82 Wins Raised the Standard: The Pirates’ Path to October in 2027

The Pittsburgh Pirates’ 82–80 finish deserves recognition. An 11-win improvement and a substantial offensive turnaround represent meaningful progress.

They also raise expectations. Pay attention to this post Ben, Trey, and Bob! The front office, led by Ben Cherington, have work to do this off season! The big focus should be on building a team that can withstand injuries, inconsistent performances, and a competitive National League playoff race - with a focus on catching the Brewers, but also understanding that the wild card is in the post-season... and you just need to get in with the right weapons to win consecutive short series. And the Pirates are not as far from that last part as people might think!

1. Where the Pirates Were... and Where They Are Now

What the data tells us: Pittsburgh increased its scoring by approximately 32%, but runs allowed increased by nearly 15%. The offense made a substantial leap; weaker run prevention absorbed part of that improvement.

A positive run differential supports the conclusion that this was a better team. There simply is no question. It also tells us that the Bucs do not have enough depth to sustain playoff contention.

Cherington’s assignment: Preserve the offensive gains while improving pitching and defense. Treating 82 wins as evidence that the roster only needs minor adjustments would underestimate the remaining work.

2. Paul Skenes: Make Readiness the Priority

Skenes remains central to Pittsburgh’s chances in 2027. His comments about the WBC may hold some water, but the responsibility is in his corner. His offseason preparation deserves particular attention after a season marked by diminished velocity and adjustments to his delivery.

The performance evidence: Reporting documented declining fastball velocity and multiple mechanical changes. Those developments warrant investigation, but they do not establish an undisclosed injury.

What the data tells us: Evaluating his readiness requires more than an ERA or a single radar-gun reading. The Pirates should track:

• Fastball velocity and movement across outings.

• Command and consistency of release.

• Swing-and-miss rates across his arsenal.

• How effectively he maintains his stuff deeper into games.

• Recovery between starts.

Cherington’s assignment: Ensure Skenes, the coaching staff, and the medical and performance teams share a coordinated offseason plan. The goal should be repeatable, effective pitching over a full season.

The roster must also provide enough support that Skenes does not need to compensate for every other weakness.

3. The Rotation Is VERY Good Now, but could use insurance.

What the data tells us: Ashcraft and Jones provide reasons for optimism. Chandler’s approximately 4.7 walks per nine innings identify command as a major development priority. We have seen Bubba be top shelf, and seen him not be able to hit the broad side of a barn. We need him to be closer to top shelf. Keller’s results make it difficult to count on an automatic return to form, in spite of how good he was in April and May.

A promising rotation can still be vulnerable when its success depends on several improvements occurring simultaneously.

Cherington’s assignment: Acquire a dependable major-league starter and maintain additional starting depth. A credible sixth option would help Pittsburgh manage workloads and injuries while keeping useful relievers in their best roles.

Internal improvement should strengthen the rotation beyond its baseline. It should not be required merely to make the rotation functional.

4. Build the Bullpen Around Weaver

What the data tells us: The bullpen improved substantially. Its second-half performance should inform the offseason plan, while recognizing that relief results can fluctuate. This is important because how BAD it was pre-trade deadline. The Pirates need to build around the end of season pen, not do what they did last offseason.

Luke Weaver is already under contract through 2027. That gives Pittsburgh an established late-game option to build around. If Weaver is Weaver in April, the Pirates need to look at extending him before he walks, but I would not do that over the offseason with so many other holes to fill. If Weaver walks after the Bucs make the playoffs in 2027, that won't be great - but it also means the team did what they needed to get in the dance, and that will be enough for 2027 to go out and find another 9th inning assassin.

Cherington’s assignment: Keep Weaver as the primary closer and add another proven high-leverage reliever. Build enough depth to protect leads when the preferred setup pitchers are unavailable.

Weaver’s role can accommodate occasional earlier use against an opponent’s most dangerous hitters. The broader objective remains clear: get leads to him without exhausting the same small group of arms.

5. Re-Sign Brandon Lowe—and Preserve the Offensive Gains

What the data tells us: Lowe supplied substantial production. His departure would create a major replacement task before Cherington could address the team’s other needs.

Re-signing him would preserve an important part of the current offense. Additional improvements would still be necessary.

Cherington’s assignment: Make a competitive offer early. Contract length, age and future defensive value deserve consideration, but those concerns should lead to a serious negotiation. Let's be clear.... simply resigning Lowe isn't enough, but it is essential.

Ownership must provide the resources to retain production and improve the roster. If Lowe leaves, Pittsburgh needs an established replacement rather than an assumption that its young hitters will collectively cover the loss.

6. Improve Lineup Balance and Defense Together

The Pirates scored 4.73 runs per game, but allowed 4.56. That narrow margin illustrates why preventing runs matters alongside adding another bat.

What the data tells us: Pittsburgh can improve without another dramatic increase in total scoring. Better defense, fewer avoidable baserunners and stronger performance across lineup matchups can make the existing offense more valuable.

Cherington’s assignment: Target a hitter with a sustained record against left-handed pitching who also contributes defensively. Evaluate several seasons of platoon performance rather than buying one unusually strong split.

Position should depend on the final roster. The acquisition should reduce the number of games in which the manager must choose between acceptable offense and acceptable defense.

7. Catcher: Give Flores the Opportunity, Davis the Supporting Role

Rafael Flores Jr.: An Encouraging Offensive Start

What the data tells us: Flores demonstrated enough offensive potential to earn an extended opportunity. The sample remains too small to establish his long-term production.

His next challenge is maintaining a productive approach as opponents adjust while continuing to develop behind the plate.

Recommended role: Enter spring training with Flores as the leading candidate for primary catching duties. Evaluate his receiving, blocking, throwing and preparation alongside his offense.

Henry Davis: Value as a Defensive Backup

Davis’s defensive development offers a useful complement to Flores, even while his offensive production remains limited.

What the evidence tells us: A catcher can help a winning roster without becoming a middle-of-the-order hitter. Defense and dependable work with the pitching staff have value in a supporting role.

Recommended role: Use Davis as the defensive backup, with meaningful starts and opportunities to contribute. Any offensive improvement would strengthen the position; the roster should not depend on it.

Endy Rodríguez: Keep Him in the Mix, Respect the Recovery

What the data tells us: Rodríguez showed offensive promise. His recovery creates uncertainty about when he can resume the demands of major-league catching. Returning to baseball activities and being ready to catch regularly are separate milestones.

Recommended role: Keep Rodríguez in the long-term competition while building an Opening Day plan that works without him. Flores and Davis should have additional depth behind them, allowing Rodríguez to return based on readiness. And there may come a point where Endy pushes Davis out... or, more likely, is a trade deadline trade chip! Yes, I like Flores more than Rodriguez for the future of this team.

8. What a Successful Offseason Looks Like

Cherington’s priorities should be concrete:

1. Re-sign Lowe or replace his production with an established hitter.

2. Prepare Skenes for a healthy, effective full season.

3. Add a dependable starter and protect rotation depth.

4. Strengthen the bullpen around Weaver.

5. Improve defense and lineup balance.

6. Develop Flores, use Davis’s defensive strengths and give Rodríguez adequate recovery time.

The Pirates do not need every young player to become a star to contend. They need a roster that can absorb ordinary setbacks without losing months of competitive baseball.

Eighty-two wins gave Pittsburgh something worth building upon. The next offseason should produce a team with enough depth and proven production to make October a realistic expectation.