Pirates Short Road Trip vs. Cubs: Five Things to Watch
In this story:
CHICAGO — After their five-game winning streak was snapped and a spirited home stand ended with a slight thud against the San Diego Padres, the Pittsburgh Pirates try to regroup on the road Friday afternoon at Wrigley Field, opening a three-game series against the Chicago Cubs.
Earlier this week, the Pirates (7-5) dropped their first series since the opening week, falling twice to the star-powered Padres. The bats went quiet at the worst moments, and the bullpen showed rare cracks. Now, Pittsburgh packs its bags for a short but pivotal three-game trip to the North Side before returning home next week. It’s an early test of resilience for a young team that has grown some confidence, and a chance to prove that last week’s hot streak was no fluke.
Chicago (6-6) enters Monday night’s opener under a very different kind of pressure. Just two days ago, the organization announced that Cade Horton, the 2022 first-round pick and one of baseball’s top rookies last season, would undergo season-ending elbow surgery. The loss is a gut punch to a rotation already searching for consistency, and it leaves the Cubs leaning even harder on veterans and unproven arms to navigate a crowded NL Central. Wrigley Field, always a cauldron of wind and noise, will offer no comfort.
With both teams sitting near .500 and looking to gain early separation in the division, here are five things to watch as the Pirates head to Chicago for this three-game set.
Here are five Pirates-centric things to watch in the upcoming series against the Cubs at Wrigley Field, based on the 2026 season's developments so far.
1. Can the Rotation Hold Up Without Skenes?
The Cubs caught a scheduling break: Paul Skenes, the reigning NL Cy Young winner, is not expected to pitch in this three-game set after starting against the Padres on April 7. That puts the spotlight squarely on the rest of the rotation. So far this season, they've answered the call.
Carmen Mlodzinski gets the ball in the opener, and while he has kept his ERA below 4.00 in each of his first three MLB seasons, transitioning between bulk relief and starting has been a fluid process for him. He has looked particularly comfortable as a starter this season, but his troubles facing the order the third time could still rear its ugly head.
Behind him, Braxton Ashcraft and Bubba Chandler will need to prove they can deliver consistency, something that has been a hallmark of Ashcraft's career but that has eluded Chandler early on. The flamethrowing rookie has walked 10 batters over his first two starts and openly expressed frustration about "setting the team up for failure". With Skenes unavailable, this series is another test of the Pirates' pitching depth.
2. The Ozuna Gamble Is Already Under Scrutiny
One of the Pirates' off-season additions to boost a historically bad 2025 offense has gotten off to a nightmare start. Marcell Ozuna, signed to a one-year, $12 million deal, has just two hits in his first 31 at-bats—a .065 average—leading manager Don Kelly to bench him earlier this week in favor of Brandon Lowe at designated hitter against the Padres.
Lowe, acquired from Tampa Bay, has been everything Pittsburgh hoped: three home runs, a .821 OPS, and a pair of homers on Opening Day. The DH spot is at risk of becoming a revolving door, and with Wrigley's swirling winds testing any hitter, how Kelly deploys Ozuna (or doesn't) will be a storyline all series.
Ozuna's off the field issues have drawn scrutiny from baseball fans, and his on-field performance isn't doing anything to gain him support.
3. Konnor Griffin's First Road Series
The 19-year-old phenom's career continues to play out like a storybook, with his first MLB road series at historic Wrigley Field. Konnor Griffin, whom the Pirates locked up to a massive $140 million extension earlier this week, has already made his mark on the big-league roster, providing stable defense and a consistent threat on the basepaths. The bat will come in time.
Griffin's athleticism and potential is undeniable, but the rookie will face a tough test at Wrigley.
4. Will the back end of the bullpen continue its strong run?
Kelly still hasn't committed to a definitive closer, choosing to split the role between Dennis Santana and Gregory Soto. So far, that formula has worked beautifully.
Santana has built on his strong 2025 season, not allowing a run and striking out four batters over six innings thus far. Soto, the hard-throwing lefty acquired to handle high-leverage situations, has been nearly untouchable, allowing just one earned run across seven appearances with 13 strikeouts. He is fifth in strikeouts in MLB amongst relievers.
But Wrigley Field is a different beast. The wind can turn routine fly balls into nightmares, and the Cubs' lineup, featuring the speed of Pete Crow-Armstrong and the veteran savvy of bats like Alex Bregman, won't go quietly. If the starters can't go deep into the game, Santana and Soto may be asked to record four or even five-out saves. How they handle that extended workload in a hostile environment could be the difference between a winning road trip and a losing one.
5. Bounce back after the Padres series
The Pirates entered the Padres series riding a five-game winning streak and looking like a playoff contender. They left having dropped two of three, with the offense going quiet in critical moments.
The good news? Pittsburgh is still 7-5 and has a +6 run differential, a sign that the early success wasn't a fluke. But the Cubs are a divisional opponent, and Wrigley Field is never an easy place to right the ship. How this young team responds to its first real adversity of 2026 will tell us a lot. Can they shake off the San Diego hangover and get back to the brand of baseball that won five straight? It's a long summer, but it may tell us a lot about whether this season is different from the Pirates' recent struggles.
Key Stats
- Pokin' Pirates: .272 BA over last seven days is fourth in MLB
- Crushin' Cubbies: 7 HR over last seven days is fourth in MLB
- The Pirates and Cubs have met a total of 2,621 times. The Pirates lead the series 1,317-1,287-17.
Probable Pitchers & Matchups
Game 1: Friday, 2:20 PM EDT at Wrigley Field
- PIT: RHP Carmen Mlodzinski (0-0, 4.00 ERA, 13 K in 2026)
- CHC: LHP Shota Imanaga (0-1, 4.50 ERA, 11 K in 2026)
- Key Battle: Mlodziinski vs Cubs SS Dansby Swanson (4-for-7, 1.196 OPS in seven career AB against Mlodzinski)
Game 2: Saturday, 2:20 PM EDT at Wrigley Field
- PIT: RHP Braxton Ashcraft (1-1, 2.25 ERA, 11 K in 2026)
- CHC: RHP Edward Cabrera (1-0, 0.00 ERA, 9 K in 2026)
- Key Battle: Ashcraft vs Cubs 1B Michael Busch (1 HR in five career AB against Ashcraft)
Game 3: Sunday, 2:20 PM EDT at Wrigley Field
- PIT: RHP Bubba Chandler (0-1, 3.12 ERA, 10 K in 2026)
- CHC: RHP Jameson Taillon (0-1, 2.53 ERA, 7 K in 2026)
- Key Battle: Taillon vs Pirates OF Bryan Reynolds (.263 AVG, .807 OPS, 1 HR, 1 RBI in 19 career AB against Taillon)
Players to Watch
- SP Braxton Ashcraft (PIT): 6 IP, 1 ER, career-high 8 K in last start
- 1B/OF Ryan O'Hearn (PIT): .316/.409/.579, 1 HR, 4 RBI over last seven days
- SP Edward Cabrera (CHC): Has not allowed a run in first two starts of season
- 3B Matt Shaw (CHC): .294/.368/.706, 2 HR, 3 RBI over last seven days
Ethan Merrill is from Grand Rapids, MI, and brings with him a diverse background of experiences. After graduating from Michigan State University with a degree in journalism, he worked with the Arizona Diamondbacks for three seasons before settling in the Pittsburgh area in 2020. With a passion for sports and a growing connection to his community, Ethan brings a fresh perspective to covering the Pittsburgh Pirates.