Management and the front office does have something to do with it, but yes, Pittsburgh is a small-market baseball city. Large market for football, small market for Baseball. (Similar to Los Angeles being a great market for Basketball and Baseball, but having a very small share for football). Small markets tend to have low revenue coming in, so they can't really pay to get big or established free-agents. Couple this with a front office that cannot draft or develop prospects and you have a cesspool of mediocrity.

Because they are in a small market and have a small payroll. Other teams have made this work (Oakland, Minnesota), so Pittsburgh really doesn't have an excuse any longer. They need to farm some talent.

EDIT: Yes Sugardaddy Sean, Pittsburgh is a very small market. Only 3 teams have smaller markets according to the below source. Just because the Steelers have strong support doesn't mean the market is large. Look at the Green Bay Packers. I live in Nashville with the Tennessee Titans, and there's no way we could support a MLB team with 162 games a year.

Pittsburgh a small market? Are you kidding me? A city that is home of the Steelers? Ya right small market haha

Let me tell you the real reason, its because their managment is horrible. They are a cursed franchise they had Barry Bonds and got rid of him. They have a cheap owner who doesnt spend money on free agents. They traded away Aramis Ramirez their best prospect a number of years ago and give bad contracts to bad players. If they want to get over .500 the firs thing they need to do is get rid of their owner or general manager because the way they draft and spend they will never break this 17 straight seasons without a winning season streak. Sad truth

Because they have bad coaching, lame fan support and in general just mostly bad players

Poor ownership.

cause they're from pittsburgh,,hahahaha

I blame the whole of Pennsylvania..*cough* Phillies aren't better off