Jon Gruden’s $100 million contract and head-scratching offseason moves mean the pressure’s on

There’s pressure that comes with a huge paycheck. The 10-year, $100 million contract given to Jon Gruden by the Raiders likely means his job security won’t come into question any time soon, but it also means he’s under the microscope.

That’s a whole lot of money for a coach who’s 10 years removed from coaching.

There’s reason to be optimistic that Gruden’s time as a Monday Night Football commentator and analyst allowed him to learn, evolve, and better understand how to lead a team. But it’s also worth remembering that in the six seasons after he coached the Buccaneers to a Super Bowl victory, he compiled a 45-51 regular season record and 0-2 mark in the playoffs.

Gruden was facing the weight of expectations the day he took the job, but his first eight months in Oakland have only ramped up the pressure.

Trading Khalil Mack casts quite a shadow

Near the end of August — and just a few days before Mack was sent to the Chicago Bears — SB Nation’s Raiders blog, Silver and Black Pride, summed up the gravity of a possible trade:

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.

The Raiders received a couple first-round picks, a third-round pick, and a sixth-round pick in the trade, and gave the Bears a second-round pick along with Mack.

In Mack’s first game with Chicago, he only made the Raiders look worse by debuting with one of the most dominant defensive halves ever. In a primetime game against the Packers with the football world watching, Mack became the first player since 1982 with a sack, interception, touchdown, forced fumble, and fumble recovery in a half.

The sticking point for the Raiders was the huge contract Mack was asking for, and received from the Bears on the same day he was traded. According to Gruden, Mack’s holdout for more money proved that he wasn’t a dedicated enough member of the Raiders.

Mack was arguably the only solid piece of foundation for a defense that has struggled in recent seasons. Without Mack, it stands to take another step in the wrong direction and Gruden will only face more criticism if the Bears’ new pass rusher continues to excel.

Mack wasn’t the only puzzling decision

Gruden is a character. He’s an entertaining personality who spent the first few months of his return to the Raiders talking about his love of old school football and fullbacks. One player said he’s been showing the team game tape from decades ago:

It hasn’t all been bad. The Raiders made much-needed changes in the secondary and addressed the defensive line in the 2018 NFL Draft. But there’s a growing list of head-scratching moves the team has made since Gruden’s arrival:

• Signed 33-year-old former Packers receiver Jordy Nelson to a two-year, $15 million contract instead of keeping 31-year-old receiver Michael Crabtree, who signed a three-year, $21 million deal with the Ravens.
• Traded receiver and kick returner Cordarrelle Patterson to the Patriots along with a sixth-round pick to get a fifth-round pick.
• Traded a third-round pick to the Steelers for Martavis Bryant, who was cut by the Raiders after preseason.
• Traded a fifth-round pick to acquire AJ McCarron, who fell out of favor in Buffalo after losing a quarterback battle with Nathan Peterman and Josh Allen. Peterman finished Week 1 with two interceptions and a 0.0 passer rating.
• Signed Doug Martin in free agency after he averaged fewer than 3.0 yards per carry in each of the last two seasons with the Buccaneers.

Technically, the man in charge of the roster is still general manager Reggie McKenzie. But it’s clear that Gruden’s the one at the center of the team’s future.

“Jon’s the head coach and he’s going to be here a while, so it’s important that he gets the players he wants and builds a team he wants to build,” Raiders owner Mark Davis said in March, via NBC Sports Bay Area. “Reggie is there with his staff to find the players, and also to keep the (salary) cap and everything else in order.”

The buck is going to stop with Gruden. His gigantic contract means he can’t escape the heat and the Raiders’ questionable roster building has dialed up the pressure even further.