All the woes of the Pittsburgh Pirates start at the very top. Where do I begin...?
1. Ownership chooses to pocket revenue-sharing money instead of reinvesting it into the team. Seems like Minnesota, Milwaukee, Oakland, and a few others do not have a problem doing the reinvesting thing.
2. The last impact player the Pirates have drafted was a fellow by the name of Barry Bonds...and that was 22 years ago! During the last 15 years, the Pirates have yet to draft anyone who can help the team at the major league level. Picking pitchers most of the time (remember Bobby Bradley in 1999, Clint Johnston in 1998, Kris Benson in 1996, Bryan Bullington in 2002, etc.) or hitters who never seem to hit (J.J. Davis in 1997, Mark Farris in 1994, Chad Hermansen in 1995, etc.) sure as hell doesn't help, either. The best trades in the last 15 years have involved the same player: Brian Giles. Giles was picked up in 1998 for Ricardo Rincon and in 2003, was shipped to San Diego for Oliver Perez, Cory Stewart, and Jason Bay. That's it.
3. Not utilizing free agency has killed the Pirates. When was the last time they signed a free agent that has actually worked out? We have to go back to 1999, when they picked up Ed Sprague (who was their All-Star game rep that season). Every year, Pirates management tries to sell the fan base on "improving", only to bring in guys like Pat Meares, Derek Bell, Mike Fetters, Matt Morris, Victor Santos, Brant Brown, Jose Hernandez, Raul Mondesi, and the list goes on and on. Trading away useful players hasn't helped much as well. Losing Aramis Ramirez, Kenny Lofton, Oliver Perez, Chris Young, among others has just been too painful to watch.
4. Fleecing local government to pay for a new stadium. Current ownership PROMISED the fanbase that they would put a better product on the field if the city would fund a new ballpark. City caved, knowing quite well that a franchise over 100 years old simply cannot be forced to move away. Ownership has not lived up to their end of the bargain, annually cheating the fans out of decent baseball. The endless promises to get better fall upon deaf ears.
5. This team is horribly mismanaged from the top on down. There needs to be a complete overhaul. Starting in the front office, where David Littlefield clearly doesn't know what the heck he's doing. he is making moves trying to save his hide. Jim Tracy deserves better, but he has to go as well. To me, Tracy is managing scared. The everyday lineup has more holes than O.J.'s alibi. Somehow, Jason Bay has horribly regressed. New front office, new manager, new core of talent, new scouts, hell, maybe even a new logo. Clean this mess up!
To answer your question: if these issues are addressed carefully and dilligently, they will win again.
Lifelong Pittsburgh Pirates fan (been suffering since 1980)!