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Expert Picks & Predictions for Cubs vs Pirates on May 26

Chris Amberley

By Chris Amberley in MLB Baseball

Published:


Konnor Griffin swipes a tag on Alex Bregman during a Cubs vs Pirates game.
May 25, 2026; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates shortstop Konnor Griffin (6) tags out Chicago Cubs third baseman Alex Bregman (3) at second base on a steal attempt during the fifth inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images
  • The Pirates are -134 moneyline favorites over the Cubs tonight
  • Pittsburgh starter Braxton Ashcraft brings a 2.89 ERA and tidy 1.03 WHIP into play
  • Don’t miss the top expert picks and predictions for Cubs vs Pirates on May 26, below

The Pittsburgh Pirates (28-26) continue their series against the visiting Chicago Cubs (29-25) tonight, with first pitch scheduled for 6:40 PM ET at PNC Park. The Pirates enter this matchup as the home favorite in the MLB odds, after edging out the Cubs in a 2-1 victory yesterday. That win was powered by a clean defensive performance and a home run from Henry Davis.

The road underdog Cubs will look to bounce back after two errors overshadowed Michael Busch’s solo shot in the series opener. The MLB weather forecast is calling for a perfect night for baseball, with clear skies and 77 degree temperatures on deck.

Below, you’ll find my top expert picks and predictions for the Cubs vs Pirates matchup on May 26th.

Expert Picks for Cubs vs Pirates on May 26

  • Pirates Moneyline (-134 at Caesars)
  • Under 8.5 Runs (-124 at Caesars)
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My favorite picks tonight are the Pirates moneyline and under 8.5 runs. Finding the right angles requires examining the statistical differences in the MLB starting lineups. The Pirates hold a clear pitching advantage with probable starter Braxton Ashcraft taking the mound against a Cubs team who’ll be throwing a bullpen game. Ashcraft boasts a 2.89 ERA and a 1.03 WHIP over 62.1 innings this campaign, and has flummoxed opposing hitters all season. His 3.16 FIP indicates his production is sustainable. Over his last 10 appearances, the right-hander has maintained a .215 opponent batting average while averaging 6.23 innings per start.

The Cubs’ pitching staff sports a 4.09 team ERA compared to the Pirates’ 3.79 mark. Given Ashcraft’s consistency and the Pirates’ slight offensive edge in team batting average (.274 at home against the Cubs’ .230 on the road), backing the home team to win outright is a must.

Both offenses show vulnerabilities that lean favorably toward a lower-scoring affair. The Cubs average 8.15 strikeouts per nine innings, while the Pirates strike out 8.80 times per contest. Furthermore, both pitching staffs have effectively limited baserunners.

The Pirates hold opponents to a .225 batting average, and Cubs pitchers limit hitters to a .236 mark. I expect the arms to limit offensive production tonight, keeping the final score below the total.

Odds for Cubs vs Pirates on May 26

Odds as of May 26. Claim the BetMGM promo code to bet on the Cubs vs Pirates today.

If you want to tail my picks tonight, you’ll need access to multiple betting sites. For the moneyline and total wagers, make sure you visit Caesars. They’re offering the best price on the Pittsburgh moneyline at -134, while they’re also one of the only books who are posting an 8.5 total.

As for the MLB props bets which you’ll see below, DraftKings has the best odds on my two favorite wagers by a wide margin.

Predictions for Cubs vs Pirates on May 26

  • Braxton Ashcraft Over 5.5 Strikeouts (-111 at DraftKings)
  • Bryan Reynolds Over 0.5 Hits (-238 at DraftKings)
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For the player prop market, I am targeting the strikeout totals. Ashcraft’s impressive 9.39 K/9 rate translates perfectly to this matchup. Taking the mound against a lineup that regularly struggles with punchouts, the right-hander has a fantastic opportunity to clear this modest number. Per the MLB batter vs pitcher stats, he owns a 32% K rate over 49 at-bats against hitters in the Chicago lineup.

For an additional offensive prop, I look to Bryan Reynolds. He remains a consistent catalyst for the Pirates with a .251 average, 32 RBIs, and 31 runs scored, making him a reliable option to reach base safely at least once.

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Chris Amberley
Chris Amberley

Sports Writer

As SBD's resident Swiss Army Knife, Chris covers virtually every sport including NFL, PGA, NBA, MLB, NCAAB, NCAAF and the Olympics. A true grinder, he'd rather pick off small edges in the player props market than swing for the fences with a 5-leg parlay.

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