I think, to me, we are at a point in NFL history where there is absolutely no team older than 25 years that has absolutely nothing to show for it.
It then just becomes opinions on whose achievements weigh less due to overall weight of what success they had, how long ago it was, etc.
I prefer to weight most for time since the last even decent success. When the losing goes on and on, especially when it is only punctuated by brief success is what stings the most to me.
Lions- it has to be this to me. Yeah, they won championships 60+ years ago. But that just really doesn’t matter now. With the exception of a lot of hope never fully fulfilled in the 90s it has been pretty abysmal season to season.
Chargers- no one is remembering that sole championship in 1963 (probably not an exact moment in time most people were fully absorbing sports championships, anyways). The few highs they’ve had since (early 80s, 90s, LT years) have been short lived and ultimately not fulfilling.
Browns- Yes, initially on coming into the league, and again in the 60s they were dynastic. But, since then the few highs ended in crushing blows. Then, for the fans to lose the team, and get back something that looks, but maybe doesn’t feel the same. Then....the last 25 years. Painful
(Honorable mention)....Bills- I have to. Yeah...the late 80s/early 90s teams were scary fucking good. But, the four straight crushers in the SB still merits pain. And what followed the next 25 years increases the pain more. They are doing well right now, and they deserve some vindicating success ASAP.