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Cubs vs. Pirates Prediction, Odds, Probable Pitchers, Prop Bets for Wednesday, May 27

Can the Pirates take Game 3 of this series?
The Pittsburgh Pirates and second baseman Brandon Lowe are favored on May 27.
The Pittsburgh Pirates and second baseman Brandon Lowe are favored on May 27. | Charles LeClaire-Imagn Images

The Chicago Cubs have gone in the tank over the last two weeks, losing 10 games in a row to fall to last place in the NL Central.

Now, the Cubs are only 4.5 games out of the top spot, but they’re in arguably the toughest division in baseball right now, so climbing out of the basement won’t be easy.

The Cubbies will look to turn things around in the third game of their four-game set with the Pittsburgh Pirates on Wednesday night after scoring just two runs total in the first two games of this matchup. 

The Pirates won 12-1 on Tuesday night, and they’re set as small favorites at home with Bubba Chandler (4.79 ERA) on the mound against Chicago’s Jameson Taillon (5.20 ERA). 

Can the Cubbies turn things around against the 23-year-old Chandler? Chicago already has a 7-6 win over the Pirates (back in April) with Chandler on the bump. 

Let’s dive into the odds, a player prop to bet and my prediction for this NL Central showdown. 

Cubs vs. Pirates Odds, Run Line and Total

Odds via DraftKings Sportsbook

Run Line

  • Cubs -1.5 (+141)
  • Pirates +1.5 (-171)

Moneyline

  • Cubs: -108
  • Pirates: -112

Total

  • 9 (Over +101/Under -122)

Cubs vs. Pirates Probable Pitchers

  • Chicago: Jameson Taillon (2-4, 5.20 ERA)
  • Pittsburgh: Bubba Chandler (1-6, 4.79 ERA)

Cubs vs. Pirates How to Watch

  • Date: Wednesday, May 27
  • Time: 6:40 p.m. EST
  • Venue: PNC Park
  • How to Watch (TV): Marquee Sports Network, MLB.TV
  • Cubs record: 29-26
  • Pirates record: 29-26

Cubs vs. Pirates Best MLB Prop Bets

Pirates Best MLB Prop Bet

  • Brandon Lowe to Hit a Home Run (+355)

Earlier today, I shared in SI Betting’s best home run props column – Daily Dinger – why Lowe is a great target against Taillon: 

Pittsburgh Pirates second baseman Brandon Lowe is red hot right now, hitting .385 with one homer and a 1.005 OPS, and he’s hitting .300 with six homers over the last four weeks. 

Overall, Lowe is up to 13 home runs, and 10 of his homers have come against right-handed pitching. 

So, he’s a great target against the Cubs and the right-hander Taillon, who has given up 17 home runs in 10 starts while posting a 5.20 ERA. Taillon has struggled against Lowe in his career, giving up four hits, one double and two home runs in 14 at-bats with the Pirates slugger posting a 1.197 OPS. 

Lowe is priced at +355 – which isn’t a massive value – but I’m buying the Pirates star to take advantage of this favorable matchup on Wednesday. 

Cubs vs. Pirates Prediction and Pick

The Cubs’ offense has fallen off a cliff over the last 15 days, ranking 28th in runs scored and 29th in OPS, making them a hard team to bet on – even against Chandler.

The 23-year-old has given up three or more runs in six of his 10 starts this season, and he ranks in the 33rd percentile in expected ERA. The Pirates, as a result, are just 2-8 in his 10 outings.

Still, I can’t trust the Cubbies with Taillon on the mound. The veteran has a 5.20 actual and expected ERA, ranking in the 16th percentile in expected ERA and the 36th percentile in expected BAA. 

Pittsburgh is a top-six team in OPS and runs scored this season, and it should tee off on Taillon, who has allowed a ton of homers already this season. 

I’ll take this short moneyline price for the Pirates at home with the Cubs in the worst slump in MLB. 

Pick: Pirates Moneyline (-112 at DraftKings)


Odds refresh periodically and are subject to change.

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Published | Modified
Peter Dewey
PETER DEWEY

Peter is a senior editor for Sports Illustrated Betting. He has worked as a writer and editor for BetSided, NBC Sports, the Connecticut Sun and the Meriden Record-Journal covering the NBA, WNBA, NFL, MLB, and more. A New York City resident, he is a hoops fanatic with a soft spot for his New York Knicks.

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