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Cubs vs Pirates MLB Parlay Picks for Monday, August 26

Cubs vs Pirates MLB Parlay Picks for Monday, August 26 article feature image
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Daniel Shirey/MLB Photos via Getty Images

On Monday night, the Chicago Cubs will take on the Pittsburgh Pirates in an NL Central clash. Both teams enter the series having won six of their last 10 games. However, they still find themselves on the periphery of the NL wild-card race, with the Cubs 5.5 games back and Pirates are eight games back.

Jameson Taillon will get the start for the Cubs and will be opposed by Pittsburgh's Mitch Keller. Read on for my same-game parlay for tonight’s game.

Alex Hinton's Cubs vs Pirates MLB Parlay Picks for Monday

  • Mitch Keller Over 1.5 Walks (-135)
  • Bryan De La Cruz Over 0.5 Strikeouts (-225)
  • Cody Bellinger Over 1.5 Total Bases (+115)
  • Ian Happ Over 1.5 Total Bases (+120)

Parlay Odds: +800 (DraftKings)

Remember to bet responsibly — this is a long shot for a reason.

Cubs Logo
Monday, Aug 26
6:40pm ET
SportsNet PT
Pirates Logo
Mitch Keller Over 1.5 Walks (-135)
DraftKings Logo

Mitch Keller is coming off one of his best starts of the season in Texas, having struck out nine and scattering three hits in seven scoreless innings. He did not walk a batter in that outing, but that snapped a streak of six consecutive starts with two walks or more. Some of those came in longer outings, but in four of those starts, he walked two batters in five innings or less.

Keller last faced the Cubs in May, when he issued three walks in six innings. He has walked two or more in three of his last five starts against the Cubs. The Cubs are fifth in walk rate against right-handed pitchers this season. Six hitters in Chicago's lineup have an 8% or higher walk rate against right-handers, with three of them being 11% or higher. I expect at least two of them to work a free pass against Keller tonight.

Cubs Logo
Monday, Aug 26
6:40pm ET
SportsNet PT
Pirates Logo
Bryan De La Cruz Over 0.5 Strikeouts (-225)
DraftKings Logo

Bryan De La Cruz had 18 home runs with the Marlins this season. The Pirates acquired him at the trade deadline to add more punch to their lineup, but thus far he has not been able to get on track. In 20 games with Pittsburgh, De La Cruz does not have a home run yet and is hitting just .221 with a .507 OPS. However, his propensity for striking out is one thing that has carried over.

De La Cruz has a 27.2% strikeout rate this season, which slightly increases to 28.1% against right-handers. He has 145 strikeouts in 125 games this season, with at least one in 99 of them. Since joining the Pirates, De La Cruz has struck out once in 18 of 20 games.

Jameson Taillon is not a huge strikeout artist ,with 101 in 126 2/3 innings this season. However, he has fanned De La Cruz twice in four plate appearances. With an 80% hit rate for the season and 90% as a Pirate, one De La Cruz strikeout is a great piece for this parlay.

Cubs Logo
Monday, Aug 26
6:40pm ET
SportsNet PT
Pirates Logo
Cody Bellinger Over 1.5 Total Bases (+115)
DraftKings Logo

Two Cubs who have enjoyed a lot of success against Keller are Ian Happ and Cody Bellinger. Happ is 9-for-25 (.376) with two doubles, three home runs, seven runs batted in and a 1.267 OPS lifetime against Keller. He enters tonight's game with six hits, including three doubles and a home run, in his past four games. As a result, he has hit this line in three of his past four games.

Meanwhile, Bellinger had been hitting a lot of singles until recently. However, he has a double in four of his past six games. He is also 4-for-11 (.364) against Keller, and three of those hits were doubles. He is hitting .296 on the road and .288 in night games this season.

Manager Craig Counsell has alternated Bellinger and Seiya Suzuki hitting third and fourth in the lineup recently, while Happ has been the primary leadoff hitter. Both Happ and Bellinger should have four plate appearances to clear this line and possibly a fifth if the Cubs' offense gets going tonight.

Cubs Logo
Monday, Aug 26
6:40pm ET
SportsNet PT
Pirates Logo
Ian Happ Over 1.5 Total Bases (+120)
DraftKings Logo
About the Author
Alex Hinton began sports betting toward the end of 2018. He got his first job in the industry with The Action Network in 2021. Hinton joined Action as a College Sports Contributor, but he now also covers the MLB and NBA. Before joining Action, Hinton covered Michigan Athletics for GoBlueWolverine. 

Follow Alex Hinton @AlHinton23 on Twitter/X.

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