Derwin James Gets Paid Again, But the Chargers Still Haven't Learned How to Build Around Their Stars

Here we go again. Derwin James just became the highest-paid safety in the NFL for the second time in his career, and the Los Angeles Chargers just made another massive financial commitment that proves they are fundamentally broken as an organization. Do not misunderstand me. James is a phenomenal player. He is versatile, instinctive, and when healthy, he plays at an All-Pro level. The problem is not James. The problem is that the Chargers have constructed a roster so poorly that paying their star safety historic money is the exact opposite of what they should be doing right now.

Let me be clear about something first. I am not going to sit here and tell you that Derwin James is not worth elite money. That would be silly. He has proven he belongs in the conversation with the best safeties in football. His ability to play multiple positions, his range, his instincts in coverage, his willingness to come downhill and be physical, these are all elite traits. When James is on the field and healthy, he makes the Chargers defense significantly better. He is a rare talent at his position. The extension he signed is not bad because James is not good. The extension is bad because the Chargers organization has no business tying up this kind of money in any single defensive player given their current situation.

Look at the Chargers roster right now. They have Justin Herbert at quarterback, and he is a franchise-caliber talent. That is fantastic. They just committed massive money to him, which is exactly what you do with a quarterback who can be your guy for the next ten years. But here is where the Chargers have completely lost the plot. They have Herbert, and they have built around him with what exactly? They have an offensive line that is not good enough. They have one reliable receiving target in Keenan Allen, and Allen is aging. They have a running back committee that has not produced at elite levels. They have defensive holes everywhere that matter. The safety position is important, yes, but it is not more important than fixing the offensive line or finding another legitimate receiver to pair with Herbert.

The Chargers are operating under a complete misunderstanding of what it takes to win in the modern NFL. You cannot pay your safety like he is a quarterback. You cannot pay your safety like he is your best offensive lineman. You cannot pay your safety like he is your number one receiver. Those are the positions that actually determine whether you win or lose football games. A safety, no matter how good, cannot overcome the fundamental offensive deficiencies that the Chargers have. Derwin James, as great as he is, cannot make the offensive line better. He cannot throw touchdowns. He cannot catch passes. He cannot run the football. All he can do is play defense, and no single defensive player, not even an elite one, is going to make up for getting outmuscled in the trenches on offense week after week.

I have watched the Chargers for years now, and this is their pattern. They get a star player. They pay the star player. The star player plays well. The team still loses because they have not built the complete roster that is necessary to win. It happened with Antonio Gates. It happened with Ladainian Tomlinson. It happened with Philip Rivers. Now it is happening with Justin Herbert and Derwin James. The franchise has a chronic inability to use its draft capital and cap space in a way that creates a winning roster. They chase individual talent instead of building team football. That is a losing strategy.

The timing of this extension is particularly frustrating. The Chargers could have let James play out another year or two while they used their financial flexibility to address the offensive line, to add another pass catcher, to build out their defensive front. Instead, they have locked James in long-term at the highest safety salary in football. Now they have Herbert locked in at quarterback money. Now they have less flexibility to fix the things that actually matter. This is not complicated. You build from the outside in. You protect your quarterback with great linemen. You give your quarterback weapons. You build your defense around those fundamentals. The Chargers have decided to do everything backwards.

What makes this even more maddening is that safety is the one position where the draft has provided consistent value in recent years. There are always quality safeties available in the middle rounds. There are always safeties who can play at a high level without crippling your cap sheet. The Chargers did not have to make Derwin James the highest-paid safety in the league to keep him happy. They could have offered him very good money, kept him on the team, and used the money they just committed to him over the next four years to build an actual contender around Justin Herbert. Instead, they have essentially tied one hand behind their own back.

Here is the reality that the Chargers organization needs to understand. Derwin James is not going to get them to the Super Bowl. Justin Herbert is not going to get them to the Super Bowl by himself either. A complete roster will get them to the Super Bowl. A team that is strong in the trenches, that has multiple receiving options, that can run the football, and that has a solid defense will get them there. Individual stars, no matter how talented, are not enough. The Chargers have the quarterback. That is the hardest thing to find. Now they need to build around him intelligently. Paying Derwin James the most money any safety has ever made is not intelligent. It is reactive. It is short-sighted. It is the exact kind of move that keeps a franchise stuck in mediocrity.

The NFC West and AFC West are both loaded with good teams. The Chargers cannot afford to waste resources. They cannot afford to make moves that make them feel good in the moment but cripple them financially down the road. Yet that is exactly what this extension represents. It is a feel-good move for the front office. It is a way to tell the fan base that they are doing something. But it is not the right move. The right move would have been harder. It would have meant telling James to take a good deal but not the highest deal. It would have meant using that money to get an elite right tackle or another legitimate number two receiver. It would have meant thinking about the team instead of the individual star.

I am going to be proven right about this. In three years, the Chargers will be a middling team in their division. They will have a Hall of Fame quarterback stuck with an incomplete roster around him. They will have an elite safety who cannot cover for the deficiencies elsewhere. And the front office will probably make another big money move to try to fix it, doubling down on their failed strategy. This is the Chargers cycle. They are incapable of breaking it.

Derwin James deserves to be paid well. He has earned it on the field. But the Chargers organization deserves criticism for how they have handled their cap space and roster construction. They have made James the highest-paid safety in the NFL for the second time. That tells you everything you need to know about their priorities and their understanding of how to build a championship team. It is not about individual stars. It is about complete rosters. The Chargers keep forgetting that lesson.

VERDICT: This extension is a mistake. Not because Derwin James is not good. Because the Chargers do not know how to build around their good players. They will regret this deal in the same way they regret every other big money decision they have made in the last decade. The franchise is fundamentally broken in how it approaches roster construction. Paying your safety the most money in NFL history does not fix that. It makes it worse.