Cubs vs Pirates Same Game Parlay May 28: Three Legs Built Around Paul Skenes

The Pittsburgh Pirates host the Chicago Cubs on Thursday, and this matchup gives us one of the most compelling same game parlay (SGP) opportunities on the board for May 28. At the center of it all is Paul Skenes, one of the best young starters in baseball, whose strikeout stuff and ability to limit runs makes multiple legs of this parlay work together naturally.

If you are new to same game parlays, here is the quick version: an SGP is a single parlay where all the legs come from the same game. Sportsbooks like DraftKings and FanDuel offer these on most major contests. The odds multiply across the legs, which means a modest investment can return a meaningful payout — but the legs have to be carefully chosen so they are not working against each other. The three legs below were built to complement one another. You can check FanDuel promo codes before placing your first SGP.

Leg 1: Paul Skenes OVER Strikeouts

Paul Skenes is averaging 9.75 strikeouts per nine innings in 2026, with 65 punchouts across 60.0 innings through 11 starts. His combination of a high-velocity fastball and a splinker that generates swings below the zone makes him one of the hardest pitchers to make contact against in all of baseball. Against the Cubs on Thursday, he faces a lineup that has shown elevated strikeout tendencies this season.

The over on Skenes’s strikeout prop is the anchor of this SGP because it is the most reliable performance indicator in the build. When a pitcher at his level faces a lineup with swing-and-miss tendencies, the strikeout total is often the most predictable individual stat of the game. He has gone deep into games consistently this season, posting a WHIP of just 0.82, which means he is not burning through his pitch count on walks. More pitches toward the strike zone means more chances for strikeouts, which supports the over.

Leg 2: Pirates Team Total OVER

Colin Rea takes the mound for Pittsburgh in this game, and the Pirates offense has been productive at home in 2026. The Cubs are throwing their own starter against a Pittsburgh lineup that has shown the ability to generate traffic against mid-tier pitching. A Pirates team total over plays well in an SGP anchored by Skenes because it creates a situation where Pittsburgh wins (or at least scores) without needing to blow the game open — keeping Skenes in the game longer and providing more innings for his strikeout total to climb.

When you have an elite pitcher like Skenes on your team, the odds of the team scoring enough runs to stay competitive are elevated. A solid bullpen game and a pitcher keeping the opposing team off the board makes the team total over a natural complement to the strikeout leg. It is the kind of correlation that SGPs are designed to reward. Learn more about DraftKings promo codes if this is your first time building a same game parlay there.

Leg 3: Paul Skenes UNDER Earned Runs

A third leg that rounds out this parlay is the under on Skenes’s earned runs allowed. His 0.82 WHIP and 3.00 ERA through 11 starts tell the story of a pitcher who minimizes hard contact and limits the damage when opponents do get on base. Against the Cubs, who have struggled to produce consistent run support against elite starters, the under on his earned runs is a clean, low-correlation add to the strikeout over.

The key mechanic here is that a low-ERA pitcher who generates lots of strikeouts creates a reinforcing loop: more strikeouts means fewer baserunners, and fewer baserunners means fewer opportunities for earned runs. The two legs are naturally correlated in a positive direction, which is exactly what you want when building an SGP. Pairing both Skenes legs with the Pirates team total creates a parlay where each outcome supports the others rather than working against them.

The Full Parlay

Here is how the three legs come together for the Cubs vs Pirates SGP on May 28. Individual odds were not available at time of publication — check your preferred sportsbook for current pricing before placing this bet.

• Paul Skenes OVER strikeouts vs Chicago Cubs
• Pittsburgh Pirates team total OVER
• Paul Skenes UNDER earned runs allowed

This three-leg SGP gives you a clean narrative backed by real 2026 performance data. Always shop lines across multiple books before placing any parlay — line differences compound across legs and can meaningfully impact your total payout.