Cubs vs. Pirates Prediction: Can Chicago Solve a Slumping Paul Skenes?

Paul Skenes is a strikeout machine having his shakiest stretch of the season, and the Cubs are the team built to make him pay for it.

Quick take:

• Pick: Cubs +1.5
• Why: Chicago’s lineup has feasted on Pittsburgh all year, and Skenes has posted a 4.93 ERA over his last seven starts
• The number to watch: Pete Crow-Armstrong’s .292 average and 19 home runs against a Pirates staff he’s already torched multiple times this season

Chicago rolls into PNC Park at 58-45, sitting second in the NL Central and still chasing a red-hot Milwaukee club, while Pittsburgh sits at 53-51 in fourth place. The Pirates have been better than their record most weeks thanks to Skenes, but this particular series has been lopsided in the Cubs’ favor — Chicago has won three of the four meetings between these two clubs this season, including a 7-2 win and a 10-4 blowout in late May.

Saturday night’s pitching matchup is the headline. Skenes has 130 strikeouts in 108.1 innings, fourth-most in the National League, and his 1.02 WHIP still ranks fifth among NL starters. But the surface numbers hide a real second-half stumble — over his last seven outings he’s 2-3 with a 4.93 ERA, a sharp step down from the sub-2.00 ERA ace who nearly won back-to-back Cy Youngs.

Why the Market Still Trusts Pittsburgh

Books have Pittsburgh as a moneyline favorite at home, priced around -122 to -132 depending on the shop, with Chicago sitting in the +104 to +112 range as the road underdog. The total sits between 8 and 8.5. Anyone shopping for the best number should check a DraftKings promo code before locking in a side, since line shopping matters more on a game this close. That line still reflects Skenes’ name value and PNC Park’s pitcher-friendly reputation more than his actual results the last month, and it’s created a spot where the Cubs’ plus-money price looks like real value against a struggling ace.

Crow-Armstrong and a Lineup That Won’t Let Up

Pete Crow-Armstrong has been the best player on the field in this series all year, hitting .292 with 19 home runs, 53 RBIs and 24 stolen bases, and he’s shown a knack for making Pittsburgh’s pitching staff look ordinary. Dansby Swanson has 16 homers and 58 RBIs of his own, and Saturday’s props already have the market leaning toward him delivering another run driven in — he’s an odds-on bet to clear 0.5 RBIs, and so is Carson Kelly further down the order.

Skenes has a 4.93 ERA in his last seven starts, nearly a run and a half higher than his three-year career mark of 2.35.

Other Game Picks

• Astros vs. White Sox Prediction: Sean Burke’s Command Tips the Scale at Rate Field
• Blue Jays vs. Red Sox Prediction: Toronto’s Season-Series Mastery Meets a Depleted Boston Rotation (July 25, 2026)
• Braves vs. Orioles Prediction: Grant Holmes and Atlanta’s Deep Lineup Are Worth the Plus Money at Camden Yards
• Yankees vs. Phillies Prediction: Cam Schlittler’s Quick Turnaround Looms Over Saturday’s Citizens Bank Park Rematch

That drop-off matters against a Cubs offense that’s shown zero fear of him or this Pittsburgh staff this season. Chicago is 6-3 against the spread in Matthew Boyd’s starts — though he’s not on the mound Saturday — and the larger trend of Chicago hitting well as an underdog holds up. The Cubs have won 15 of 28 games this year when priced as the moneyline dog, a 53.6% clip that’s well above break-even.

Imanaga isn’t dominant right now either, sitting at 5-8 with a 4.17 ERA, but he’s been sneaky effective of late — a 3.79 ERA over his last seven turns, including a strong 6.1-inning, two-run outing against San Diego. He doesn’t need to outduel Skenes here; he just needs to keep Pittsburgh’s lineup in check long enough for Crow-Armstrong and company to do the rest.

Prediction and Best Bet

This shapes up as a tighter game than the moneyline suggests, with Pittsburgh’s home field and Skenes’ name recognition doing more work in the line than his recent form justifies. The Cubs have the better all-around roster and a real recent track record against this specific Pirates team, and getting a run and a half of cushion is too good to pass up.

Mon, Sep 7 • 2:11 PM	Spread	Money	Total
Chicago Cubs	+1.5 (-207)	+115	O 8.5 (102)
Milwaukee Brewers	+1.5 (-210)	-124	U 8 (-104)

The pick:

1. Prediction: Cubs 5, Pirates 4
2. Best Bet: Cubs +1.5

Betting the moneyline is playable too if the price stays plus-money, but the run line offers the safer, more repeatable value on a night Skenes looks more hittable than his career numbers suggest.