Cubs vs. Pirates Prediction, Odds, Probable Pitchers, Prop Bets for Monday, May 25

The midweek Cubs-Pirates series kicks off Monday afternoon as Chicago seeks to reverse an eight-game losing streak while maintaining a 29-24 record. The skid hasn't been just bad luck; the Cubs' offense has regressed, ranking 21st in wRC+ over the past 30 days, a contrast to the Pirates who sit ninth in the same metric. Ben Brown starts for Chicago after a rough previous outing against Milwaukee, where seven hits and three earned runs crossed the plate. In the betting column, the writer leans toward Brandon Lowe recording two or more hits at better-than-3-to-1 odds, citing his 47 hits and a .898 OPS this season and two multi-hit games in the last four.

Analysts frame the Pirates as slight home underdogs, suggesting they can exploit Chicago's offensive dip and capitalize early in the series. The game's odds fluctuate with updates, but the angle emphasizes Pittsburgh's improved form and the Cubs' need to stop the bleeding to avoid falling behind in the NL Central. The matchup tests momentum, with Pittsburgh aiming to climb above .500 as Chicago strives to steady itself. The article notes the quick turnaround as crucial in a tight division race.