Joey Bosa will be entering his fifth season in the league with the Chargers after the team picked up his option in August. Even though he is under contract this season, the Chargers need to work on an extension for Bosa sooner rather than later.

Rookie Contract Negotiations

Fans will remember that Bosa and the Chargers had trouble negotiating a contract when he was a rookie. Rookie contracts are more or less straight forward now that there is a cap on how much each pick can make. This didn’t seem to matter, as Bosa ended up holding out to start his rookie season.

The issue wasn’t the amount of money, but rather the schedule of payment for his bonus and offset language in the contract. He compromised on the bonus payment schedule with some of the $17 million being deferred. Bosa ended up playing in 12 games as a rookie, but spent much of the preseason away from the team.

If the Chargers and Bosa had issues the first time around, it is within reason to think that a second contract will pose more problems. This time around, there will be no pay scale to fall back on. The Chargers and Bosa will have to agree to terms on money, bonus payment structure and offset language. There is also a possibility Bosa will want to test the free-agent market. To work through the negotiations and to prevent Bosa from holding out again in 2021, the Chargers should start working on a contract extension now.

The Team is Re-Tooling

While there is still plenty of talent on the roster, the Chargers could have a down season for a few reasons. First and foremost, Philip Rivers will not be with the team for the first time since 2004. With a new quarterback, whether it is a rookie or not, will take time to adjust. Rivers certainly wasn’t at his best last season, but the offense will likely still take a step back next season.

The Chargers have plenty of free agents, who could leave because they don’t want to wait for a new quarterback to establish himself. Melvin Gordon, Hunter Henry and Travis Benjamin could all walk this offseason. That would be a huge hit to the offense. There are some free agents on the defensive side of the ball as well, but the offense could have the majority of the losses.

If these free agents decide to leave when free agency hits, the team will have a hard time being successful in 2020 after going 5-11 last year with these players. What adds to the possibility of a rough season is that the Chargers have some of the worst injury luck in the league (Henry, Derwin James and countless others have been injured over the last few years, hurting the Chargers’ chances of competing). Getting a contract finished before Bosa sees what could be a rough team season is important. If they don’t play well in 2020 and he is an unrestricted free agent, he could elect to go to a better situation.

Rumors

The first set of rumors surrounds a Bosa holdout for this season, as mention by The Athletic. As seen this season with Jadeveon Clowney, a holdout can sometimes end with the player not ending up on their original team. Bosa could holdout and demand a trade if he isn’t happy with the current situation of the team.

There have already been rumors that Bosa might want to leave the Chargers in free agency next season. Reports have come out that he could want to go to San Francisco to play with his brother Nick, who had a very successful rookie season that saw his team go to the Super Bowl. These rumors are starting a year before he hits free agency and more will likely pop up over the season. In the NFL, where there is smoke, there is usually fire.

With the contract issues and the team needing to find a new quarterback, along with filling other holes on the roster, it isn’t inconceivable that Bosa will be tempted to leave and chase a ring. Whether he wants to go to the 49ers or another Super Bowl contender that will give him what he wants in a contract as well, it is very easy to see why Bosa would want to move on.

Conclusion

If the Chargers want to have the best shot at retaining Bosa for the future, they should start the negotiation process now, even if they have free agents that will hit the market in March. The longer that they don’t agree to terms just means it is more likely that a deal between the two parties won’t be reached.

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