Paul Skenes is in line to win the NL Cy Young award this season.

It will mark just the latest achievement in the 23-year-old phenom’s short, but illustrious pro career. After winning NL Rookie of the Year last season, starting two straight All-Star Games, and leading baseball in WAR, ERA, strikeouts, and WHIP, winning a Cy Young is what we’ve come to expect from him.

His team, however, is a disaster.

In year two of Skenes, where the righty gave them a historic 1.97 ERA, 0.948 WHIP, 5.14 strikeout-to-walk ratio, and 216 total Ks over 187.2 innings, the Pirates once again found themselves massively underwater. Their early season start, which led to the firing of manager Derek Shelton after a 12-26 record to open the year, proved too much to even slightly come back from.

Despite some individual successes, it was another deeply disappointing season, one where their woes are now getting more and more national attention thanks to Skenes’ performance.

If the sport was simply called “pitching,” the Pirates would be among baseball’s top contenders. They have assembled one of the better rotations in the sport, and while Skenes obviously dominates the pitching talk in town and abroad, behind him sits an extraordinary cast of arms.

Mitch Keller, the elder statesman of the rotation, added another reliable season to his résumé. Though he had an unconventional start to close out his year, the righty posted a 4.19 ERA, 1.259 WHIP, and 2.94 strikeout-to-walk ratio in an impressive 176.1 innings. In his last four years, he’s been incredibly consistent, averaging a 4.15 ERA and never deviating more than 24 points from that figure.

Bubba Chandler, the top pitching prospect in baseball at the time of his long-awaited promotion, made waves late in the season when he took to the mound for the Pirates. In all, the righty he threw 31.1 innings to the tune of a 4.02 ERA, 0.926 WHIP. and 7.75 strikeout-to-walk ratio. One bad blowup against Milwaukee kept his stats from looking all the more impressive.

Johan Oviedo, who spent most of this season still recovering and rehabbing from Tommy John surgery before 2024, showed that he is still capable of holding down a rotation spot. In nine starts and 40.1 innings, the righty put up a 3.57 ERA, 1.215 WHIP, and 1.83 strikeout-to-walk ratio. Two years ago, he pitched to a 4.31 ERA, 1.373 WHIP, and 1.90 strikeout-to-walk ratio over 177.2 innings in his last full season in the bigs.

Mike Burrows steadied himself during his first real season in Pittsburgh. In 19 starts, 23 total games, and 96 innings, the righty amassed a 3.94 ERA, 1.240 WHIP, and 3.13 strikeout-to-walk ratio pitching out of the rotation and occasionally in long relief.

Braxton Ashcraft blossomed in the major leagues this season, after first appearing as a reliever and converting back to a starter later on. The right-hander totaled 69.2 innings and recorded a 2.71 ERA, 1.249 WHIP, and 2.96 strikeout-to-walk ratio. He looks more than ready of holding a full-time starting gig next year.

Jared Jones, who missed all of 2025 recovering from surgery, had a solid rookie season last year that saw him put up a 4.14 ERA, 1.192 WHIP, and 3.38 strikeout-to-walk ratio in 121.2 innings. The righty won’t be ready in time to start 2026, but he is gearing up for a mid-season return next summer.

That doesn’t even include other arms like lefty Hunter Barco, who will make an impact next season as well. They have the pitching side nearly entirely figured out. Assuming they can add an arm or two to their bullpen, it’s all shaping up really well.

Unfortunately, hitting the ball and getting on base are crucial components of the game of baseball, and it is two things that the Pirates have not been good at for several years.

Throw out the first three years of Cherington’s run. They were horrible, by explicit design. But even as this rebuild is supposed to be turning a corner, the offense still is not there.

In 2023, the Pirates were 23rd in batting average, 22nd in OPS, and had the tenth highest strikeout figure.

In 2024, the Pirates were 24th in batting average, 27th in OPS, and had the fourth highest strikeouts.

This year, they were 28th in batting average, dead last in OPS, and were seventh highest in strikeouts.

Somehow, they are only getting worse.

Those poor batting stats mirror their diminishing rankings in the standings. In 2023, they finished 23rd in league-wide standings. In 2024, they finished 24th. This year, they finished 26th.

Cherington’s teams have consistently lacked offense, and it is detrimental to the club. The Pirates have a playoff-caliber rotation, and yet the supporting offensive cast has kept this team out of even the playoff conversation, let alone actually participating in October baseball.

Yet on Monday, shortly after a Pittsburgh Post-Gazette piece by Noah Hiles in which players anonymously blasted the Pirates organization for all their flaws, Cherington said he received assurance that he will be back as the GM next year.

Fans, understandably, erupted online as the news trickled out into the masses, mixed with the announcement of manager Don Kelly’s extension. It was a completely tone deaf move that did nothing to help this team’s reputation in town, which just seems to get worse every day.

Bringing back the guy who has never gotten his team past the 76-win mark feels as close to a death sentence as possible for the 2026 season, which is massively important to the club.

Next year brings with it a lot of milestones. It will mark year three for Skenes, in a year where he, in all likelihood, will just be dominate as the first two. It will also mark possibly the final year for franchise legend Andrew McCutchen, assuming he is willing to re-sign for another year.

Skenes deserves playoff baseball. McCutchen deserves playoff baseball. But most importantly, Pirate fans deserve playoff baseball.

It also could end up being the last ride for a little while. Talks of implementing a salary cap are more serious than ever, and if the Players Association stands their ground in opposition, things could get ugly and labor could stop.

The threat of a 2027 lockout would put all the more pressure on the Pirates to win next year, and would make a failed 2026 season all the more disappointing.

Even if that doesn’t happen, though, the Skenes window is already closing. At the very, very least, the window for building a team around him while his contract is cheap is rapidly closing. You have to take advantage of it.

That means getting aggressive this offseason. It means bringing in actual, established big league hitters to help supplement one of the sport’s worst offenses. They’ll need at least one outfielder and one left-side infielder. It’s the perfect opportunity to bring in bats.

With owner Bob Nutting, inexcusably once again, not expected to make any major increase to the payroll, the trade market is this team’s best, and probably only, route to success.

Spencer Horwitz was a good offseason trade last year. The first baseman missed the first month and a half after recovering from offseason wrist surgery, and he did start out rather slow as he was forced to acclimate on the fly.

After the All Star break, though, Horwitz slashed .305/.396/.520 (.916 OPS) with nine home runs and 35 RBI in 62 games. Overall, he finished the season as the team’s leader in OPS, at .787. He filled a serious need at first base and brought a good bat with him.

But if there’s ever been a poster child for a “too little, too late” move by a general manager, it’s Horwitz.

There’s just not a résumé in Pittsburgh that says Cherington is capable of assembling enough of an offense. His other big move in the offseason, free agent signing Tommy Pham, is an example of that. The outfielder had a rollercoaster run, from an ice cold spring to a blistering hot summer, but it ended with a .245/.330/.370 (.700) slash line. It’s not good enough.

The bottom line is this: for however good of a job Cherington has done with the pitching staff, and for whatever smaller moves at other positions that could work out, there’s one number that ultimately matters.

71-91.

Six years into a rebuild, a record like that is unacceptable. There’s nothing else to call it.

We can argue whether, in baseball’s current economic landscape, a small market team like the Pirates could ever win the World Series. Only twice in the last 15 years has a World Series winner not ranked in the top ten in payroll. Houston’s 17th-place payroll back in 2017 was the lowest for a champion in that span.

But I know for a fact that small market teams can perform much better than this. Much, much better.

The magic number for a wild card spot this season was 83. Cincinnati made it with a record of 83-79.

Six years in, and Cherington’s Pirates couldn’t even come close to that. In fact, they’re only going in the wrong direction. Bringing him back is a major mistake, one that could sadly define the rest of the Skenes era in Pittsburgh.