Chicago Cubs at Pittsburgh Pirates – MLB Pick 9-22-20

Sometimes you just have to pick the low hanging fruit and snatch up some free money. I am never against the path of least resistance, and while I pride myself on being a sharp handicapper, sometimes you can find spots that aren’t all that hard to figure out. That was the case yesterday in the game between the Chicago Cubs and the Pittsburgh Pirates.

Jon Lester has had his fair share of ups and downs this year, but he had been pitching well in his previous two starts, and I expected to again be very good against a Pirates team that is dead last in nearly offensive category in the game this year. I quipped that even if he had just mediocre stuff, it would be enough to shut down the weak-hitting Pirates.

Throw in the fact that the Cubs are a first-place team, and the Pirates are the worst team in baseball, that is not at all hyperbole, as they have the most losses, fewest wins, and worst run differential in MLB; I felt that the Cubs should have been heavily favored. Instead, I got to back Chicago at a reasonable -150, after the public shifted the line towards the Pirates.

I didn’t see this game as an overly competitive matchup, and when all was said and done, the game was indeed not remotely competitive. Lester shined, as he pitched six shutout innings, and while the Cubs bats were again a little concerning, Chicago took an early lead and coasted to a 5-0 victory.

The Cubs now hold a four and a half-game lead in the central over both the St. Louis Cardinals and the Cincinnati Reds and are a win or two away from clinching. For today’s free daily betting pick, will stay right here in Pittsburgh and break down the action in game two between the Cubs and Pirates.

Chicago Cubs (32-22) at Pittsburgh Pirates (15-39)

The Chicago Cubs are looking for back to back wins over the Pittsburgh Pirates tonight in game two of a four-game series. The Cubs are oh so close to locking up the National League Central Division title, and a win tonight would go a long way towards clinching. The Cubs are 9-4 in their last thirteen games, as they are finishing the regular season strong.

For Pittsburgh, the Pirates are in free fall as they have now lost five straight games and thirteen out of their last fourteen. In nearly every way you can measure a baseball team’s level of success, the Pirates are the worst team in the game. Pittsburgh can’t wait for the season to end this weekend.

Starting for the Cubs tonight in game two is veteran Jose Quintana (0-0 6.00 ERA), and for the Pirates, it is Steven Brault (1-3 4.04 ERA). The game total over/under is set at eight and a half runs. The Cubs are -145 road favorites. First pitch is scheduled for 4:05 PM PST from PNC Park in Pittsburgh.


  • Pittsburgh Pirates +1.5 (-122)
  • Chicago Cubs -1.5 (+104)
Money Line:

  • Pittsburgh Pirates (+125)
  • Chicago Cubs (-145)
  • Total Runs:

    • Over 8.5 (-121)
    • Under 8.5 (+100)

    Chicago Cubs

    The Chicago Cubs lineup has really been struggling in the last several weeks. They have a slew of star hitters, but they just aren’t producing right now. Javier Baez is hitting .206, Anthony Rizzo is hitting .213, Kyle Schwarber is hitting .198, and Kris Bryant is hitting an abysmal .195. But the lack of run production hasn’t hurt them, as they are pitching really well and still winning a lot of games.

    In the last two weeks, the Cubs have four shutout victories. Your lineup doesn’t need to score many runs if their pitching staff shuts the other team out. In the month of September alone, the Cubs have held opposing teams to three runs or fewer eleven times already. Even embattled closer Craig Kimbrel is figuring things out, as he hasn’t allowed a run in his last six appearances, after posting an ERA approaching double-digits early on this season.

    Jose Quintana (0-0 6.00 ERA)

    The Cubs are already pitching their brains out and welcomed Jose Quintana back to the rotation two weeks ago. Quintana missed most of the season with a cut on his hand and made his first start of the year on 8/25. The Cubs have chosen to move him along slowly, as he has pitched just three innings in each of his two starts. After a tough outing in his first start, he looked sharp in his last one, and Chicago would love to have him back to pitching at his normal level of production by the time the playoffs start.

    Quintana has been one of the most consistent starters in the game for the last decade, as four times he has pitched over 200 innings in a season, and in the last two years for the Cubs, he has pitched 170+ innings in both seasons and won thirteen games each year. He probably won’t be part of this Cubs playoff rotation as guys like Alec Mills, Yu Darvish, Kyle Hendricks, and Jon Lester are pitching really well, but he gives Chicago a lot of flexibility on the mound that they will love to have in the extended postseason.

    Pittsburgh Pirates

    In yesterday’s pick, I said I wasn’t going to waste much time telling you how bad the Pirates are this year, and I won’t waste your time with that today either. The Pirates are bad, really bad, and right now, they aren’t even competitive in most games. The Pirate’s current winning percentage of .278 has them as one of the worst teams in MLB history in terms of winning percentage.

    If the Pirates don’t manage to win at least one more game this season, they will post the third-worst winning percentage in modern Major League Baseball history, with the equivalent of 120 losses in a full 162-game season. If you thought that the Pirates were just a bad team, you were wrong, they are a historically bad team.

    Steven Brault (1-3 4.04 ERA)

    When you are playing for a team that never wins, it’s no shocker that you don’t have many wins on the year. So, despite Steven Brault being decent at times, he has been doing a lot of losing. That one win he does have? That came in his last start when he pitched a complete game and allowed just one run on two hits against the St. Louis Cardinals. Before that stellar outing, the Pirates had lost eight out of Brault’s nine starts.

    Who Do I Like?

    It was really hard to predict Steven Brault to pitch a complete game in his last start. He had never pitched all nine innings in a game before in his five-year big-league career, and this season, before that start, his longest outing of the year was just five innings. He was averaging just under three innings an appearance. It was the definition of a fluke.

    Major League Baseball is all about teams and players regressing back towards the mean. After seeing Steven Brault inexplicitly pitch a gem in his last start, I expect him to give some of that back tonight against the Cubs, even though they aren’t hitting very well at the moment. In his four starts before last week, he had allowed three runs, four runs, and four runs in three of them, spanning just 11.2 total innings. That is the type of performance I expect out of him tonight at home. He won’t be in the game long, and he will give up at least a couple of runs before they yank him out of the game.

    The Bet

    Look, this is a mismatch on every possible level. Similar to last night’s game between these two teams, I just don’t see the Pirates being competitive. They have very clearly given up on the season at this point. The Cubs have beaten them in six out of their seven games this year, and I think Chicago takes advantage of the weak competition and sweeps the Pirates in this series and locks up the NL Central Division title along the way.

    Quintana probably only pitches four or five innings, but the Cubs bullpen has been really great recently, and we have seen that the Pirates just can’t hit the baseball. Steven Brault did pitch three shutout innings against the Cubs earlier this year, but last year, he made three starts against Chicago and got hammered to the tune of an 0-2 record and a 10.66 ERA.

    Expect Chicago to continue to dominate this series and win this game easily. This is another spot where I will pick the low hanging fruit and snatch up some free cash with little to no sweat. Give me the Chicago Cubs tonight, laying -145 on the road in Pittsburgh.

    The Bet: Chicago Cubs -145

    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