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Chi. Cubs (29-25) at Pittsburgh (28-26)
- When: May 26 2026, 6:40 PM
- Where: PNC Park, Pittsburgh
- TV: Marquee Sports Network
Chi. Cubs vs Pittsburgh MLB Preview & Pick
Moneyline: Pittsburgh -128
Runline: Pittsburgh -1.5 (+165)
Total: 8.0
Chicago Cubs Betting Outlook
The Cubs head into Pittsburgh searching desperately for answers after dropping nine straight games, their longest losing streak of the season. What makes this stretch even more frustrating for bettors is how inconsistent Chicago has looked offensively. This is still a team that managed two separate 10-game winning streaks earlier in the year, but lately the bats have completely disappeared at critical moments.
Jordan Wicks gets the call Tuesday night in his season debut after being activated from Triple-A Iowa. The left-hander missed time earlier this season because of elbow inflammation and now enters a difficult spot against a Pirates lineup that continues improving at home.
Wicks has shown flashes during his young career, especially against Pittsburgh where he owns a 1.80 ERA in one previous start. Still, expecting him to immediately stabilize an injury-riddled rotation may be asking a lot considering he posted a 6.28 ERA across limited work earlier this year.
The biggest issue remains the Cubs offense. Outside of Michael Busch’s solo homer Monday night, Chicago again struggled to generate meaningful production. Over the past week, the lineup has repeatedly stranded runners while failing to deliver with men in scoring position.
Busch continues battling through the slump and remains one of the few consistent threats in the middle of the order. But until Chicago starts producing early offense, this team becomes difficult to trust against quality pitching.
The Cubs also enter Tuesday carrying enormous pressure mentally. Once losing streaks stretch this long, every inning suddenly feels heavier for both players and bettors backing them.
Pittsburgh Pirates Betting Outlook
The Pirates continue quietly building momentum behind excellent starting pitching and improved power numbers. Monday’s 2-1 victory perfectly summarized the formula Pittsburgh has used successfully most of the season: score first, trust the pitching staff, and let the bullpen finish games late.
Braxton Ashcraft has become one of the most reliable surprises in the Pirates rotation. The right-hander enters with a 2.89 ERA and continues delivering quality outings nearly every time he takes the mound. Over his four starts in May, Ashcraft owns a dominant 1.91 ERA while consistently working deep into games.
His most recent outing against St. Louis may have been his sharpest yet. Ashcraft struck out nine hitters across seven innings while allowing just one run. More importantly for bettors, he continues limiting walks and avoiding major innings.
Pittsburgh already handled Ashcraft’s earlier matchup against Chicago this season, where he struck out nine Cubs while allowing just one earned run. That success matters entering another meeting against a struggling lineup low on confidence.
The Pirates offense has also taken a noticeable step forward compared to last season. Henry Davis delivered the game-winning homer Monday, and Pittsburgh’s offseason additions have significantly boosted overall power production.
The numbers strongly favor Pittsburgh whenever they score first, and facing a pitcher making his season debut gives the Pirates an excellent opportunity to attack aggressively early.
MLB Prediction & Betting Angle
Chicago’s losing streak eventually ends, but this matchup still favors Pittsburgh heavily because of Ashcraft’s recent form and the Cubs’ offensive collapse.
The Pirates should control tempo early while their pitching staff continues frustrating Chicago hitters.
Final Score: Pirates 5, Cubs 2
Lean: Pittsburgh -1.5 (+165)
Total: Under 8.0 (-110)
- MLB Baseball Odds source: Bovada Sportsbook
- Get real-time live scores & latest betting odds here!
