Ben Cherington’s roster problem is sitting on playoff benches in October.
That’s the sharpest way to read the Pittsburgh Pirates’ latest reminder of how far they still have to go. Four players who were once asked to do far more in Pittsburgh than they were built for are now on Wild Card Series rosters with other clubs: Rowdy Tellez, Tommy Pham, Bryan De La Cruz and Isiah Kiner-Falefa.
In other words, players playoff teams view as useful extras were treated by the Pirates as everyday answers.
Tellez is with the Atlanta Braves as a bench bat. Pham is a reserve outfielder for the Chicago White Sox.
De La Cruz gives the Philadelphia Phillies outfield depth. Kiner-Falefa is a utility piece for the Boston Red Sox.
Those are all sensible roles for those players. In Pittsburgh, they were pushed into much bigger jobs.
Tellez played in 131 games for the Pirates in 2024 and came to the plate 421 times, hitting .243/.299/.392 with 13 home runs. He was brought in to supply power at first base, but the production never matched the role.
De La Cruz arrived from the Miami Marlins at the 2024 trade deadline as a boost for a struggling lineup. He hit .200/.220/.294 with three home runs in 44 games, then got regular outfield chances before the Pirates non-tendered him that offseason.
Pham’s turn came in 2025. He appeared in 120 games, logged 449 plate appearances and hit .245/.330/.370 with 10 home runs.
Kiner-Falefa was just as heavily used. He appeared in 119 games in 2025 and posted a .632 OPS over 428 plate appearances.
None of that means those players couldn’t help a good team in the right spots. It does mean they were asked to carry too much in Pittsburgh. That’s the difference October makes clear.
The Braves, White Sox, Phillies and Red Sox are comfortable using them as matchup pieces, pinch-hit options, late-game substitutes or spot starters. The Pirates kept treating them like foundational bats.
That’s the real indictment of Ben Cherington’s roster-building.
This isn’t about arguing Pittsburgh should have held onto all four. It’s about the organization leaning too often on other teams’ depth as if it were starting-caliber talent. For a club that does have a promising young core, that’s a costly way to operate.
The Pirates did finally get to 82-80 in 2026, their first winning record in a long stretch and a snap to the streak of losing seasons. But they still missed the playoffs, and the postseason drought keeps growing into something uglier than any single bad year.
There’s nothing wrong with signing Pham for depth. There’s nothing wrong with adding Kiner-Falefa for versatility. There’s nothing wrong with having Tellez around as a left-handed power option.
The problem is what happens when those kinds of players are forced into jobs they’re not suited to because the team hasn’t built anything better around them. That’s the line playoff organizations understand and the Pirates have kept crossing.
Cherington has had seven seasons to shape this roster. Pittsburgh still looks like a team that has not fully learned the difference between complementary players and everyday answers.
And right now, four former Pirates regulars are getting ready for October baseball while the Pirates are home again, stuck with the cost of pretending those players were the solution.
In Other News...
Former Pirate Joe Musgrove Just Got A Painful October Reminder
Joe Musgroves return to a major league mound finally arrived Tuesday night in San Diego, and it came with the kind of October stage that can make every pitch feel heavier. In the Padres 8-0 win over the Cubs in the National League Wild Card Series, the former Pirate got into the game in the ninth inning and finished off a scoreless frame, striking out the final batter while working around two hits and a walk.
For Pittsburgh fans who watched Musgrove develop into a dependable arm before moving on, the appearance was a reminder of how long his road back had been. Nearly two years had passed since his last major league pitching appearance, and the comeback has taken him through Tommy John surgery and more than one setback before he could get back in front of a postseason crowd. [Read more 🡒]
Pirates Fans Just Got An October Reminder That Stings
Postseason baseball can expose the gap between a good regular season and a true October stage, and Houstons opening game in the American League Wild Card Series offered a reminder of how quickly the mood can turn. The Astros drew a crowd of 34,011 at Daikin Park for their matchup with the White Sox, but some fans still let the home team hear it, a jarring scene for a club that has spent years expecting deep October runs.
For Pittsburgh, it is the kind of scoreboard comparison that stings a little more than usual. The Pirates finished the regular season with a better record than Houston, yet they are watching the playoffs from home because of the realities of divisional standings, while the Astros are still playing in October despite their own uneven moment with the crowd. It is a clean example of how one team can end up in the tournament and another can miss out, even when the records do not fully tell the same story. [Read more 🡒]
Nick Gonzales Just Became A Real Pirates Offseason Dilemma
Nick Gonzales gave the Pirates plenty to like at the plate in 2026, but his work at third base left the club with a tougher question than it would prefer heading into the offseason. He logged the worst defensive metrics among third basemen with significant playing time, turning what looked like a useful infield solution into one of Pittsburghs more complicated roster discussions.
Ben Cherington and Don Kelly have not settled on where Gonzales fits defensively going forward, and that conversation is still playing out in offseason exit meetings. The Pirates know the offense was real, but the challenge now is figuring out whether the bat is best served by keeping him at third or moving him somewhere that better protects both him and the club. [Read more 🡒]