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1.
A once proud institution who pisses away a loyal following with obviously bad, money-influenced decisions.

The thrift store for all other major league baseball teams.

A monetary drain upon a city that keeps asking for more and more while continuing to offer less and less. Akin to flushing one's money down a toilet.

The response to the question: can a professional baseball team both suck and blow at the same time?

Complete embarassment.
Baseball Exec: Darn, I just lost my catcher for a season due to his thrid drug scandal, what should I do?
Assistant: I'll call the Pittsburgh Pirates and get their starting catcher. I have a used Plymouth I know they'll take for him.

Mayor: I don't understand what happened to all of the city's revenue?
Staff member: I believe we've been Pittsburgh Pirated, sir.

Wow, last night I drank so much that I urinated in my pants, cried like a baby for hours, and then I left the bar. I think a made a complete Pittsburgh Pirate out of myself.
by Fraud Exposer June 26, 2009
 
2.
A violent sexual act involving the thrusting of a an erect penis into a partner's open eye followed by kicking said partner's leg in a manner severe enough to cause significant pain and/or damage, temporarily giving them the appearance of a one-eyed, peg-legged pirate.
Things were going great with Emily until I gave her a Pittsburgh Pirate. Apparently most chicks aren't willing to lose the use of their limbs or eyes for the sake of unparalleled eroticism and unprecedented sexual gratification. Women.
by Hubert Cumberdale Jr. May 11, 2009