Cubs vs. Pirates — Keys to the Series, Projected Starters, and the Justin Steele Reality Check
The Cubs do not get a soft landing here. Pittsburgh has the next four lined up, Paul Skenes is waiting at the back end, and Chicago’s side of the rotation is still fluid behind Ben Brown. If the Cubs are going to stop the slide, they need to win the first three days — because Thursday looks like a problem.
First things first: this is a four-game set in Pittsburgh, not a three-gamer. MLB’s probable pitchers page has Ben Brown vs. Carmen Mlodzinski locked in for Monday, while the Pirates already have Braxton Ashcraft, Bubba Chandler, and Paul Skenes lined up behind him. The Cubs, meanwhile, still show TBD for the final three games. That matters because Chicago’s margin for error changes dramatically by the end of the series.
| Game | Cubs | Pirates | Read |
|---|---|---|---|
| Game 1 | Ben Brown (confirmed) | Carmen Mlodzinski (confirmed) | Best shot to strike early |
| Game 2 | TBD — Jordan Wicks leading candidate | Braxton Ashcraft | Likely bridge game |
| Game 3 | TBD — Jameson Taillon earliest fit | Bubba Chandler | Must avoid falling behind in series |
| Game 4 | TBD — Colin Rea earliest fit | Paul Skenes | Hardest matchup on paper |
// THE JUSTIN STEELE REALITY CHECK
Justin Steele is not the probable for this series. In fact, his late-April flexor-strain setback pushed his target return into the second half/after the All-Star break, and multiple recent Cubs injury updates still frame him as sidelined rather than imminent. If you were hoping this series was the Steele return spot, it isn’t.
1. Ben Brown Has to Hold the Opener
Brown does not need to dominate. Brown needs to keep the game under control long enough for the offense to breathe. That is the assignment. He enters the opener with a 2.09 ERA on MLB’s probable page, and that makes this the best-looking Cubs starter slot actually confirmed for the series. If the Cubs waste this game, they are voluntarily handing leverage away before the hard part of the set even arrives.
Mlodzinski is beatable. The Cubs do not need a masterpiece against him — they need a lead, traffic, and competent sequencing. This is the night to get the bullpen back on your side instead of asking it to absorb another game from behind.
2. Stop Talking About Justin Steele Like He’s Walking Through That Door
There is a difference between “coming back this season” and “relevant to this week.” Steele is the first one, not the second one. His setback turned what had once looked like a Memorial Day-ish target into a second-half timeline. So the article cannot honestly be “Steele returns and changes everything.” What changes everything in this series is not Steele — it is whether Chicago can survive the TBD portion of its own rotation.
If you were writing this series around Justin Steele, you were writing the wrong series. This one belongs to the depth arms, whether the Cubs like it or not.
3. Tuesday Is the Pivot Point
Because Edward Cabrera hit the injured list with a blister and Jordan Wicks was summoned back to the majors, Tuesday looks like the swing game. Wicks is the leading candidate for that spot, even though MLB’s probable page still lists the Cubs as TBD. That makes Game 2 more than just another night in the set: it is the moment where the Cubs either prove they can patch the rotation or reveal that this week is about survival rather than advantage.
// WHY TUESDAY MATTERS
- Ashcraft is not a pushover — 2.89 ERA through ten starts.
- Chicago’s side is unsettled — Wicks is plausible, but not yet official.
- The series can tilt here — win Tuesday and you can still stay out in front of Thursday’s problem.
4. Attack Before Skenes, Not During Skenes
This should be obvious, but the Cubs have not exactly been playing obvious baseball lately. Pittsburgh already has Skenes circled for Thursday, and another Cubs/Pirates preview put it bluntly: if Chicago’s offense is going to wake up, it probably needs to happen against Mlodzinski, Ashcraft, or Chandler, not at the end of the series.
That means the Cubs cannot treat the first three games like setup acts. They need urgency immediately. Score first. Make the Pirates use leverage innings early. Avoid the lazy comfort of saying “we’ll get them tomorrow.” Tomorrow in this series eventually becomes Paul Skenes.
5. The Cubs Have to Win the Contact Battle
The Pirates’ run-prevention path in this series is simple: keep the game close, wait for Chicago to chase, and let the Cubs beat themselves with dead innings. The Cubs’ answer has to be just as simple.
- Fewer empty strikeouts
- More count leverage
- Better at-bats with runners on
- Pressure before two strikes
That is where Pedro Ramírez matters, too. His RBI double in his debut was not just a nice moment — it was evidence that the lineup can still get instant, non-theoretical impact from a fresh bat. If that carries over at all, it gives the Cubs a chance to change the rhythm of the bottom third.
6. Projected Cubs Path Through the Four Games
Final Take
The cleanest version of this series is simple: take one of the first two, win one of Brown/Wicks, and do not let the set reach Thursday with everything hanging by a thread. That is the map. The Pirates have made theirs obvious. The Cubs’ side is more chaotic, but the strategy is still there if they are disciplined enough to execute it.
And that is the real key to beating Pittsburgh: stop waiting for the perfect version of the Cubs to show up. Justin Steele is not walking in to save this series. The Cubs have to win it with the arms available, the bats already here, and the urgency that should come from knowing Skenes is sitting at the end of the runway.