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Best MLB Parlay Picks Today: Elite Pitchers Highlight the Monday Slate

Published: May 26, 2025, 08:47 AM ET
4 min read
Best MLB Parlay Picks 2025 05 26

Monday is a day of pitching aces in Major League Baseball. I’m backing three teams with strong pitchers on the mound for my parlay. 

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Let’s get into our three-leg parlay, featuring the Red Sox, Yankees, and Phillies at +318.

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Red Sox vs. Brewers (2:10 PM, EST)

Red Sox Moneyline (-156) at FanDuel Sportsbook

The Boston Red Sox will face the Milwaukee Brewers in the second game on the Monday slate. Both teams are right below .500, so this series will be critical for each club to continue staying alive in the playoff race. 

Boston hasn’t played like a championship contender, but they’re the more talented team. This is especially true with Garrett Crochet on the mound. 

Crochet has been tremendous this season. He is 4-3 with a 1.98 ERA and a 1.07 WHIP, while allowing just 51 hits over 68.1 innings.

The Red Sox are one game below .500, so Crochet is their ticket to getting even on the season. Boston’s offense has been very inconsistent, but they shouldn’t need many runs to win with their ace on the hill.

The Red Sox offense has scored 35 more runs than the Brewers, and they have hit 24 more home runs. 

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Blue Jays vs. Rangers (4:05 PM, EST)

Rangers Moneyline (-152) at FanDuel Sportsbook

The Texas Rangers have one of the best pitchers in baseball on the mound in Jacob deGrom. deGrom has been able to stay healthy, and it has worked wonders for his season stats. 

The pitcher is 4-1 with a 2.33 ERA and a 0.93 WHIP. There was a time when deGrom was the best pitcher in baseball, and even at 36, he has shown a career resurgence. 

The Rangers are coming off a win over the White Sox, so they have momentum. However, their Monday opponent, the Toronto Blue Jays, will be a slightly tougher task. 

Kevin Gausman will throw for the Blue Jays, and he has been solid in 2025. Gausman is 4-4 with a 4.03 ERA and a 0.98 WHIP. 

Gausman has similar numbers to deGrom, but the Rangers win at home, and the Blue Jays tend to give up games as visitors.

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Dodgers vs. Guardians (6:10 PM, EST)

Dodgers Moneyline (-186) at FanDuel Sportsbook

Every team runs into tough times over the course of 162 games, and the Dodgers are in this period of their schedule currently. They have won just three of their past nine games. 

Los Angeles’ talent is outstanding, so despite the losing streak, they’re still 32-21 and in first place in the National League West. 

They have a great chance to rebound with Yoshinobu Yamamoto on the mound on Monday. Yamamoto is 5-3 with a 1.86 ERA and a 0.91 WHIP. 

In 58 innings, he has allowed just 35 hits with 68 strikeouts. Yamamoto is in line to win the Cy Young award, and should give the Guardians trouble on Monday. 

Cleveland has been excellent at home with a 14-8 record. However, Los Angeles’ talent should overwhelm the Guardians in this matchup.

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Tanner Kern

Tanner Kern

Sports Betting Analyst & On-Air Host

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Tanner Kern has been working in the betting industry since 2020. He currently is a social media content creator at DraftKings and contributes to multiple sites in addition to WSN, including Forbes and VSiN. He is also the cohost of the podcast Ride the Line at WSN.
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