For 15 years the Pittsburgh Pirates have lost. For 15 year they change managers without changing the system that is wrong. Albert Einstein said Insanity is doing the same thing over and over again and expecting different results. The Pirates have been and continue to do more of the same. They can complain that they are not a big market team, and do not have enough money all they want, it's just an excuse. The Pirates don't try to build a team. The last several big signings in Pittsburgh were Brian Giles and Jason Kendall, both of whom were traded the following season to get rid of their contracts.
In order to be a winning organization, that has to be the goal of the organization from top to bottom. From what I've seen that's not the case here. Pittsburgh is solely looking to make money. The more of it the better. A few years ago they had a payroll of only 32 million, at the same time they made 35 million from revenue sharing in the league. That means that without a single fan showing up they would have still had 3 million profit.
What the Pirates really need to do is to stop looking at the money and look at building a team. It won't happen in 2 years, it will probably take at least 5. They need to have good draft picks that develop well, and good rule 5 pickups that make the team. Then they need to pick up very serviceable free agents for a decent price. The Marlins have proven that you don't need to have players that were known as marquee players before starting on your team in order to win it all. It is possible to build an organization from the inside out. They need to resign themselves to losing for the next year or two more while those young prospects develop, and they need to pay them to keep them there when they do. They need to make sure to keep Jason Bay and Jack Wilson and find a hitting coach that can bring Adam LaRoche out of his hitting slump, he was great in Atlanta. At the very least they can be like Tampa Bay and be exciting while losing games while they continue to build their club from bottom to top.