Ben Cherington’s position player draft record should be wake-up call for Pirates fans

When the Pittsburgh Pirates hired Ben Cherington as their general manager, his primary selling point was his extensive background in scouting and player development. The hope was that he could kickstart the organization's rebuild by stocking the prospect pipeline with young talent – which he has – but with arms, not bats.

Since he took over as general manager in November 2019, Cherington's first four draft classes have accounted for $61.3 million in signing bonuses for 64 of 69 picks. Of that total, $25.7 million has been spent on position players. Yet only two of those players – Henry Davis and Nick Gonzales – have reached the major leagues. That's unacceptable, especially for a team in a constant rebuilding state that's desperate for offense.

The imbalance reflects a philosophical miscalculation. Cherington’s front office prized velocity and pitch design while treating position players as secondary. The result? A system flooded with arms but starved of offensive impact. For every promising pitcher like Paul Skenes or Jared Jones, there’s a wave of stalled bats who never developed the approach or power necessary to survive in the modern game.

Ben Cherington's draft history doesn't bode well for Pirates' offense

The Pirates’ inability to draft and develop hitters has created a vicious cycle: a bottom-tier offense that forces the pitching staff to be nearly perfect, a lack of internal replacements when young bats stall, and a reliance on short-term veteran stopgaps. In other words, it's the exact opposite of what Cherington was hired to fix.

What makes this outcome especially damning is the context. Other small-market teams, like the Cleveland Guardians and Milwaukee Brewers, have turned modest draft pools into productive big-league lineups. The Pirates, meanwhile, have spent heavily on high picks without extracting value, suggesting the problem isn’t budgetary – but rather, evaluative.

As Cherington enters his sixth offseason, the results speak loudly: nearly $26 million spent on hitters, and only two have arrived. If this was supposed to be a developmental renaissance, it’s instead become a cautionary tale about the dangers of betting too heavily on theory and projection – and losing sight of players who can actually hit.