The Chicago Cubs come in as a significant underdog as they face Paul Skenes and the Pittsburgh Pirates on Thursday night.
I’m backing Chicago to squeeze out just enough runs to get a win over the Pittsburgh ace in my Cubs vs. Pirates predictions.
Read on to get my free MLB picks for Thursday, May 28.
Who will win Cubs vs Pirates today: Cubs moneyline (+146)
Paul Skenes is coming off the roughest two-game stretch of his young career, allowing nine earned runs in 10 innings of work in two losses for the Pittsburgh Pirates.
Skenes has seen opponents square up more of his pitches than ever, with 32.7% of batted balls landing in the Launch Angle Sweet Spot this season.
The Chicago Cubs have been incredibly streaky this year, but are a fundamentally strong offensive squad, averaging 4.73 runs per game and posting a .725 OPS.
I’m backing Chicago to win this game as long as I can get a premium of +140 or more.
COVERS INTEL: The Cubs are raking against Skenes’ bread-and-butter pitch – the four-seam fastball – pulling it in the air 21.3% of the time against right-handed pitchers.
Cubs vs Pirates Over/Under pick: Under 7.5 (-110)
Even when Skenes struggles, it hasn’t been enough to hit the Over. The Pirates have played to totals of seven runs or less in five of his last six starts, as their ace keeps them in games even when the offense flounders.
While Colin Rea (4-3, 4.83 ERA) has struggled a bit this year, he has put up a strong 32.2% chase rate, which will play well against a Pirates team that ranks third-worst in whiff percentage this year at 27.5%.
I’m taking the Under at 7.5 runs if we can get the standard -110 odds or better.
- ML/RL bets: 9-14, -5.98 units
- Over/Under bets: 7-14, -7.53 units
Cubs vs Pirates odds
- Moneyline: Chicago +146 | Pittsburgh -161
- Run line: Chicago +1.5 (-142) | Pittsburgh -1.5 (+129)
- Over/Under: Over 7.5 (-103) | Under 7.5 (-112)
Cubs vs Pirates trend
The Pirates have hit the Under in each of Skenes’ last four starts. Find more MLB betting trends for Cubs vs. Pirates.
How to watch Cubs vs Pirates and game info
| Location | PNC Park, Pittsburgh, PA |
| Date | Thursday, May 28, 2026 |
| First pitch | 6:40 p.m. ET |
| TV | MARQ, SNP |
| Cubs starting pitcher | Colin Rea (4-3, 4.83 ERA) |
| Pirates starting pitcher | Paul Skenes (6-4, 3.00 ERA) |
Cubs vs Pirates latest injuries
Cubs vs Pirates weather
Odds are correct at the time of publishing and are subject to change.
Not intended for use in MA.
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