The San Diego Chargers It's hard to say what's more remarkable...the fact that, in this day and age, the San Diego Chargers have reached the postseason five of the past six years, or the fact that they have failed to reach the Super Bowl in those five years. The Chargers are a perennial title contender. In each of those five playoff years, they’ve either won a postseason game or finished with 12-plus wins in the regular season. You rarely see this kind of sustained success in the NFL these days. Reason being, you rarely see owners and front offices put up with this kind of sustained failure.