Free Picks: Milwaukee Brewers vs Chicago Cubs

Jordan Horrobin
Jordan Horrobin
MLB Free Picks – Best Bets of the Week
Cubs vs Brewers Week 14
Milwaukee Brewers vs Chicago Cubs, MLB, American Family Field

The Milwaukee Brewers (47-33) will play host to the Chicago Cubs (42-38) for the afternoon finale of their three-game series on Wednesday, and it’s the Cubs’ last chance until August to double dip against the National League Central-leading Brewers. Milwaukee owns a five-game lead on Chicago, entering Tuesday, which is coincidentally the same gap in their season series (the Brewers lead the Cubs, 8-3). The Cubs are 16-25 on the road this season, and that includes a 1-4 mark at Milwaukee’s American Family Field.

Cubs have a chance to capitalize against Brewers’ newcomer

The Brewers will send Aaron Ashby to the mound for his MLB debut on Wednesday, and that could be just what the Cubs need to pull off an upset.

Chicago enters as the hefty +185 money line underdog (10Bet), which is the second-longest among the day’s MLB picks. Milwaukee is a -233 money line favorite, and we’re not so sure those odds are justified.

Yes, the Brewers snuck by the Cubs with a 2-1 win on Tuesday, further padding their NL Central lead and extending their season series lead over the Cubs to an 8-3 margin. But now they’re looking to deploy a bullpen game in Wednesday’s series finale, with a fairly average minor leaguer coming up to get the game started.

Ashby is 4-1 but with a 4.50 ERA in 12 appearances (six starts) for the Brewers’ Triple-A affiliate this season. The 2018 fourth-rounder has been better at lower levels, en route to a 3.69 ERA in his minor league career, but the Triple-A ERA doesn’t jump off the page. What does jump off the page, to be fair, is his 13.3 strikeouts-per-nine rate this year (56 strikeouts in 38 innings). It’s fair to say his stuff plays, but his accuracy might not always be there (evidenced by his 5.7 walks-per-nine rate).

After Ashby, who’s only expected to toss two or three innings, the Brewers will turn the game over to their bullpen. And for as great as Milwaukee’s starting corps has been, with a 3.31 ERA (seventh in MLB), the relievers have been less impressive (4.01 ERA, 14th in MLB). That makes this a good time to strike with the underdog.

We know the Cubs are in a bind right now, having lost five in a row and eight of 11. But picking on a rookie making his debut sounds like the perfect way to snap out of a rough stretch.

Jake Arrieta will be on the mound for Chicago, and he’s lost both starts against Milwaukee this year. But he also gave his team a fighting chance in both games: last time out against Milwaukee, he allowed one run over six innings while striking out eight. The time before that, he allowed three runs over five innings while striking out five. 

Another competitive outing from Arrieta, paired with some offense against Ashby and the Brewers’ mediocre bullpen, makes the Cubs a compelling underdog option for our BetPicks prediction.

Join 10Bet Now


  • Chicago is 3-7 on the money line in its past 10
  • The UNDER has cashed in seven of the Cubs’ past 10 games
  • Milwaukee is 9-1 on the money line in its past 10
  • The UNDER has cashed in five of the Brewers’ past eight games

Jordan Horrobin is a freelance sports journalist based in Toronto, Ontario, who enjoys sports-related research and telling engaging stories. His work can also be found at Sportsnet, Forbes and elsewhere. Though he abandoned most of his team-specific fandoms in the interest of unbiased analysis, Jordan roots hard for his fantasy football/hockey teams (and he's a complete homer for all things Ohio University).