Statistically, I’m pretty sure that spending a ton of money on your best player is the road to ruin for every single team.
I get it, if you’re The Man, you want to be paid better than everyone else. Instead of just “rich beyond the dreams of 99% of people in the country for the rest of your life” you want to be rich beyond the dreams of even most of the rich people in the country and why not get it? But let’s end the foolish “wanted to be a Raider For Life” and “go team” blathering afterwards because you know you’ve just crippled the team and have likely permanently reduced your chances of success.
Tom Brady never had to be the highest paid player on the Patriots. (neither did plenty of the rest of the team). They have been rather successful for a long time with remarkable consistency. Tom Brady is still going to be a very rich man until the end of his days. When a player decides that he needs to make as much money as possible, it takes away from the rest of the team and if your goal was to win, you played yourself. History’s pretty clear on this for the most part. Does the team have to do it? Yeah, probably. Does the player have to demand it? Eh… not really. Luckily the Raiders won’t have any real expectations for winning with such a solid, loyal fanbase.