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.Jason Whitlock@WhitlockJasonWe can't remain this weak and phony. Jon Gruden saying DeMaurice Smith has huge lips, which he does, can't bring us to tears. Are we really this weak? Does the white man's opinion of our lips mean that much? I like my big lips, never had a woman complain about them. twitter.com/espn/status/14…ESPN@espn"For us to be moving back and not forward ... National Football League, this hurts me."A powerful conversation from the Sunday NFL Countdown crew on Jon Gruden’s 2011 email that included a racist comment in reference to NFLPA executive director DeMaurice Smith:12:29 PM · Oct 10, 20213306422"For us to be moving back and not forward ... National Football League, this hurts me."A powerful conversation from the Sunday NFL Countdown crew on Jon Gruden’s 2011 email that included a racist comment in reference to NFLPA executive director DeMaurice Smith: https://t.co/FQvMGFUfOjWe can't remain this weak and phony. Jon Gruden saying DeMaurice Smith has huge lips, which he does, can't bring us to tears. Are we really this weak? Does the white man's opinion of our lips mean that much? I like my big lips, never had a woman complain about them. twitter.com/espn/status/14…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.Dex Hinton@DexHintonGruden’s QB Camp but it’s just him looking at their old tweets.9:39 AM · Oct 11, 2021175Gruden’s QB Camp but it’s just him looking at their old tweets.Kev Mahserejian@RotoSurgeonhey, at least Gruden didn’t get got by old tweets🤷🏻‍♂️9:31 AM · Oct 11, 202114hey, at least Gruden didn’t get got by old tweets🤷🏻‍♂️tinsley@AgentTinsleyI haven’t watched the NFL since they did Kaep dirty but all I hear tonight reading my timeline is Jim Rome’s voice saying “RAIDER FAN” when I see Gruden tweets. Guy in the office next to me at my first agency job used to listen to him all the time on the radio.9:34 AM · Oct 11, 20214I haven’t watched the NFL since they did Kaep dirty but all I hear tonight reading my timeline is Jim Rome’s voice saying “RAIDER FAN” when I see Gruden tweets. Guy in the office next to me at my first agency job used to listen to him all the time on the radio.Tariq 🎲@KinggRiqY’all see Gruden, y’all better delete them tweets9:19 AM · Oct 11, 2021Y’all see Gruden, y’all better delete them tweetsRCKLSS®🇭🇹@StevenV35Gruden was letting those emails fly like they were tweets in 2012 man was offending everybody 😂9:16 AM · Oct 11, 20212Gruden was letting those emails fly like they were tweets in 2012 man was offending everybody 😂Ben Stevens@BenScottStevensPlease, at the absolute least, keep the Jon Gruden to USC tweets in your drafts.9:18 AM · Oct 11, 2021191Please, at the absolute least, keep the Jon Gruden to USC tweets in your drafts.Christian Hietanen, DO@DrHietanenDo yourself a favor and don’t read the replies in any of these tweets about Gruden resigning.9:09 AM · Oct 11, 20212Do yourself a favor and don’t read the replies in any of these tweets about Gruden resigning.Thomas Christopher@ThomasCP_NFLToo many Jon Gruden tweets and not enough Dan Snyder tweets.@nflcommish at it again!9:01 AM · Oct 11, 20213Too many Jon Gruden tweets and not enough Dan Snyder tweets.@nflcommish at it again!Bridget@denbron77Once again looking at tweets of people defending Gruden and happy I’m not following them. 🤮8:57 AM · Oct 11, 202144Once again looking at tweets of people defending Gruden and happy I’m not following them. 🤮Gabriel Carrera@Gabriel7DB4L@denbron77 Not sure how anybody can defend what he said. Craziness that I want NO part of.8:59 AM · Oct 11, 20212@denbron77 Not sure how anybody can defend what he said. Craziness that I want NO part of.3 most controversial Jon Gruden moments#1 - Email-GateFor 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 playersBack 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 GrudenBefore 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.Also Check Out: Complete NFL Bye Weeks 2021 Schedule