I couldn't think of a better title for this post, but stick with me. I want to analyze this situation from the two available, meaningful points of view.
Should Antonio Gates re-sign with the Chargers?
Let's start here. Antonio Gates seemingly wants to play another season. His main reason seems to be that he doesn't want to go out as the starting TE on a 3-13 team that ranks among the worst in team history.
Before we get into if the team will or should offer the big guy a contract, I think it's fair to ask if Gates should consider finishing his career elsewhere.
If winning next year is what is important to Gates, there are much better options out there than the Chargers, and Gates will be free to sign with any of them as an unrestricted free agent. Signing with the Packers, for instance, all but guarantees him a winning season and gets him closer to his hometown of Detroit.
It's worth mentioning here that Antonio Gates may not want to play for the "Los Angeles Chargers", and that may be his only option if he wants to stay with the same franchise. Gates has no ties to Los Angeles, or the fanbase up there, and therefore has less reason to want to sign with them.
Should the Chargers re-sign Antonio Gates?
Let's get into opportunities and options. By DVOA and DYAR, Antonio Gates falls into the top-half of the NFL's starting Tight Ends. At 35 years old, he has been able to regularly get open against LBs and DBs, and that makes him attractive to many NFL teams.
The Chargers will be one of those teams, no doubt, but they're in a bit of a predicament at the TE situation. By now they were supposed to be transitioning to Ladarius Green as the team's starting TE. However, Green only gets regular targets when Gates is out, and both guys are free agents. If the Chargers sign Gates, there's a good chance that Green won't be interested in signing with the team.
Tom Telesco has built a roster that spends a lot on veteran players but doesn't win games. The way to turn that team around and win games is not by continuing to shell out big money for those same veteran players to stick around, especially because veteran players are very expensive.
Antonio Gates is currently the 3rd highest-paid TE in the league. His cap hit this year is $8.3 million. Even if he drops to 10th highest-paid, his cap hit is still well over $6 million per year. (For comparison's sake, Ladarius Green's cap hit is less than $800,000 this season.)
Bringing Gates back to the team also means pressing reboot on the post-Gates TE plan for the team. If the Chargers can't re-sign Gates and Green (which they can't), that means that signing Gates would force the team to use one of it's higher draft picks on a TE that can take over whenever Gates' contract is up. Having that type of thing dictated to you, forcing you to use a draft pick on a backup when your team needs effective starters at other positions right now, seems like a bad plan.
Simply put, re-signing Antonio Gates doesn't make the Chargers better. In fact, it probably makes them worse in the short-term and the long-term. The only reason to sign him is to let him get every single record he can and to be able to say the Chargers were the only team he played for, but that becomes less of a big deal when you split the history by moving the team anyway.
If Antonio Gates wants to win, and the Chargers hope to do the same thing, it's probably best for the two to part ways and for the Chargers to usher in the beginning of the Ladarius Green era.