Ben Cherington's biggest Pirates roster failures are hiding in plain sight on playoff benches

If you want a perfect illustration of everything wrong with the Pittsburgh Pirates' roster construction under general manager Ben Cherington, look no further than the benches of this year's MLB playoff teams.

Rowdy Tellez. Tommy Pham. Bryan De La Cruz. Isiah Kiner-Falefa.

All four are on Wild Card Series rosters this October. And all four were regular fixtures in the Pirates' starting lineup at some point over the past two years.

Tellez is a bench bat for the Atlanta Braves. Pham is a reserve outfielder for the Chicago White Sox. De La Cruz is providing outfield depth for the Philadelphia Phillies. Kiner-Falefa is a utility option for the Boston Red Sox.

These are players whom legitimate playoff contenders consider complementary pieces. In Pittsburgh, they were routinely expected to be everyday contributors.

And somehow, Cherington still hasn't figured out why his team keeps missing the postseason.

Former Pirates starters finding playoff opportunities as bench players exposes Ben Cherington's roster-building problem

Consider just how heavily Pittsburgh relied on these four players.

Tellez appeared in 131 games for the Pirates in 2024, receiving 421 plate appearances while hitting .243/.299/.392 with 13 home runs. He was supposed to provide much-needed power at first base, but instead became another example of the Pirates settling for an underwhelming offensive option.

De La Cruz was acquired from the Miami Marlins at the 2024 trade deadline to bolster Pittsburgh's struggling lineup. He proceeded to hit .200/.220/.294 with three home runs in 44 games. The Pirates gave him regular opportunities in the outfield before non-tendering him that offseason.

Then came 2025. Pham appeared in 120 games, receiving 449 plate appearances while hitting .245/.330/.370 with 10 home runs. Kiner-Falefa, meanwhile, appeared in 119 games and posted a .632 OPS across 428 plate appearances.

Neither player was necessarily incapable of contributing to a winning baseball team. But neither should have been counted upon to carry the workload Pittsburgh assigned him. That's what makes their current postseason roles so revealing.

Other organizations are perfectly comfortable having these players available for occasional starts, favorable matchups, pinch-hitting opportunities or late-game substitutions. They're not asking them to be foundational pieces of their offense.

The Pirates did. And that's the indictment of Cherington's approach to roster construction.

To be clear, this isn't an argument that Pittsburgh should have retained these four players. Quite the opposite, actually. It's an argument that the Pirates have spent far too many seasons treating other teams' bench depth as their own starting-caliber talent. For a club with an increasingly promising young core, that's a particularly frustrating way to waste opportunities.

Pittsburgh finally finished with a winning record in 2026, going 82-80 and snapping its streak of losing seasons. Yet the Pirates still missed the playoffs, extending a postseason drought that has become far more embarrassing than any individual losing season.

There's nothing wrong with signing a veteran like Pham to provide depth. There's nothing wrong with acquiring someone like Kiner-Falefa for his defensive versatility. There's nothing wrong with having a left-handed power option like Tellez available off the bench.

The problem arises when those players are asked to fill roles they're not adequately equipped to handle because the organization hasn't invested enough in better alternatives. That's the distinction playoff teams appear to understand and the Pirates have repeatedly failed to make.

Cherington has spent seven seasons assembling this roster. Pittsburgh shouldn't still be learning that complementary players aren't substitutes for legitimate everyday talent.

Four former Pittsburgh regulars are getting ready for meaningful October baseball, and the Pirates are watching from home again. Not because they let those players leave, but because they spent so much time pretending those players were the answers in the first place.

Add us as a preferred source on Google

Follow