say "good riddance, Jon Gruden!"

#2 - Winning a Super Bowl with Tony Dungy's players

Back in 2002, Gruden took over as coach of the Tampa Bay Buccaneers. Their previous coach, Tony Dungy, was the coach there from 1996-2001 and had built a more than respectable roster.

Before Dungy's arrival, the Bucs were the laughing stock of the league. That was until he drafted players such as Warren Sapp, Derrick Brooks and John Lynch and made them Super Bowl contenders.

Dungy was on the cusp of taking the Bucs to the Super Bowl before he was ousted. Gruden entered in 2002 and won the Super Bowl with Dungy's team and defensive formula for success.

#3 - Raiders owner Al Davis becomes enemies with Gruden

Before his stint with the Buccaneers, Gruden cut his teeth in the league as a head coach with the (then) Oakland Raiders. Al Davis, longtime owner of the Raiders, initially hired Gruden because of his youthful exhuberance and his unique take on calling plays.

However, after four seasons with the Raiders, Davis became disillusioned by the lack of a vertical passing game, which is something the Raiders were traditionally known for. Gruden preferred a horizontal attack with drags and screens. The relationship soon soured and he was off to sign with the Buccaneers.

This goes without saying but the there is no place in the league (or in our world for that matter) for the rhetoric displayed by Gruden in the emails. The Raiders now have a tall task ahead of them but they will be better off with anyone else in his place to lead the men into battle on Sunday.

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