perennial loser

Perennial losers are people who suck basically all the time. They don't realize they suck because they often delude themselves by clinging to some distant past event to justify their existence.

Dodger fan: "I'm cool because we won all these world series way back in the day." Reality: You're payroll equals the rest of your division combined and you can't even win that consitently. You are a perennial loser.