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Losing Khalil Mack would become Jon Gruden’s legacy, putting permanent dark cloud over his Raiders return

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Details of the current state of the negotiations between the Raiders and Khalil Mack paint a bleak picture. And it’s in Gruden’s hands to make it right. Or forever live with the consequences.

NFL: Green Bay Packers at Oakland Raiders Cary Edmondson-USA TODAY Sports

Panic mode is setting in. The season is fast approaching and the reports from both sides of Khalil Mack’s contract negotiations are not promising. Specifically that there aren’t any negotiations happening.

A report Monday night from Charles Robinson of Yahoo! Sports paints a bleak picture of the contract standoff between Mack’s people and the Raiders. Here are the details that stand out:

1. The impasse is likely to last into the season.

2. Negotiations have been at a stalemate since February (we’ve heard this before).

3. The situation has devolved into a “pay him or trade him” conversation.

4. Jon Gruden has final say on any deal that gets done.

5. Gruden is open to trade offers.

6. Funding for Mack’s contract is not an issue for Mark Davis.

7. The Aaron Donald deal is not a holdup.

8. Mark Davis may need to step in.

9. The team is ok with Mack coming back and playing unhappy.

None of this is good news. Gruden knows this.

It can’t be understated how much of a mistake botching this would be for Jon Gruden’s legacy. He hasn’t even coached his first game back with the Raiders and he is already in serious danger of raining on his own parade by taking the field without the best defensive player in the NFL.

How long has this franchise been waiting to actually draft a player the caliber of Khalil Mack? Have they ever drafted a defender of his talent level? That’s debatable.

They’ve only ever drafted one other player who went on to be named Defensive Player of the Year. That was Lester Hayes, who they selected in the 1977 draft and who won the award in 1980 with a still NFL modern-era record 13 interceptions. The only drafted Hall of Fame defender the Raiders have had is Howie Long.

Mack is already more accomplished than Hayes and is in the same conversation at Long. That 1980 season was Hayes’s only All Pro season. Long was named All Pro twice. Mack has already been named All Pro twice in four years, including being the only player in the history of the NFL to be named All Pro at two different positions (LB, DE) in the same year.

Saying this would be like losing Howie Long in his prime doesn’t even cover it. Long came to the Raiders in their heyday. The Raiders had been an NFL powerhouse for nearly a decade when he started going to Pro Bowls. That team didn’t need a player like Long the way this team has needed, and will continue to need Mack.

This franchise hasn’t sniffed success since…well since they were fielding the team Gruden built in 2002. Since he beat them in the Super Bowl in his first season as head coach of the Buccaneers.

That Super Bowl loss sent the Raiders on a downward spiral from which they have yet to recover. And it was all because Al Davis traded Gruden for draft picks. It would seem Gruden would understand that trading proven commodities for draft picks is not such a great strategy.

Now for Gruden to come back and have his first act be to lose the greatest thing to happen to this team in 17 years? How would the two most lasting memories of Gruden for Raiders fans not be him TWICE ripping their hearts out?

And that is to say nothing of the immediately on-field ramifications of attempting to field a shaky defense wholly reliant upon the only solid piece to its foundation.

This is not how Gruden wants to get his 10-year, $100 million return to the sideline started. It’s a stain that will never wash off. Nor should it.

Get this contract done. Pay the NFL Defensive Player of the Year like he’s the best defensive player in the NFL. Don’t make your first step back into coaching be a permanent, unforgivable black mark.