Cubs vs. Pirates Prediction, MLB Picks for Thursday, May 28

The first pitch of the Chicago Cubs (30-26) vs. the Pittsburgh Pirates (29-27) is set for 6:40 p.m. ET on Thursday, May 28, with the Pirates returning a 1.56x payout to win, via PrizePicks.

The Cubs can finally breathe, as they snapped their 11-game losing streak with a 10-4 win on Wednesday. They scored 4 runs in the first four innings, but the Pirates would climb back to tie the game. Chicago’s offense blew the game open with a 6-run seventh inning and never looked back. 

Now, the Cubs have the chance to salvage this four-game series with a series split if they win.

Below, we'll break down our Cubs vs. Pirates prediction and picks for Thursday’s MLB matchup, including the run line, over/under, and key player picks for PrizePicks.

Make your Cubs vs. Pirates picks on PrizePicks for tonight's game.

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Cubs vs. Pirates Prediction, Winner Payout, Over/Under – Thursday, May 28

For the series finale, the Cubs will send SP Colin Rea (4.09 xFIP across 11 appearances, 8 starts, and 54 IP in 2026) to the mound. Rea is having a consistency problem this season; his last start was the best of the year, going 7 innings and allowing 3 earned runs. Before that, he failed to get out of the sixth inning in five consecutive starts.

The last two weeks have been a disaster for Chicago. The Cubs have lost 15 of their 18 games and led the NL Central by 3.5 games on May 9 but are now 4.5 games behind the top spot. The pitching and hitting are struggling during this time, ranking last in wOBA (.258) and second-to-last in xERA (5.05). 

The Pirates counter with their star SP Paul Skenes (3.03 xFIP across 11 starts and 60 IP in 2026). Skenes has looked mortal at times this season. For the first time in his career, the reigning NL Cy Young winner is coming off back-to-back starts in which he allowed 4 or more earned runs. Skenes’ 3.00 ERA is exceptional for most pitchers, but when you enter the year with a career 1.96 ERA, it is a regression.

Even with Skenes not at his best, the Pirates have improved significantly from last season. Pittsburgh has not made the playoffs since 2015 and has finished in fourth place or worse in the NL Central since 2016. They are currently in last place in the NL Central but only 5.5 games behind first place.

Cubs vs. Pirates Winner Payout, Over/Under – Thursday, May 28

The Pirates enter Thursday’s game as home favorites, returning a 1.56x payout if they win outright, via PrizePicks Team Picks.

Here are the full payouts for the Cubs vs. Pirates game on PrizePicks.

• Spread: Pirates -1.5 (2.17x payout)
• Over/Under: 7.5 (1.88x payout on Over)
• Game Winner Payout: Cubs 2.32x | Pirates 1.56x

Make your Cubs vs. Pirates prediction on the spread or over/under on PrizePicks Team Picks to earn real money — available in 35 states!

Team Picks data is live at the time of writing and is subject to change.

Cubs vs. Pirates Prediction on Spread – 5/28/26

Here are the key game stats and trends behind our Cubs vs. Pirates prediction on the run line for Thursday, May 28.

Lock in your Cubs vs. Pirates prediction on PrizePicks before the first pitch.

Data used in this article is from Baseball Savant or FanGraphs.

• Skenes has an excellent history against the Cubs, with a career 2.94 ERA. Plus, Pittsburgh has a 4-3 record in his starts against Chicago.
• Of the nine Pirates players who have at least 1 at-bat against Rea, eight of them have recorded a hit, and seven have a lifetime .280 xBA or higher.
• Some of those successful players include OF Bryan Reynolds, who is 8 for 19 with 2 home runs, and 3B Nick Gonzalez, who is 5 for 12 with 1 home run.
• Cubs 3B Alex Bregman, second on the team with a .262 xBA, is a career 1 for 6 with a .101 xBA against Skenes. Left fielder Ian Happ, who leads the team with a .440 xSLG, is a career 3 for 12 with a .336 xSLG.
• Skenes’ 4.6% barrel rate allowed ranks in the 84th percentile; that could be challenging for the Cubs, who rank 27th in the league with a 5.6% barrel rate since May 9.

Cubs vs. Pirates Picks, Player Stats for PrizePicks – 5/28/26

Here are the top Cubs vs. Pirates picks to target on PrizePicks for Thursday, May 28. Today’s MLB picks for PrizePicks include Oneil Cruz and Nico Hoerner.

Cubs 2B Nico Hoerner vs. Pirates: 5 Hitter Fantasy Score

• Hoerner is one of the few Cubs hitters who has success against Skenes, going 4 for 12 with 1 home run.
• His 11.4% whiff rate ranks in the 97th percentile, while Skenes is only inducing a 24.7% whiff rate that sits in the 47th percentile.
• Do not expect Hoerner to leave an at-bat empty-handed, as his 7.7% strikeout rate is the lowest in the league, and he has never struck out against Skenes.
• Even if Skenes gets Hoerner to chase outside the strike zone, the Cubs’ second baseman can still be impactful, as his 74.1% chase contact rate is well above the league average of 58.0%. Skenes does not do well at getting opponents to swing and miss, as his 64.7% chase contact rate is higher than league average.

Add Nico Hoerner to your PrizePicks Lineup now.

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Pirates OF Oneil Cruz vs. Cubs: 1.5 Hits + Runs + RBI

• Cruz has a solid history against Rea, going 2 for 8 with a double.
• The Pirates center fielder has one of the most explosive bats in the game, including a league-leading 61.4% hard-hit rate. That should fare well against Rea, who’s allowing a 45.6% hard-hit rate (12th percentile).
• Cruz has been on fire in this series, going 5 for 11 with 1 run and 1 RBI.
• Rea is allowing a 91.7 mph average exit velocity, which ranks in the fourth percentile. That could be a huge problem against Oneil, whose 96.1 mph average exit velocity is the best in baseball.

Add Oneil Cruz to your PrizePicks Lineup now.

Make Cubs vs. Pirates Picks on PrizePicks

The Cubs returned to the win column after losing 11 straight games. They will try to manage a split in this four-game series but will have to go through reigning NL Cy Young winner Paul Skenes.

Don’t wait until the first pitch happens — make your Cubs vs. Pirates picks on PrizePicks now and earn real money if you’re right.

Pick players, predict More or Less on their stats, and cash in if you’re right. With Team Picks, you can make predictions on game winners, spreads, and over/unders, now available in 35 states.

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