In 2016, the Oakland Raiders were finally back. After 14 years without a winning record, the Silver and Black went 12-4 and returned to the playoffs for the first time since losing to Tampa Bay in the Super Bowl. This was a team on the rise. They had a young stud at quarterback. They had a defensive player of the year. They had a brash coach who was unafraid to gamble with the game on the line. It seemed like the Raiders were once again in the mix to compete for a championship.

That 2016 season ended in bitter disappointment. Third-year quarterback Derek Carr suffered a season-ending injury in week 16. The Raiders lost their final regular season game with rookie Connor Cook under center. That loss cost Oakland the division and a first-round bye in the playoffs. Instead, the Raiders had to travel to Houston to play against the vaunted Texans defense in the Wild Card round. Cook struggled mightily in the game and the Raiders lost 27-14, ending their season.

Many felt that had Carr stayed healthy, that team could have made a deep run in the postseason. After all, Oakland had seven Pro Bowlers and three players named to the AP All-Pro team. Still, despite the abrupt end to the season, it seemed like the Raiders were poised for another great season in 2017.

That great season never came. Oakland struggled through the 2017 season, facing a much tougher schedule. The 2016 Raiders had the 15th hardest schedule in the league. The 2017 Raiders had the fourth. Injuries limited the team as offensive tackle Donald Penn finished the season on IR. So did Oakland’s first two picks in the 2017 draft. Oakland still had bright spots. Khalil Mack dominated, becoming the first player ever to be named first-team All-Pro at two different positions in the same season.

However, in addition to the tougher schedule, there are some easy things to point to as the reason for regression. The offense fell off a cliff. The Raiders gained 50 fewer yards of offense per game and scored eight fewer points per contest. Not exactly a recipe for success. Oakland also went from the top team in turnover ratio in 2016 to tied for 29th in 2017. That was a swing over 30 possessions, roughly two per game. That could help explain some of the scoring and yardage difference.

After a 6-6 start, the Raiders finished the season on a four-game losing streak. That cost Jack Del Rio his job as the head coach. Little did we know, he would be the first of many crucial pieces to leave Oakland.

It ended up being a tumultuous offseason for the Raiders. During the 2017 season, the team announced it would be moving to Las Vegas for the 2020 season. The fan base was already unsettled as a result. Then the Raiders signed Jon Gruden to a massive deal, reportedly worth about $100 million over 10 years.

Here’s the thing, Gruden hasn’t coached a football team in 10 years. His last gig was as the Buccaneers coach from 2002 to 2008. He did win a Super Bowl during that first season, beating none other than the Oakland Raiders.

The move made a lot of sense from the story perspective. Gruden had been the head coach of the Raiders 1998 to 2001, only to be forced out by former Raiders owner Al Davis. Gruden has said he feels like there is a lot that he would like to do to finish his legacy in Oakland.

When you pay a coach that much money though, it makes it really difficult to explain to your players that you can’t pay them. The team elected to extend Derek Carr’s contract with a lucrative deal that was the richest in NFL history for a short period of time. It seemed like the logical move, until the consequences quickly followed.

Khalil Mack is one of the best defensive players in NFL history, yet the Raiders did not pay him. Mack held out all summer long in hopes of landing a new contract. It never came, at least not from Oakland. Just before the start of the season, Gruden shipped Mack to Chicago for a package of draft picks. Mack has been a beast through the first four weeks of the NFL season. He is tied for second in the league with five sacks. He also leads the league with four forced fumbles alongside J.J. Watt, and has an interception.

The loss of Mack leaves the Raiders seemingly in a rebuild mode. Oakland has started the season 1-3 and shows no signs of turning it around. It needed overtime and a bit of assistance from the officials to pull off the victory and avoid what would have been a truly terrible start to 2018. The Raiders have scored the fifth fewest points this season. Apparently, Gruden does not really know how to rebuild either.

Thinking about it, it’s not too shocking considering this is a franchise known for the mantra “Just Win Baby.” The Raiders were never good at rebuilding. They struggled to do so for the aforementioned 14 years without a winning record. Oakland failed to draft well or attract free agents to help turn the franchise around. The environment for this Raiders franchise has been toxic for years. Even when it did bring in top-tier talent, like Randy Moss or Charles Woodson for the second time, it couldn’t convert that into true success. Looking at this Raiders team now, one that is going to require a ton of roster turnover and a general talent overhaul, Gruden has not positioned himself to rebuild in the coming years.

Oakland has the oldest roster in the NFL. The Raiders on average are 27.32 years old, according to Spotrac. The next youngest team is the Atlanta Falcons at 27. Oakland is more than a full year older than the league average. It also has the most players signed over the age of 30. Gruden has built a team ready to win this season, but it will come nowhere close to even making it to the playoffs. Gruden is also burying Marquel Lee and Karl Joseph, young players with bright futures, on the depth chart.

At this point just two years ago. The Raiders were 3-1 and seemed like a team destined to compete for the next several years. Today, this team is years away from competing. Gruden has one hell of a task ahead of him and this organization has some explaining to do as to how quickly it let the team fall into turmoil.