Chicago Cubs vs Pittsburgh Pirates Prediction, Odds and Picks for Today, 05/26/26

The Chicago Cubs continue to fall further behind in the NL Central standings after dropping their 9th straight game following a 2-1 loss to the Pittsburgh Pirates on Monday. Today, the Cubs will look to snap their 9-game losing streak as they hand the ball over to the lefty Jordan Wicks, who is set to make his first start of the season in hopes to bolster an injury-plagued Cubs rotation. Last season, Wicks went 0-1 with a 6.28 ERA. For the Pirates, they’ll look to keep things rolling with Braxton Ashcraft who is 3-2 with a 2.89 ERA this season. Ashcraft has been terrific as of late, going 2-0 with a 1.91 ERA and 26 strikeouts in his last four starts.

Chicago’s problems extend beyond just the offense. Over their last 10 games, the Cubs have committed eight errors defensively while averaging only 3.4 runs per game and batting .200 in that span. Pittsburgh hasn’t exactly been explosive offensively either, but the Pirates are averaging 3.8 runs per game while hitting .245 during that same stretch. There are a lot of unknowns for Chicago entering this matchup. Wicks is making his season debut, the offense continues to struggle badly, and the defense hasn’t been reliable enough to support inconsistent pitching. Meanwhile, Ashcrat has been dominant lately and continues to give Pittsburgh quality innings nearly every time he takes the mound. The Pirates have also been a much stronger team at home this season, batting .274 at PNC Park, while the Cubs are hitting just .230 on the road. With Pittsburgh holding advantages both offensively and on the mound, the Pirates are in a stronger position to keep rolling while Chicago’s losing streak reaches double digits. 

Cubs vs Pirates prediction: Pirates ML  (-130) at the time of publishing. Playable to (-145).

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