Floyd: When Do the Pirates Draw a Line in the Sand?

With the trade deadline in the rear-view mirror—the Pirates sold, on par with much of the past three decades—the focus starts to turn to next season. Even with plenty of baseball left to play, that milestone represents pushing in the cards, kicking the can down the road in hopes of better luck next season, or the season after that. On and on it goes, ad infinitum.

When will the Pirates and general manager Ben Cherington finally turn the page, draw a line in the sand and stand pat or buy as the calendar flips to August? When does focusing on the big league club outweigh taking a flyer on a rookie ball prospect?

The Pirates brought in veteran leaders like Rich Hill and Carlos Santana for two main reasons. One was to help the team with their play on the field now: the other, to set an example for the next generation of players, show them how to carry themselves as professionals, teach them to win.

With a team full of rookies following a flurry of call-ups—more than half the current 26-man roster had less than one year of service time at the beginning of 2023—one might think that veteran presence is necessary now more than ever.

Instead, they’re gone for greener pastures, flipped for future prospects.

From the Horse’s Mouth

Cherington discussed the impact veteran players like Hill and Santana brought to the Pirates in his weekly radio appearance Sunday.

“We acquired them all this past offseason with the intent to get better,” Cherington said. “I do believe we got better in part because of their contributions both on the field and off the field.”

Manager Derek Shelton took it a step further when describing Hill’s contributions.

“He is emotionally attached to every pitch, and I think that’s a wonderful thing for young players to see because it shows how much he cares,” Shelton said. “Right from day one of spring training, just the voice and the ear for young pitchers in terms of listening to what they’re doing and watching how he goes about his day.”

With that impact in mind, why did the Pirates cast their veteran leadership structure aside? Why would they prioritize the potential development of future prospects over the tangible development taking place right now in the big leagues?

Building a brighter future takes more than amassing far-off talent: talent that may never arrive as advertised. It also means fostering development now, and the Pirates sacrificed excellent resources to do so when they shipped Hill and Santana out of town.