MLB Picks Today: Best MLB Bets for Monday, August 26

MLB Picks Today: Best MLB Bets for Monday, August 26

This article is part of our MLB Picks series.

MLB Best Bets Today: Pittsburgh Pirates vs. Chicago Cubs

Don't miss out on the top sportsbook promos from your favorite sports betting apps to ensure you get the most out of your sports betting experience. This BetMGM bonus code awards new users a first-bet bonus worth up to $1,500.

Pittsburgh Pirates vs. Chicago Cubs

The Chicago Cubs are taking on the Pittsburgh Pirates in the first game of a three-game series between these division rivals. Both teams had aspirations of making the playoffs when the season started but those aspirations have seriously dwindled for both sides. The Cubs are one game below .500 at 65-66 this season and 5.5 games out of a Wild Card spot. They are much better at home (36-29) this season but have struggled on the road (29-37). They have played an incredible amount of games against teams with winning records, though, and are 41-47 in those games. That means they are 24-19 against teams with losing records. That also means the Cubs have played just 43 of their 131 games this season against teams with a losing record. That's the second-fewest games against losing teams behind only the Rockies (40). The Pittsburgh Pirates got off to an amazing start this season and looked like they were ready to compete for a playoff position, but they have had too many down stretches. They went on a very long cold streak around May that killed them. They also recently went on a 10-game losing streak (Padres at home, Dodgers on the road, Padres on the road). They are 62-68 this season and have done a lot of it without Jared Jones. This team is eight games out of a Wild Card spot, so they are likely missing the playoffs, but they are on the right track and should be legitimate contenders to win the division next season.  They are just 32-33 at home this season and 33-48 against teams with a winning record.

Use this DraftKings promo code to earn $200 in bonus bets and check out the latest MLB odds before placing your bets.

Jameson Taillon has struggled lately with a 5.73 ERA in August. He has just two quality starts in his last six with three straight poor starts on the road. He has faced the Pirates once this season, allowing three runs in 4.2 innings, although that was back in May. He is facing one of his old teams, so there could be a bit of a revenge or nostalgia factor there. Mitch Keller had been struggling pitching seven scoreless innings against the Rangers in his last start. He has made three straight road starts and is much better at home, going 5-2 with a 2.58 ERA. He has faced the Cubs once this season, allowing two runs in six innings on the road. The Pirates are 4-3 against the Cubs this season but they lost the only series in Pittsburgh they played. They also haven't played since May.

The Cubs have been hitting righties much better than the Pirates lately. They are ranked 11th in the league in wOBA against righties since the trade deadline while the Pirates are ranked 28th.  The Pirates are also still missing Andrew McCutchen, which is a tough blow. The Cubs have sneakily been playing great baseball for a while now, going 13-8 since the trade deadline, the sixth-best record in the league. They are 4-4 on the road and are coming off a series win over the Marlins. The Pirates are 7-15 since the trade deadline and 6-7 at home in that time. They are also coming off a series win but against the Reds. The bullpens are going to be a major factor here. The Cubs have the seventh-best bullpen in the league since the trade deadline with a 3.31 bullpen ERA while the Pirates are ranked 12th. However, the Cubs will have their entire bullpen rested and ready while the Pirates could be without multiple relievers. Kyle Nicolas and Jalen Beeks have both pitched two days in a row and could be unavailable. Hunter Stratton was also just added to the injured list (IL) and Aroldis Chapman and Dennis Santana have pitched two of the last three days.  David Bednar is the only rested reliever. He has a 5.56 ERA on the season.

Best MLB Bet Today

Cubs ML (-102 DraftKings Sportsbook)

RotoWire Community
Join Our Subscriber-Only MLB Chat
Chat with our writers and other RotoWire MLB fans for all the pre-game info and in-game banter.
Join The Discussion
ABOUT THE AUTHOR
John Bollman
I am a data scientist and baseball analyst who grew up in Bethesda, Maryland before I moved to South Florida about five years ago. I went to Tulane University in New Orleans for both undergraduate and graduate school, and worked for the Tulane Baseball team as a Quantitative Analyst while working towards my Masters degree in Biostatistics and Data Science. I worked for the Toronto Blue Jays in their Player Development and High Performance departments out of graduate school and I am the founder and owner of my company Baseball with Bollman.
Farm Futures: Rookie Infielder Targets
Farm Futures: Rookie Infielder Targets
Collette Calls: Does Controlling the Running Game Really Matter?
Collette Calls: Does Controlling the Running Game Really Matter?
Farm Futures: Rookie Pitcher Targets
Farm Futures: Rookie Pitcher Targets
Offseason Deep Dives: Sean Manaea
Offseason Deep Dives: Sean Manaea
RotoWire Roundtable: 2025 Fantasy Baseball Top-300 Rankings
RotoWire Roundtable: 2025 Fantasy Baseball Top-300 Rankings
The Z Files: My New Approach to the Roundtable Rankings
The Z Files: My New Approach to the Roundtable Rankings