Boston Red Sox vs Milwaukee Brewers MLB Pick May 27th

by | May 27, 2025 | mlb

Rafael Devers Red Sox

The Boston Red Sox (27-29) head to Milwaukee to face the Brewers (32-26) in what should be an intriguing pitching matchup between two starters looking to find their footing this season. Both teams have struggled offensively in recent games, making this an important series opener as each club tries to gain momentum heading into the summer months.

Quick Picks:

  • Best Bet: Brewers Moneyline (-115) ★★★☆
  • Top Prop: Jackson Chourio Over 1.5 Total Bases (+120) ★★★☆
  • Value Play: Over 8.5 Runs (+100) ★★★☆

Boston Red Sox vs Milwaukee Brewers Betting Odds & Latest Line Movement

Market Boston Red Sox Milwaukee Brewers
Moneyline +105 -115
Run Line +1.5 (-160) -1.5 (+140)
Total Over 8.5 (+100) Under 8.5 (-120)

Opening Line: Brewers -120, Total 8

Sharp Money Analysis: Where Pro Bettors Are Placing Their Wagers

Early sharp money has pushed the total up from 8 to 8.5, indicating professional bettors see value in the over despite both teams’ recent offensive struggles. The Brewers moneyline has seen slight buyback, moving from -120 to -115, suggesting some value on the home team at the current number. The run line markets have remained relatively stable, with most of the action concentrating on the moneyline and total markets for this matchup.

Pitching Matchup: Cooper Criswell vs Aaron Civale – Who Has the Edge?

Boston Red Sox: Cooper Criswell (0-0, 10.38 ERA)

  • 10.38 ERA across 4.1 innings pitched
  • Only 1 strikeout with a concerning 2.54 WHIP
  • Limited major league experience makes him difficult to project
  • Has struggled with command in his limited appearances

Milwaukee Brewers: Aaron Civale (0-1, 9.00 ERA)

  • 9.00 ERA over 7 innings pitched this season
  • 5 strikeouts, 3 walks, and a 1.57 WHIP
  • Has historically shown better control than his early 2025 numbers suggest
  • Looking to rebound against a struggling Red Sox offense

Advantage: Milwaukee Brewers (slight) – Civale has a longer track record of MLB success and is more likely to bounce back from early struggles

Bullpen Breakdown

The Brewers hold a clear advantage in the bullpen department, with their relief corps ranking among the more reliable units in the National League. Milwaukee’s bullpen has posted a 3.65 ERA this season compared to Boston’s 4.28 mark. The Red Sox bullpen has shown signs of fatigue in recent games, having been forced to cover additional innings due to short starts. If this game comes down to middle relief as expected with both starters struggling, Milwaukee’s fresher and more consistent bullpen should give them an edge in the later innings.

Key Betting Trends & Team Statistics That Matter

  • Boston is 3-7 in their last 10 games and has scored just 4 runs total in their last three contests
  • The Red Sox are 12-16 on the road this season
  • Milwaukee is 19-10 at American Family Field in 2025
  • The Brewers are 7-3 in their last 10 home games
  • Boston is 8-14 as an underdog this season
  • The OVER is 6-2 in games featuring starting pitchers with ERAs above 8.00 this season

Jackson Chourio’s Emergence: Young Star Providing Spark for Brewers

Jackson Chourio has been a revelation for the Brewers in recent weeks, including a leadoff home run in Monday’s game. The young outfielder’s development has been crucial for a Milwaukee offense that has otherwise been inconsistent. Chourio is batting .286 with 5 home runs and 7 stolen bases over his last 15 games, providing much-needed production at the top of the order. His matchup against the struggling Criswell presents a prime opportunity for Chourio to continue his hot streak and potentially influence the outcome of this game significantly.

American Family Field Factor: How the Venue Influences Today’s Game

American Family Field continues to play as a hitter-friendly environment, particularly for power hitters, with its retractable roof ensuring consistent playing conditions. The park has a 1.12 home run factor this season, making it the 8th most homer-friendly venue in MLB. This setting could compound problems for both struggling starters, especially given Criswell’s tendency to allow hard contact. The Brewers have leveraged their home-field advantage effectively this season, going 19-10 at American Family Field. Weather will be a non-factor with the roof likely closed for this evening contest, creating ideal hitting conditions that favor the over.

Expert Prediction & Best Bets for Boston Red Sox-Milwaukee Brewers Showdown

Primary Play: Brewers Moneyline (-115)

The Brewers present solid value on the moneyline given their significant home-field advantage (19-10 at American Family Field) and Boston’s ongoing offensive struggles. While neither starting pitcher inspires confidence, Civale has a longer track record of MLB success and is more likely to give Milwaukee 4-5 serviceable innings. The Brewers’ superior bullpen should also prove decisive in what projects to be a game heavily influenced by relief pitching. Boston’s 3-7 record in their last 10 games further supports backing the home favorite.

Strong Value Play: Over 8.5 Runs (+100)

Despite both teams’ recent offensive struggles, this total presents value at even money. American Family Field’s hitter-friendly dimensions combined with two struggling starters (Criswell: 10.38 ERA, Civale: 9.00 ERA) creates a recipe for runs. The sharp money movement from 8 to 8.5 indicates professional agreement with this assessment. Historical data shows the OVER hitting at a 75% rate in games featuring dual starters with ERAs above 8.00, making this even money proposition highly attractive.

Worth Considering: Red Sox/Brewers Over 4.5 Runs First 5 Innings (-110)

If you’re hesitant about the full game total but still want to capitalize on the pitching mismatch, the first five innings over presents an intriguing alternative. Both Criswell and Civale have struggled with early inning performance, and neither is likely to work deep into the game. This bet allows you to target the weakest part of both teams (starting pitching) while avoiding the more unpredictable bullpen innings. The -110 price offers reasonable value given the pitching matchup.

Player Props Worth Targeting in Today’s Matchup

Player Prop Odds Rating
Jackson Chourio Over 1.5 Total Bases +120 ★★★★☆
Jarren Duran To Record a Hit & Run +165 ★★★☆☆
Aaron Civale Under 4.5 Strikeouts -135 ★★★☆☆
Cooper Criswell Under 13.5 Outs Recorded -120 ★★★★☆

Final Thoughts: Bullpen Battle Likely to Determine Winner

This matchup features two struggling starters who are unlikely to work deep into the game, setting up a battle of bullpens that should favor Milwaukee. The Brewers’ superior home record and Boston’s offensive slump create a favorable situation for the home team, though the high combined ERAs of the starting pitchers suggest runs could come in bunches early. The line movement toward the over appears justified given the pitching matchup. For bettors looking for the most reliable play, the Brewers moneyline offers the best combination of value and probability in what could otherwise be a volatile game environment.

Score Prediction: Brewers 6, Red Sox 4

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