When will this organization be in position to win? Which players will still be around? Is there really a plan? What is there left to offer fans in the present? And most importantly: When will this revolving-door finally stop revolving?
To that, general manager Neal Huntington had this: "We're getting closer. We've worked very hard to stop the cycle of losing, and with that stops the cycle of trading. This is the group that we're going to build around.
"This is the group that we're going to build around. We've got some ability to add to it via free agency this offseason in the right situation. But this is the group we're going forward with."
That is Huntington's message of accountability to fans. It's also essentially the same message that Huntington delivered to the 25 players in the Pirates' clubhouse on Friday.
Huntington's two-year mark with the organization won't hit until late September, but his marks on the franchise are reminiscent of someone whose tenure has been much longer. Only five players -- Matt Capps, Zach Duke, Paul Maholm, Ryan Doumit and Steve Pearce -- who were on the Major League roster have remained Pirates since Huntington was named the successor to Dave Littlefield. And in fact, only another two -- Jesse Chavez and Andrew McCutchen -- were even in the organization.
Of the other 18 players, 11 were acquired via trades Huntington made, two came from the Rule 5 Draft, one came off the waiver wire and four were signed as offseason free agents.
That's a stunningly quick pace for turnover. But as manager John Russell explained during last week's whirlwind of activity, he and Huntington concluded right away that Pittsburgh had no way around such immediate and drastic turnover if there was any hope of becoming a perennial contender.
"Neal and I sat down in his office a couple weeks after I was hired and started going over things," recounted Russell. "The first thing we went over was the depth chart. It wasn't pretty. We knew going in that to make ourselves a competitive organization that we were going to have to develop more players, we needed better players in our system.
"You look at what Neal has done today, it's not the most popular moves. You look at the depth. You look at the quality of players we have here. You look at the quality of players we have in the Minor Leagues now. I think our organization has turned over rather quickly and in a positive direction."
Huntington, too, spoke of those initial organizational assessments in 2007.
"We knew coming in that we needed to do two things," Huntington said. "We needed first and foremost to change the culture. That doesn't necessarily mean you need to turn over the entire roster, but we needed to change the culture here, both on the field and off the field in terms of our development staff, in terms of our scouting, in terms of our Major League staff, in terms of our approach as the organization. We put a significant amount of our resources into our infrastructure and our personnel and we knew that needed to happen.
"We also knew that we needed to be deep in our talent pool. For us to win, we needed deeper talent in our system. We went into last year with the intention of giving that club every chance in the world to dictate the moves. We weren't competitive. We were double-digits out at the Trade Deadline. We came into the season again, wanting to see what this team could do. Unfortunately, we were not competitive and not where we wanted to be."
So where do the Pirates stand after all that has transpired this summer? In an eight-week span, 10 players with notable big league experience in Pittsburgh were dealt, beginning with Nate McLouth on June 3 and concluding with Tom Gorzelanny and John Grabow going to the Cubs on July 30. In return, the Pirates netted 17 players.
Five of those players have already joined the big league club. Charlie Morton, acquired from the Braves, has been a fixture in the rotation, while former Cub Kevin Hart is two days from joining him there.
Lastings Milledge, formerly of the Nationals and Mets, is now an everyday outfielder. Former Mariner Ronny Cedeno is the team's shortstop. And Joel Hanrahan, also sent over from Washington, is being groomed for a late-inning role out of the 'pen.
"People now might wonder what we're doing, but if you keep looking at all the names we're getting and all the premier talent we're getting, it's going to equate to a very solid, very good ballclub in Pittsburgh," Russell said. "Neal has made it public, I don't know how many times, that we're not in to win this for one year. Our goal is not to get to .500. It's to have a championship-caliber team. We have big names all over the diamond. That's where we're headed."
A number of those big names are still in the Minors: third baseman Pedro Alvarez (No.2 overall selection in the 2008 First-Year Player Draft), outfielder Jose Tabata (acquired from Yankees in a July 2008 trade), outfielder Gorkys Hernandez (acquired from Braves in a June 2009 deal), Tim Alderson (acquired from San Francisco in a July 2009 trade) and Jeff Clement (acquired from Seattle in a July 2009 deal).
It's not unfeasible that all five of those players could be ready to make their debuts in Pittsburgh by the end of 2010.
The caliber of the prospects is further supported by Baseball America's annual preseason rankings. With these trades now in the rearview mirror, the Pirates have five of the publication's top 75 prospects as ranked at the start of the 2009 season: Alvarez (No. 12), McCutchen (No. 33), Alderson (No. 45), Hernandez (No. 62) and Tabata (No. 75).
All this translates to competition for those Major League spots, something that even those who have opposed the coming and going of players can agree wasn't present in the organization before Huntington's arrival. It took saying goodbye to fan favorites to ensure at least adequate depth.
Now that depth will breed competition, and that, Huntington believes, will in turn breed success.
"Every one of those guys has a tremendous opportunity to step forward and become a Major League player and to stranglehold a job that's there for years to come," Huntington said. "If they don't do it, we've got people coming behind them in the Minor League system. The days of scholarship are over. The days of just graduating players to the Major Leagues are over, giving guys jobs, it's over."