Best MLB Bets Today: Can the Pirates Finally Get Paul Skenes a Win?

Pirates ace Paul Skenes is already a superstar in his second season, but Pittsburgh has lost all four starts in May. He’ll face a struggling Milwaukee lineup tonight, but can he get the support needed to break the streak and get a win? Below, we’ll share our favorite bet for his game today and two others we love.

The odds we use are taken from Caesars Sportsbook. If you’d like to try Caesars, use promo code WSNDYW to claim a “Bet $1, Get Ten 100% Profit Boost Tokens” offer.

Milwaukee Brewers vs. Pittsburgh Pirates (6:40 PM EST)

PICK: Brewers ML (+105) at Caesars Sportsbook

The Brewers will have their ace on the mound tonight in Freddy Peralta (5-3, 2.59 ERA, 1.06). The 28-year-old struggled in the role last season, but has been fantastic in 2025. While he isn’t going deep into games, we expect him to go at least six against one of the worst lineups in baseball.

The Pirates have been unable to produce at the plate this season. They own the worst OPS in baseball (.617), which says a lot when you consider how bad the White Sox and Rockies have been. While Milwaukee ranks twenty-seventh in OPS (.657), there is a 40-point gap between the two.

The Pirates will have one of the league’s top pitchers starting in Paul Skenes (3-5, 2.44 ERA, 0.94 WHIP). The 22-year-old is coming off stellar performances against the Phillies and Mets, but the Pirates have lost their last four starts. Between a bad lineup and an unreliable bullpen, Skenes doesn’t have the support to lead Pittsburgh to wins.

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Baltimore Orioles vs. Boston Red Sox (1:35 PM EST)

PICK: Red Sox ML (-130) at Caesars Sportsbook

Red Sox starter Brayan Bello (2-1, 4.02 ERA, 1.69 WHIP) will be looking to bounce back tonight. He was hammered hard his last time out, but he’s been a reliable arm for Boston this season. We like he chances to turn things around this afternoon against an Orioles team that owns a lowly .216 against him over 74 at-bats.

Baltimore starter Cade Povich (1-3, 5.23 ERA, 1.45 WHIP) hasn’t shown much growth in his second MLB season. His subpar season started with a game against the Red Sox in which he allowed three runs on five hits and two walks over 4 ⅓ innings. While Boston’s lineup has been mediocre in 2025, they have plenty of talent to torch this struggling young pitcher.

Both of these bullpens have been shaky this season, but Boston’s has been far better lately. That will make all the difference today and help the Red Sox seal a key win. 

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Texas Rangers vs. Chicago White Sox (7:40 PM EST)

PICK: Under 8 (-105) at Caesars Sportsbook

The Texas Rangers will have one of the league’s hottest pitchers on the mound in Tyler Mahle (5-1, 1.47 ERA, 0.98 WHIP). The righty is enjoying the best campaign of his career and hasn’t shown any signs of slowing down. Look for him to deliver another gem tonight against a terrible Chicago lineup that owns a .077 average against him.

The White Sox have seen starter Sean Burke (2-5, 4.69 ERA, 1.52 WHIP) develop over the last month. While an excellent Cubs lineup hammered him in his last start, he allowed just two runs over his previous two outings.

We would like Burke to return to form against a Rangers team that has been struggling at the plate. They own the fifth-worst OPS (.657) in the league, and remain without their top hitter with Corey Seager on the mound. That’s why we are trusting the 25-year-old and a bad White Sox bullpen to keep the damage to a minimum tonight.

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