There are a few sports franchises that can be categorized as a comedy of errors. One of them is certainly the Oakland Raiders, and they did themselves no favors by hiring Jon Gruden to a 10-year contract, as well as the ensuing debacle that he alone caused. Trading the NFL’s best defensive player in Khalil Mack has done nothing but cause Gruden serious regret, but now that the Raiders are struggling mightily, it’s time to ask the question of how long he’ll stay with the team.
Let’s consider the fact that he’s owed $10 million over the next nine years (he’s already received the payment for this year) and understand that the Raiders aren’t going to give up on him immediately. Also, he did get a nice return from the Chicago Bears in the form of draft picks. History tells us that there’s a greater likelihood of success with draft picks, so Gruden will have to pick well in order to make those pan out.
The real concern with Gruden is that the Raiders are god-awful through only 5 weeks of his first season. While he’ll obviously be given the benefit of the doubt after this year, his leash will be much shorter next year, and if he fails to deliver better results in 2019, it may be his last. Whether he gets his contract bought out depends on how badly Raiders owner Mark Davis wants the team to succeed.