Ranking Jon Gruden’s best quotes in his Raiders return, from Khalil Mack to Tom Cruise

Jon Gruden’s return to coaching hasn’t been smooth, but he’s given us a few quotes to enjoy — especially about Khalil Mack.

When the Oakland Raiders hired Jon Gruden in January, they weren’t just getting a coach — they were getting a character and the show that comes with it.

After nine years as an ESPN personality, Gruden’s return to coaching has brought with it hilarious quotes on a weekly basis. And that’d be a lot more fun for Oakland if it was paired with some wins, but so far the Gruden era has just been a couple of losses and a skunked up locker room.

Judging by his record-breaking contract, the Raiders are probably going to have Gruden around for a while, and that means we’ll have some fun press conferences along the way. So far, these are the best quotes from Gruden since his 2018 return to Oakland and it’s a list we’ll keep updating as he keeps talking:

6. Let’s throw the game back to 1998

The quote: From a meeting with reporters at the 2018 NFL Combine:

“I’m trying to throw the game back to 1998. There’s a stack of analytical data ... that people don’t even know how to read. It’s one thing to have the data, it’s another thing to know how to read the damn thing.

“So I’m not going to rely on GPSes and all the modern technology. I will certainly have some people that are professional that can help me from that regard. But I still think doing things the old-fashioned way is a good way. And we’re going to try to lean the needle that way a little bit.”

The context: Gruden took over as head coach of the Raiders in 1998 and spent four seasons with the team before he was traded to the Buccaneers. After the 2008 season, he was fired by Tampa Bay and didn’t return to the coaching ranks, instead opting to join ESPN as a color analyst during Monday Night Football broadcasts.

So when he said he wants to throw the game back two decades, it was mostly a joke about recreating his first successes in Oakland. But it also has a fair amount of truth to it.

After all, he loves watching the Wisconsin Badgers’ run-first approach, he’s all about fullbacks, and doesn’t want to over do it with analytics.

5. Gruden isn’t overpaid. Tom Cruise is overpaid.

The quote: From a training camp conversation with NBC’s Peter King:

“I’m not making $100 million, just so you know. Well, I never thought Tom Cruise, never thought his movies were any good but he’s making plenty of money. There’s a lot of things that I don’t understand. No disrespect to Tom Cruise. I’m sure he’s a great actor. But you know what? You just go about your life as hard as you can. You try to find something you love and you do the best you can at it. I never got into coaching for the money. I got into coaching because I wanted to be a quarterback coach. What the salary cap has become, what free agency has become—it’s amazing.”

The context: Unlike NFL player contracts, we don’t usually get to see the breakdown of a coach’s contract. So it’s hard to know what exactly he means when he says he isn’t making $100 million.

According to ESPN’s Adam Schefter, Gruden received a 10-year, $100 million when he was hired in January. So maybe reaching that full $100 million requires reaching some incentives, or maybe Gruden’s just playing the semantics card because his salary is really $10 million per year.

Either way, calling Tom Cruise overpaid is kind of fair, I guess. He got $22 million to be in The Mummy reboot a couple years ago and that was awful. But come on, coach, you don’t think any of his movies are good? You ever seen Rain Man? Risky Business? A Few Good Men?

Cruise isn’t on Forbes’ list of the top five overpaid actors, so maybe Mark Wahlberg’s a better choice.

4. Gruden won’t take a salary if the Raiders don’t win

The quote: From an interview with USA Today in July:

“If I can’t get it done, I’m not going to take their money.

“Who guarantees I’m going to live 10 years? So I don’t think about that. You start thinking about a 10-year contract – people don’t know how it’s structured and it doesn’t matter. The only thing that matters is, ‘Is Khalil Mack going to be here? Is Donald Penn going to be ready to play?’ I’ve got more important things to worry about than eight years of my contract.”

The context: This one is pretty self-explanatory. Gruden’s reportedly making $100 million over the next 10 years, but wants to earn his sizable paycheck. That may be pretty difficult with a defense that is trying to avoid an eighth consecutive season below the league average, and an offense that has continued to regress with quarterback Derek Carr.

Would he actually turn down money if the Raiders aren’t good? Somehow I doubt it.

3. Khalil Macks don’t grow on trees

The quote: From a press conference after a September practice, via The Mercury News:

“It’s hard to find a great [pass rusher]. It’s hard to find a good one.”

The context: This is the first of the quotes about Mack on this list, which — spoiler alert — sweep all the top spots, because whew they’re all so good.

Gruden’s right. Pass rushers are hard to find. There’s typically 15 to 20 or so players who finish with double-digit sacks in any given season, and teams spend early draft picks annually to try to find one.

It’s right up there with quarterback as the most difficult position to land a good player at.

But the reason the quote is funny is that the Raiders had Khalil Mack, arguably the most dangerous edge rusher in the NFL, and traded him away to the Chicago Bears due to contract demands. Now the team is left with severe issues at pass rush and, guess what, they’re hard to fix.

2. Khalil Mack didn’t want to be in Oakland

The quote: From an interview with ESPN prior to the Raiders’ regular season opener against the Rams:

“Obviously, Khalil Mack didn’t want to play here. That’s what’s being missed here. He was under contract, he never showed up for an OTA, he never showed up for training camp, and it was obvious he wasn’t going to show up for the season. So don’t forget that. We have to get ready to play and I want players who want to be here, want to help us put this thing back in high gear.”

The context: Mack was entering the final year of his rookie contract this season, and opted to hold out in an effort to receive a contract that better reflected the fact that he’s as dominant a defensive force as there is in the NFL.

So, yes, he didn’t show up for OTAs or training camp, and he likely wasn’t going to show up for the regular season. But that doesn’t mean he was avoiding a member of the Raiders just like it didn’t mean Aaron Donald was trying not to be a member of the Rams when he held out too.

Donald also held out of OTAs and training camp, but received a six-year, $135 million deal at the end of August and now he’s back to wrecking shop in the middle of the Rams defensive line.

Mack wasn’t begging to leave Oakland, he was asking for a premium contract. One the Bears were willing to give and now it’s Chicago that’s reaping the benefits.

1. A bad pass rush hasn’t raised trade regrets

The quote: From a press conference in September, one day after the Raiders fell to 0-2 with a loss to the Broncos. Via East Bay Times:

“No, it doesn’t make me regret making the decision. We made the trade. We made the trade. There’s going to be hindsight, 50/50, all that stuff. We would have loved to have had him here, but he’s not here.”

The context: This is the top quote because “hindsight, 50/50, all that stuff” is just wonderful.

The saying, in most cases, is that hindsight is 20/20, meaning it’s easy to second guess a decision after you’ve seen the consequences. And since 20/20 vision just means you can see 20 feet as well as someone with normal vision can see 20 feet, I suppose 50/50 would essentially be the same thing.

But it also kind of sounds like he has some regrets, even though he’s telling the world he doesn’t. That was hammered home when Mike Silver wrote an article about Gruden that included a anecdote of the coach scrolling through his phone before a game to see what Mack did for the Bears that day.

Gruden at least understands why Mack dominating is a bad look:

To Gruden’s credit, he’s not oblivious: As Mack, the edge rusher he traded to the Chicago Bears shortly before the start of the regular season following a protracted contract dispute, continued his reign of terror against opposing quarterbacks -- forcing a pair of turnovers in the Bears’ blowout victory over the Tampa Bay Buccaneers -- Gruden knew it would turn up the pressure on him to win over an already-restless Raider Nation.

It’s too late now to do anything about it, so Gruden just has to accept it and move on. Getting Raiders players to move on might be a little tougher, though.

Like Gruden said — hindsight is clear — and the Raiders’ anemic pass rush has to make the team wish they had a Defensive Player of the Year level rusher coming off the edge.

Through the first two weeks of the season, Mack had better stats than the entire Raiders defense:

Hindsight is crystal clear on this one.