The Pittsburgh Pirates will return to the field for their first post-All-Star break game against the Chicago White Sox at PNC Park on Friday night.

It’s another lost season on the North Shore. The Pirates remain buried in the National League Central, where they have resided for most of the season. Their 39-58 record is fourth-worst in baseball. They need to go 43-22 over their final 65 games to even break .500.

There won’t be a World Series in Pittsburgh. There won’t even be a playoff game. But there are these five storylines to follow.

Can Paul Skenes Win Cy Young?

Paul Skenes started his second-straight All-Star Game for the National League, a reflection of his emergence as arguably the top starting pitcher in baseball.

It was another flawless performance in the Midsummer Classic for the Pirates’ ace, and it’s been an equally as flawless season with Pittsburgh.

Skenes’ leads all MLB starters with a sparkling 2.01 ERA. He’s struck out 131 batters in 121 innings. Opponents are hitting .189 against him with a .532 OPS. It doesn’t get much better than that.

The only blemish is Skenes’ 4-8 record. It’s a reflection of  how the Pirates have played this season, not how he has pitched. It also shouldn’t factor into the minds of voters of the award, but it might.

If Skenes did win the National League Cy Young, he would be the third Pirate to win the award, joining Vern Law in 1960 and Doug Drabek in 1990.

Will Cherington and Kelly Return to Pirates in 2026?

Ben Cherington has worn out his welcome among many fans, but he remains the Pirates’ general manager.

Cherington has yet to build a winner in Pittsburgh. He has yet to come close, for that matter. But as out John Perrotto reported several days ago, there’s a legitimate chance he returns to the Pirates in 2026.

If Cherington returns, one has to think Don Kelly will be back as manager next season. The Pirates, though still far from perfect, have played better under Kelly, and he’s someone the clubhouse has a lot of respect for.

But if the Pirates collapse even further in the second half and Cherington doesn’t return, the new GM will get to pick the manager.

Who Stays? Who Goes?

Newsflash: The Pirates will be sellers this trade deadline. OK, that’s hardly newsworthy, but the team could look a lot different come Aug. 1.

The rentals will all likely be playing elsewhere after the deadline. The Pirates already traded Adam Frazier to the Kansas City Royals. Andrew Heaney, Isiah Kiner-Falefa, Tommy Pham and Caleb Ferguson are all likely to go too.

But after that, the Pirates have some tough decisions to make. Do they trade David Bednar and/or Dennis Santana, even though both are controlled through next season? Do they trade Mitch Keller for lineup help? Do they consider getting Ke’Bryan Hayes’ contract off the books?

Everything is on the table, and the Pirates will do whatever it takes to have a better offense in 2026 and beyond.

Bubba Chandler’s Debut

Fans have been patiently awaiting the debut of top pitching prospect Bubba Chandler all season, but the Pirates have their reasons for not calling him up yet.

One of those reasons is that Chandler has dealt with some command issues, but he’s been much better in his past few starts. Through 18 starts with Triple-A Indianapolis this season, he’s 4-2 with a 2.82 ERA.

Chandler is getting close. And once the Pirates inevitably trade at least one of their starting pitchers, he could be a replacement.

Can Cruz Go 30/30… or 40… or 50?

One of my preseason predictions was that Cruz would have a 30/30 season. He’s well on his way to 30 stolen bases, in fact, he leads the National League with 29.

But Cruz will need to pick it up with the power if he wants to reach 30 home runs. Currently, the 2025 Home Run Derby participant is at 16 home runs, so he’ll need to hit 14 more over the final 65 games of the season.

Can he get there? How many stolen bases will he end with? And will he end up leading the league in steals?