Ed Scimia
• Betting Analyst
17+ years betting experience
Updated:
May 28, 2026 , 03:43 PM ET
• 4 min read
The Cubs will take full advantage of Paul Skenes, who hasn’t looked like himself in recent outings.
Photo By – Reuters Connect. Chicago Cubs pitcher Colin Rea (53) throws against the Atlanta Braves in the first inning.
The Chicago Cubs come in as underdogs against Paul Skenes and his Pittsburgh Pirates on tonight.
However, my Cubs vs. Pirates predictions expect them to pull off the upset, with the reigning Cy young winner not playing at his best lately.
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.
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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.
Ed Scimia’s 2026 Transparency Record
- 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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Ed Scimia has been writing about the gaming industry for over 15 years. He graduated from Syracuse University with degrees in Magazine Journalism and Political Science in 2003, and has covered major gambling events like the World Series of Poker in his career. Since joining Covers in 2022, Ed has offered his sports betting analysis primarily on MLB, NFL, college football, and college basketball games, but is willing to take on any sport.
His betting strategy focuses more on finding line value based on deviations from the market rather than traditional handicapping, primarily shopping between DraftKings, FanDuel, and Fanatics in his home state of Connecticut, though he’s not afraid to do deep game analysis to find profitable bets at any book.
Outside of gambling, Ed is an avid curler who competes in mixed doubles on the World Curling Tour and runs a popular curling YouTube channel, Chess on Ice. That experience has come in handy during the Olympics, when he has proven to be a successful curling bettor as well.
Ed’s advice to new bettors is to always open multiple sportsbook accounts and check the odds at each before placing any bet. Successful sports betting is about consistently beating the closing line value, which requires finding spots where one book is offering odds far better than the rest of the market and jumping on those opportunities.
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