Milwaukee Brewers at Chicago Cubs – MLB Pick 8-16-20

Yesterday, the Milwaukee Brewers were road favorites against the Chicago Cubs, really for one main reason, the starting pitching matchup. Milwaukee was starting Adrian Houser, who had pitched really well to start the season, and the Cubs were going with Colin Rea, a guy that hadn’t pitched in the big leagues since 2016. And while I acknowledged that Houser was the better side of the starting pitching matchup, I had reason to believe that it was skewing the line far too much.

When I looked at the Brewers trend of pulling their starting pitchers early in the game, they hadn’t had a starter go past the fifth inning in over a week, and have kept all of their starters on low pitch counts all season no long no matter how well they were pitching, I felt that even though I had to fade Houser, I wouldn’t have to fade him for all that long.

And when I looked at Colin Rea, he was certainly an unknown, but he had pitched well this year in limited action in relief, and the Brewers had been one of the worst hitting teams in the National League all season long. So, while Houser was better, and I didn’t have a clue what Rea was going to get me, I still felt that being able to get a Cubs team that had won 80% of their home games on the year, as home dogs, was too much value to pass up on.

At the end of the day, Houser and Rea were about a wash as both guys exited the game early and allowed three earned runs. The Cubs built an early 3-0 lead but couldn’t hold onto it, and this game needed extra innings to be decided. The Brewers scored two in the top of the tenth inning to take the lead, and while Chicago answered with a run in the bottom of the frame, they couldn’t tie it up, and for the second night in a row, the Brewers picked up a one-run road victory against the Cubs.

Anytime a game goes into extra innings, you want to be on the home team, and that is even more true this year, with the runner starting on second base rule. Having a home dog in extra innings is a high-value spot for sure, but the variance didn’t break our way, and we came up short. For today’s daily betting pick, we will stay right here in Chicago, as we break down the action between the Cubs and the Brewers.

Milwaukee Brewers (9-10) at Chicago Cubs (13-5)

The Milwaukee Brewers are in Chicago Sunday, looking for their third straight victory over the Cubs in game four of a four-game set. The Cubs took game one, and the Brewers have won back to back games the last two nights, to take the series lead. The modest two-game winning streak is tied for the longest winning streak of the year for Milwaukee.

For Chicago, the Cubs are left scratching their heads as they have now lost two straight games, both by one run, and both where they had a multiple run lead early in each game. This is the first time the Cubs have lost back to back games this year, and despite the two losses, they still have the best record in the majors, with a .722 winning percentage.

Starting today for the Cubs is Jon Lester (2-0 1.06 ERA), and for the Brewers, it is Josh Lindblom (1-0 5.68 ERA). The game total over/under is set at nine runs. The Cubs are -120 home field favorites. First pitch is scheduled for 11:20 AM PST from Wrigley Field in Chicago.


  • Milwaukee Brewers +1.5 (-195)
  • Chicago Cubs -1.5 (+160)
Money Line:

  • Milwaukee Brewers (+110)
  • Chicago Cubs (-120)
  • Total Runs:

    • Over 9 (-115)
    • Under 9 (-106)

    Milwaukee Brewers

    The Milwaukee Brewers were able to come from behind and eke out wins the last two nights, and it just might have saved their season. I know it might seem crazy to start thinking about the postseason, but we are nearing the halfway mark of the regular season, and September is just two weeks away. If Milwaukee had lost both of those games against the Cubs, they would have found themselves eight and a half games back of first place in the National League Central.

    That is the equivalent of twenty-two games back in a normal 162-game season. No team is ever coming back from twenty-two games in a normal season, and no team is coming back from eight and a half games this year. The Brewers still have a lot of work left to do, as they trail the Cubs by four and a half games, but without being even remotely dramatic, I can confidently say that these two wins have at least given the Brewers a puncher’s chance in the central, which they wouldn’t have had if they had lost.

    Josh Lindblom (1-0 5.68 ERA)

    Remember Josh Lindblom? He was a former second-round draft pick that came up with the Los Angeles Dodgers back in 2011 and looked like a kid with a lot of promise. After pitching well for the Dodgers out of the bullpen for a couple of years, he bounced around between the Phillies, Rangers, and Athletics, and by 2014, he was out of the Major Leagues.

    Lindblom took his talent to the KBO and had a lot of success pitching Korean baseball for the last several seasons. Last year, he won the KBP MVP Award when he went 20-3 with a 2.50 ERA. That performance got him his ticket back to the majors when he signed with the Milwaukee Brewers this offseason.

    Lindblom has made three starts for Milwaukee in 2020 and was quickly reminded that the MLB is not the KBO and has gotten roughed up. He is averaging just over four innings a start and has allowed eight earned runs in just 12.2 innings pitched. The strikeouts have been there as he has 20 K’s already this year, but he has also walked six guys and has allowed four home runs.

    Chicago Cubs

    The Cubs were walking on water until this two-game road bump. Chicago had won nine out of their previous ten games before dropping two straight against Milwaukee. I mentioned in my pick yesterday that Jason Kipnis has been a pleasant surprise for the Cubs this year, and he managed to get on base twice yesterday with a hit and a walk and scored a run.

    Only the Dodgers have more wins than the Cubs do right now, and LA has played four more games. I am certain Chicago didn’t love blowing leads on back to back days at home, but at the end of the day, teams are going to lose games, and I won’t let it change my opinion of this squad too much.

    Jon Lester (2-0 1.06 ERA)

    Jon Lester has been great this season. He has made three starts and has only allowed a total of two runs. He hasn’t even been letting runners get on base, as he has given up just seven hits in seventeen innings worked.

    The Cubs are 3-0 in games where Lester has started this year. Lester is just one year removed from being an All-Star and nearly winning the NL Cy Young Award in 2018, and he looks to be on pace to make another run at his first Cy Young Award this year.

    Who Do I Like?

    I don’t really understand the betting market on Jon Lester this year. In his last two starts, he opened as an underdog, and the sharps hammered it, and he closed out as a betting favorite. I have backed him in all three of his starts this season, and I am 3-0. In this game, he opened as a -150 home field favorite, and I felt like the Cubs were likely the play as home favorites.

    But in a strange reversal to earlier trends, the sharps have jumped on the other side, and this line has been dropping all morning. After opening up at -150, you can now back Chicago at just -120. Huh? What am I missing here?

    The Bet

    I am taking Chicago. The fact that they have blown leads in the past two games is a little concerning, but I still think they are the much better team in his game, and I know that Jon Lester is the much better starting pitcher. You’re telling me that I can get a recent All-Star, that is closing in on 200 career MLB wins, against a guy that was pitching in the KBO last year, and I barely have to lay any wood to do it?

    Ok, ill bite. Maybe the sharps are seeing something that I’m not, but right now, this seems like outrageous value. I expect Lester to continue mowing through hitters, and when Lindblom is forced to face guys like Kris Bryant, Anthony Rizzo, Kyle Schwarber, and Javvy Baez, he is going to wish he was back in Korea. Give me the Chicago Cubs today at home, laying -120!

    The Bet: Chicago Cubs -120

    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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