Not only did Jon Gruden bring shame to the Raiders over his repugnant emails -- but he also oversaw a decline in overall talent and left the team in a worse position long-term after his three-plus years at the helm of the organization.
This according to football analyst Bill Barnwell of ESPN, who took a detailed look at Gruden's moves as the team's top-ranking decision-maker in football operations since 2018 in a recent Insider piece (paywall).
During his four-year second stint with the Raiders, Gruden sold off star players for "pennies on the dollar," routinely reached for borderline prospects with the precious draft picks they acquired in exchange for said players, and seemed to make a habit of cutting veteran players not long after acquiring them in trades or via signing, Barnwell writes.
Gruden did manage to have above-average offenses, in part by resurrecting the career of quarterback Derek Carr and unearthing star tight end Darren Waller from the Ravens' practice squad, Barnwell concedes.
But the rest of Gruden's work with the Raiders was underwhelming -- not unlike much of his time in Tampa, where, according to Barnwell, Gruden won a Super Bowl mostly because he inherited a ready-made winner from predecessor Tony Dungy.
Meanwhile Gruden's pivotal trades of Raiders linebacker Khalil Mack and wide receiver Amari Cooper brought back several draft high draft picks, but they did not yield players of Mack's or Cooper's ability.
The Raiders lavished a hefty $100 million contract on Gruden after years of mediocrity, in hopes that he might restore them to relevance. Instead, he brought shame on the team and himself.