Series Preview: Pittsburgh Pirates at Boston Red Sox

Ask not for whom the bell Tolles.

Summarized by AI ⓘ

What is the story about?

The Red Sox swept the Baltimore Orioles in four games to make up for losing two at Fenway Park and their return home is…Paul Skenes? Well, there’s also Payton Tolle.

The Pittsburgh Pirates aren’t great. And that’s being rather generous, although the Colorado Rockies exist too. The Pirates are a last place team in the NL Central but at 59-76 arn’t too far removed from the Los Angeles Angels (62-71) as opposed to the 38-win Rockies or 48 win White Sox.

The Nationals with the starting of a young core around James Wood have won 53 games. One of the reasons why: Paul Skenes.

The 2024 sensation is living up to the hype in his sophomore season. Fresh off a Rookie of the Year he leads the NL in ERA and FIP through 27 starts and is a very likely Cy Young winner. The best thing for the Red Sox about facing him is that his record is 8-9. The Pirates have won 14 of his starts and lost 13. If you can get this into the bullpen…well, anything can happen and the Sox are able to walk it off this series.

Skenes will be facing Payton Tolle making his major league debut. The southpaw turns 23 in November, is a product of the 2024 draft (2nd round) and simply blazed his trail through the minor leagues. His pedigree isn’t Skenes’, obviously, but if he sticks the landing in his debut this could be an excellent matchup.

Dustin May was bumped from Friday to face Johan Oviedo. In what seems to be a theme for Boston recently, Oviedo is returning from Tommy John surgery that cost him the 2024 and most of the 2025 season. In 10 innings spread across three starts – 1.0, 5.0, 4.0 innings – he’s allowed 4 runs on 7 hits with 14 strikeouts. Dustin May, already two Tommy Johns in, knows things can go south quickly.

Mitch Keller is the Pirates’ Old Reliable. He’s in his seventh season as a Pirate. He gets a few Ks but they’ve been in decline the last few years: just 125 in 150 innings in 2025. He doesn’t walk many, which helps. He was rumored to be available at the deadline and perhaps the Sox were interested but in the end Ben Cherington held on. He was signed to an extension through 2028 so he could fetch something this winter, although the Sox are likely looking to add more of a front-line starter.

Lucas Giolito is coming of a stellar start against the Baltimore Orioles.

Roman Anthony is on a power binge.

There isn’t much to say about the Pirates. They just aren’t very good. Oneil Cruz lost almost 100 point of OPS since 2024 slashing just .203/.302/.391. Andrew McCutchen is looking like he’s about at the end of his rope. It’s a sad state of affairs. The Pirates aren’t abysmal but they probably are terrible. They’re not hopelessly outside of contention for a Wild Card but aren’t close either. Is Paul Skenes their Mike Trout? For his sake, hopefully not in the same way…suffering through mediocre season after mediocre season.