Chicago Cubs at Cincinnati Reds – MLB Pick 7-27-20

What a strange first weekend of action we had to kick off the 2020 Major League Baseball season. After seeing several +200 or bigger underdogs win on Saturday, the carnage continued on Sunday, as we saw the Giants, Orioles, Tigers, and Marlins all pickup wins as heavy betting underdogs. A quick glance at the standings shows us the Tigers, Orioles, Marlins, and Rockies all tied for first place in their respective divisions.

Entering the season, most expected the bad teams to be really bad, and the good teams to be great, but if the first weekend was any reminder, anything can happen in baseball with a short sample size. Did you bet on a Marlins vs. Orioles World Series? Yeah, neither did I, but after seeing a wild and crazy first weekend of play, this could end up being an anything could happen regular season! For today’s daily betting pick, we will head to Cincinnati, where the Reds host the Chicago Cubs.

Chicago Cubs (2-1) at Cincinnati Reds (1-2)

The Cincinnati Reds are reeling after losing two out of their first three games of the season, against a Detroit Tigers team that most expected to be amongst the worst team in the game. Cincy will try and get things turned back around tonight as they host the Chicago Cubs in game one of a four-game series. For the Cubs, they started their season out by winning two out of their first three games against the Milwaukee Brewers and would love to take advantage of a Reds team that is banged up and not playing well tonight.

Starting tonight for the Reds is veteran Wade Miley (0-0 0.00 ERA), and for the Cubs, it is former ace, Jon Lester (0-0 0.00 ERA). The Cubs are -118 road favorites. The game total over/under is set at ten runs. First pitch is scheduled for 3:30 PM PST from Great American Ballpark in Cincinnati.


  • Chicago Cubs -1.5 (+133)
  • Cincinnati Reds +1.5 (-159)
Money Line:

  • Chicago Cubs (-118)
  • Cincinnati Reds (+105)
  • Total Runs:

    • Over 10 (-107)
    • Under 10 (-114)

    Chicago Cubs

    With all the upsets, the Chicago Cubs were one of the few teams that were favored this weekend that found a way to come away with a series win. The Cubs took two of three from Milwaukee, and they did it by locking the Brewers down on the mound. In game two, Chicago got beat up, allowing nine runs, but in games one and three, they allowed just one earned run total. Milwaukee hit just .175 against Chicago in the three-game set.

    While the bats weren’t hitting at that high of an average, they were hitting with a lot of power, as Chicago smashed six home runs, with Anthony Rizzo and Ian Happ both hitting two long balls. The NL Central seems to be completely up in the air, and whichever team finds a way to win these early divisional games is going to have a big head start on the rest of the division.

    Jon Lester (0-0 0.00 ERA)

    The days of Jon Lester being a top of the rotation type of guy look like they may very well be over. The former five-time All-Star has finished in the top ten of the Cy Young Award voting four times and has been one of the most consistent arms in the game for the last fourteen years, but struggled some last season and is closing in on 37 years old.

    Had this season not been cut short, he would have been a near-lock to win his 200th game in 2020. Not many guys are going to get you 200 wins anymore, and Lester will have a real shot at making the Hall of Fame for the major role he played in winning titles for both the Boston Red Sox and the Cubs. But last season, Lester struggled through one of the worst years of his career as he posted a 4.46 ERA in 31 starts.

    But it wasn’t all bad for Lester last year. He still showed spurts of being very good, as he had fourteen quality starts in 2019, he just wasn’t able to stay consistent. His 20 strikeouts against the Reds last year were the most he had against any team. The Cubs will need Lester to regain his 2018 form when he won 18 games with a 3.23 ERA, if they want a real chance at bringing home another World Series title to Chicago’s north side.

    Cincinnati Reds

    Yikes. Things have gone from bad to worse for the Cincinnati Reds in a hurry. Just a week ago, the Reds were a sexy dark horse pick to win the National League pennant and were legitimate threats to take home the NL Central Division crown. But then the season started, and they lost two out of three games to my pick for the worst team in the Major Leagues, the Detroit Tigers, and they woke up this morning to a couple of their best players hitting the IL.

    Mike Moustakas and Nick Senzel both were shut down this week with illness and join Matt Davidson on the injured list. That is three of the Reds everyday starters that they are going to have to play without in this series with the Cubs. A series that could have major playoff implications. Starting pitcher Anthony Desclafani is also out injured, and the Reds are suddenly playing very short-handed.

    Wade Miley (0-0 0.00 ERA)

    I wonder if Wade Miley has figured out how to stop tipping his pitches? Last year, Miley was pitching at a borderline Cy Young Award level through August, as he was 13-4 with a 3.06 ERA. Then opposing teams caught on to something about the way he was tilting his glove and started figuring out what he was going to throw. He finished the season by posting an ERA of nearly seventeen runs in September!

    Miley claims to have things figured out for 2020, but that has yet to be seen. And with the ragtag group of hitters in this lineup to support him, he needs to get back to be good again, and fast, if the Reds want to weather this early season storm and stay in the playoff hunt.

    Who Do I Like?

    No team was more disappointing this weekend than the Cincinnati Reds. Losing two of their best hitters this week is only going to make things even worse. I absolutely loved this Reds team coming into the season. But after seeing them get decimated by injuries, many of which are illness-related, telling me that more might be about to come as well, I will have to adjust my expectations of this team on the fly.

    I think Chicago will take advantage of this weekend lineup and win this game. Outside of Yu Darvish and reliever, Brad Wieck, the rest of this Cubs pitching staff has been really good. I expect them to shut down this weakened Reds lineup. Even if Miley finds a way to be good, the Reds bullpen has been awful, allowing seven earned runs in the 7th inning or later in the last two games, blowing leads both times.

    The Bet

    I much prefer to take underdogs than favorites when betting Major League Baseball. But when I see the Cubs only listed as small favorites, against a Reds team in free fall, that will be playing without several of their best players tonight, I see a lot of value in backing Chicago.

    I think Lester will be at least decent, and the Reds bullpen could get lit up again. So, I will do something I rarely do, and lay a little bit of wood on Chicago, and back the Cubs. Give me the Chicago Cubs as small road favorites tonight in game one against the Reds, laying -118!

    The Bet: Chicago Cubs -118

    My Pick
    Chicago Cubs
    Sub Categories:
    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

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