Chicago Cubs at Pittsburgh Pirates – MLB Pick 9-21-20

Well, folks, after an eight-week whirlwind of a regular season so far, we hit the final week of the regular season today. And while most of the division races are locked up at this point, or close to it, we do have ample drama unfolding in the next several days as the season winds to a close.

In the American League, the Rays, Yankees, White Sox, Twins, and Athletics all have playoff spots locked up, and while technically the division races are not over, it is looking highly likely that the White Sox, Rays, and Athletics will be your division champs. The Seattle Mariners are hoping to catch the Houston Astros for second place in the AL West, and the Cleveland Indians and Toronto Blue Jays look like your AL wild card teams.

Over in the National League, only the Dodgers and Padres have playoff spots clinched, but the Atlanta Braves have a three-game lead in their division, the NL East, and the Chicago Cubs are up three and a half games in the NL Central. Second place and the wild card spots are wide open in the NL, and if the season were to end today, the Marlins, Cardinals, Phillies, and Reds would be playing in the postseason.

But the Brewers and Giants are both just a half of a game back, and the Mets and Rockies still have sweat as well. It should be an exciting end to the regular season and even more exciting once the playoffs kick off next week. For today’s free daily betting pick, we will head to the National League, where the Chicago Cubs will look to clinch their division title in a series with the Pirates.

Chicago Cubs (31-22) at Pittsburgh Pirates (15-38)

The Chicago Cubs have their sites set on the National League Central Division title this week as they close out the regular season in game one of a four-game series with the Pittsburgh Pirates. The Cubs are three and a half games ahead of the second-place St. Louis Cardinals, and four and a half games ahead of both the Cincinnati Reds and Milwaukee Brewers.

For Pittsburgh, the Pirates could win out this week in the regular season’s final week of play, and still likely finish with the worst record in the Major Leagues. It has been a very disappointing season for the Pirates, and they have lost twelve out of their last thirteen games as they stumble to the finish line. This series marks the final homestand of the year for Pittsburgh.

Starting tonight for the Cubs is Jon Lester (2-2 4.91 ERA), and for the Pirates, it is JT Brubaker (1-2 4.79 ERA). The game total over/under is set at eight and a half runs. The Cubs are -150 road favorites. First pitch is scheduled for 4:05 PM PST from PNC Park in Pittsburgh.


  • Pittsburgh Pirates +1.5 (-127)
  • Chicago Cubs -1.5 (+107)
Money Line:

  • Pittsburgh Pirates (+135)
  • Chicago Cubs (-150)
  • Total Runs:

    • Over 8.5 (-108)
    • Under 8.5 (-113)

    Chicago Cubs

    The Chicago Cubs had a shot at slamming the door shut in the NL Central Division race this weekend in their series against the Minnesota Twins, but just couldn’t take care of business, dropping two out of three to Minnesota. The Cubs had won four straight games heading into the series with Minnesota, and after winning game one to extend their winning streak to five in a row, they lost games two and three, meaning they still have work left to do this week if they want to take home the NL Central crown.

    The Cubs lineup completely no-showed against Minnesota, as they managed to score just two total runs in the three games. If it weren’t for Kyle Hendricks’s monumental performance in game one of the series, the Cubs probably would have gotten swept. Chicago had just twelve total hits in the 27 innings against the Twins, and the Cubs have to find a way to turn the bats back on before the playoffs start next week.

    Jon Lester (2-2 4.91 ERA)

    It has been a rollercoaster ride of a season for Jon Lester. After his first three starts, he looked like an ace. Then he had a five-start stretch where he got blown out in four of them. And in his last two starts, he has things going in the right direction again, as he has pitched a combined eleven innings and has allowed just two earned runs.

    Interestingly enough, Lester has had far more success on the road this season than he has at home. In Chicago, he is 0-2 with a 7.88 ERA in five starts. On the road, he is 2-0 with a 2.30 ERA in five starts. He has yet to allow a single home run on the road this season. He has two starts against the Pirates this year, and in one of them, he was stellar, allowing just one run in six innings of work, and in the other, he got lit up for five runs in 5.1 innings. The Cubs did win both games, though, despite Lester’s lack of consistency.

    Pittsburgh Pirates

    I won’t be wasting a lot of breath on the Pirates today. They have been awful all season long, and they are playing their worst baseball of the season right now. The Pirates have a unique combination of futility in that they can’t score runs, and they give up way too many. Pittsburgh is dead last in the majors in runs scored, on-base percentage, home runs, and slugging. Against the Cubs this year, they are 1-5.

    JT Brubaker (1-2 4.79 ERA)

    JT Brubaker has been able to put together some solid stats in the Minor Leagues in the last two years, and after missing most of last season with an injury, is finally healthy and got his shot at the show this season. Brubaker started his season pitching out of the Pittsburgh bullpen and was quickly promoted to the starting rotation. And while he has had some flashes of looking respectable, the overall body of work has not been great.

    In his seven starts, he has allowed multiple runs in six of them and has pitched five or fewer innings in all but two outings. He was a little bit better in his last start, though, as he has pitched into the sixth inning and had the best start of his career, allowing just one run. But the Pirates still lost the game, and Brubaker was charged with a hard-luck loss.

    Who Do I Like?

    When I first looked at this game, I thought that this might be a nice spot for a home dog play. JT Brubaker looked solid in his last start, and Jon Lester has been super inconsistent. But as I started to break this game down, I realized that even when Lester isn’t great, the Cubs still usually win. And when Brubaker had the best outing of his short career in his last start, the Pirates still lost.

    The Cubs are very flawed, that can’t be denied at this point. But the Pirates are the worst team in the Major Leagues by a wide margin. Even when they play decent in a game, they manage to find a way to lose games. I didn’t really want to lay -165, where the Cubs opened up at, but now that the public has backed the Pirates, the line has dropped fifteen points, and I don’t mind laying a little wood in a good spot, and will thank the public for giving me a discount.

    The Bet

    Lester seems to have gotten things back on track recently, and his production on the road can’t be ignored. The Pirates are last in basically every major hitting category, and if Lester has even mediocre stuff tonight, he is going to have a lot of success. JT Brubaker might be OK tonight, but he isn’t a guy that is going to get you a lot of innings, meaning that the Cubs are going to get to feast on the bad Pirates bullpen at some point.

    I think that the Cubs will find a way to score enough runs to win this game. The struggles at the plate are certainly concerning, but I just don’t see Lester and the Cubs giving up many runs to this dreadfully bad Pirates lineup, so a couple of runs should be enough to give Chicago the win. So, I’ll lay a little wood and back the Cubs in this one. Give me the Chicago Cubs laying -150 on the road tonight from PNC Park!

    The Bet: Chicago Cubs -150

    My Pick
    Chicago Cubs
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    Jason Gray / Author

    Jason is a true Las Vegas insider as he has called the sports betting capital of the world his home for sixteen years. Jason started out his career in gaming by running the biggest poker tournaments in the world and managing some of the biggest sportsbooks on the strip. Jason has transitioned out of casino operations and has been covering sports betting for the sports geek for just over two years. His main focus is on baseball, college basketball, and the NFL