Odds Say Jon Gruden’s Raiders Tenure is Short-Lived

By Eric Rosales in NFL Football
Updated: April 6, 2020 at 6:57 pm EDTPublished:

- Jon Gruden’s second tenure with the Raiders may be short lived
- Can Chucky guide the Raiders to a Super Bowl appearance?
- Does the head coach make it past next season?
This probably wasn’t the return to head coaching Jon Gruden or Raiders fans were expecting. Unfortunately, it’s been more of the same mediocrity that’s plagued the franchise for decades now.
Prior to their Week 7 bye, we last saw the Raiders get ripped by the Seahawks, in Oakland’s most lopsided loss of the year, dropping them to 1-5.
https://twitter.com/WilliamSlavik2/status/1055530306336382976
All they have to hang their hat on is a win over the Browns – a game Cleveland could argue they got jobbed out of.
Browns caught a couple breaks today, but Raiders got really lucky here. Should’ve been a Derek Carr fumble recovered by Cleveland, possibly returned for a TD. pic.twitter.com/gBPQY7J2U2
— Matt Schneidman (@mattschneidman) October 1, 2018
With a move to Vegas looming, and a roster bereft of top talent, it’s already time to discuss Gruden’s staying power. Remember this dude inked a 10-year, $100 million deal to return to coaching.
Sportsbooks have joined the discussion, with some numbers for us to consider. Let’s do this.

Odds Jon Gruden Will Lose His Job as Raiders Head Coach
When Will Jon Gruden Lose His Job | Odds |
---|---|
Before End of 2019-20 Season | +200 |
After End of 2019-20 Season | -300 |
They’re giving Chucky the benefit of the doubt, at least to complete a second season with the Silver and Black. Much of that has to be based on the fact that Oakland will have three first round draft picks next year.
Jon Gruden finally has three first round picks to trade for an elite pass rusher.
— Kevin Clark (@bykevinclark) October 22, 2018
Of course, the reason they have those extra picks is due to trading all-world linebacker Khalil Mack, who is currently in the running for NFL Defensive player of the Year, just prior to the start of the season. The other is the most recent deal, shipping promising receiver Amari Cooper to the Cowboys.
Jon Gruden on Amari Cooper in February: “He’ll be the focal point of our offense.”
Jon Gruden on Amari Cooper Trade Rumors Last Week: "I haven't heard that. I'm just sorry to have to deal with a lot of these reports.”
Today: Raiders trade Amari Cooper
— CBS Sports (@CBSSports) October 22, 2018
If Gruden hits on those picks, he could have himself some nice cornerstones to add to Derek Carr. If they are not impact picks and the Raiders falter again, this marriage could end early.
The pick: After end of 2019-20 Season (-300)
Odds Jon Gruden Takes the Raiders to the Super Bowl
Yes | No |
---|---|
+500 | -900 |
As of this season, there’s about a 1000% percent chance that you’d lean towards the no, and who could blame you? But we’re just a few years removed from Oakland coming out of nowhere to post a 12-4 mark. If not for Carr breaking his leg at the end of the regular season, the Raiders could have been in business.
Heartbreaking! 💔
Listen to the moment @RAIDERS quarterback Derek Carr knew he had broken his leg – https://t.co/LdhaQKq44x #RaiderNation pic.twitter.com/ruUjaUzZpI
— NFL UK & Ireland (@NFLUKIRE) December 29, 2016
Again, much will depend on Gruden’s roster building ability, which currently appears lackluster. But the NFL prides itself on parity, and let’s be honest: if you can make the playoffs, you’ve got a legit shot.
If he can survive the lean times, he’ll have plenty of shots to make it. I’m playing the long game here, folks.
The pick: Yes (+500)
Odds Jon Gruden Wins a Super Bowl with the Raiders
Yes | No |
---|---|
+700 | -1400 |
While I do think there’s a value bet in making the game, it’s that much harder to win the whole thing.
And here’s what might be the kiss of death, or the eventual breakthrough that needs to happen, depending on your perspective: no head coach has yet to lead two different franchises to Super Bowl titles.
How it feels to win the Super Bowl (ft. Jon Gruden) 😂 #TBT https://t.co/1lSLP9HfH2
— The Checkdown (@thecheckdown) December 28, 2017
If he were to get there, Gruden would find himself on quite a short and elite coaching list: Don Shula, Dick Vermeil, Bill Parcells, Dan Reeves, Mike Holmgren, and John Fox. I don’t think he’s going to be the first name on a new list, though.
The Pick: No (-1400)
Odds Jon Gruden Resigns or Gets Fired
Scenario | Odds |
---|---|
Jon Gruden Resigns | -120 |
Jon Gruden Gets Fired | -120 |
Sportsbooks saved the best one of the bunch for last, and it’s a toss up.
In Gruden’s first stint with the Raiders, he forced his way out of Oakland and Al Davis eventually dealt him to the Buccaneers for two first round picks, two second round picks, and some cold, hard cash.
Gruden would win a Super Bowl with Tampa Bay, but when that run soured, he was fired and found his way into the Monday Night Football booth.
Gruden will be able to control his own fate for the first time in his career, and be able to walk away on his own terms.
Chucky has had many offers to return to coaching over the years, and it appears he made sure that he would have some type of control over personnel and front office decisions when he did.
With that sort of leverage, if he can find any type of success next year, he could control his own fate for the first time in his career. Crashing and burning, however, leaves him susceptible to getting axed.
As of today…the #Raiders would own:
No. 4 overall
No. 10 overall (Cowboys)
No. 17 overall (Bears)— Matt Miller (@nfldraftscout) October 25, 2018
Again, it’s all contingent on getting things righted on the field. As always, winning seems to cure all ills.
The pick: Jon Gruden Resigns (-120)

Sports Writer & Editor
Having worked in and around sports since 1997, Eric is truly a knowledgeable expert. The two-time journalism grad specializes in all things NBA and NFL. From TSN.ca to CTV's Olympic Broadcast Consortium, Eric's work has appeared in local and national publications alike.