Walk-Off Wagers: MLB Best Bets Today (Predictions for Red Sox-Brewers, Cardinals-Orioles, Giants-Tigers)

Breaking down the best bets for the MLB action on Monday,May 26, including a pick for the Boston Red Sox-Milwaukee Brewers clash.

The Red Sox are favored with Garrett Crochet on the mound. / Eric Canha-Imagn Images

Happy Memorial Day, MLB fans! 

As we all enjoy the last bit of the holiday weekend, Major League Baseball has a terrific slate lined up on Monday with seven games that will have their first pitch before 5 p.m. EST. 

I’m eyeing three of those early games on Monday for today’s best bets, as there are some pitching matchups that I believe are worth taking advantage of this afternoon.

One of those matchups features Boston Red Sox ace Garrett Crochet taking on the Milwaukee Brewers in Milwaukee. Crochet has been one of the best pitchers in baseball this season, and he should give the Sox a huge advantage early in this game.

Let’s dive into each of the best bets for Monday’s action.

 MLB Best Bets for Monday, May 26

Odds via DraftKings Sportsbook.

• Boston Red Sox First 5 Innings Moneyline (-160) vs. Milwaukee Brewers
• San Francisco Giants First 5 Innings Moneyline (-120) vs. Detroit Tigers
• St. Louis Cardinals Moneyline (-110) vs. Baltimore Orioles

Boston Red Sox First 5 Innings Moneyline (-160) vs. Milwaukee Brewers

Crochet enters Monday’s start with 1.98 ERA through 11 starts this season, and his underlying metrics back that up. Crochet ranks in the 99th percentile in pitching run value, 73rd percentile in expected ERA and 84th percentile in strikeout percentage.

Now, Crochet gets a shot at a Milwaukee team that is just 25th in MLB in OPS in the 2025 season. 

The Brewers will counter with Chad Patrick on the mound as an extended opener. Patrick has made 10 starts this season after beginning as a bullpen arm, but he’s only pitched through five innings on five occasions. 

He does have a solid 3.23 ERA this season, but the Brewers are just 4-7 in his outings.

Now, Boston is just 6-5 when Crochet is on the mound, but I’m going to leave both bullpens out of this game and simply take the Sox in the first five innings.

Crochet has given up two or fewer earned runs in 10 of his 11 starts, and the Sox have come alive at the plate as of late, ranking seventh in runs scored and sixth in OPS over the last 15 days.

As long as Boston gets its ace a little run support, Crochet should take care of the rest on Monday. 

San Francisco Giants First 5 Innings Moneyline (-120) vs. Detroit Tigers

The San Francisco Giants are relying on an opener on Memorial Day, as righty Hayden Birdsong will make his second start of the 2025 season after tossing five innings of one-run ball (unearned) in his first start of 2025. 

Birdsong has a 1.91 ERA this season, but his expected ERA is a little higher – all the way up at 3.74.

Still, I think he gives the Giants the advantage against Detroit and righty Keider Montero (5.28 ERA) on Monday. Montero has given up 35 hits in 30.2 innings of work, and he’s given up three or more runs in four of his six outings in 2025.

He ranks in the ninth percentile in pitching run value and 24th percentile in expected ERA, per Statcast. 

Even if Birdsong isn’t able to get through five innings, the Giants have the best bullpen ERA (2.62) in Major League Baseball this season. So, I trust San Francisco to keep the Tigers in check early on.

Montero has not pitched well enough this season to back the Tigers to hold up in the early innings on Monday. 

St. Louis Cardinals Moneyline (-110) vs. Baltimore Orioles

The last afternoon matchup that I’m eyeing on Monday features a red-hot St. Louis Cardinals team that has won seven of its last 10 games to move into the No. 2 spot in the NL Central standings. 

St. Louis has struggled a bit on the road (11-15 straight up in 2025), but the Cardinals have a great matchup against a Baltimore Orioles team that is 8-15 at home and 18-34 overall – sitting in last place in the AL East. 

Baltimore is also sending a struggling starter to the mound in veteran right-hander Charlie Morton. This season, Morton has a 7.68 ERA, and he was pulled from the rotation last month after a brutal start to the campaign.

As a starter, Morton has a 10.22 ERA in six outings, and the O’s are 0-6 in those games. Overall, Baltimore is 0-12 when Morton takes the mound in the 2025 season. Not great. 

He’ll take on Erick Fedde (3.77 ERA), who has not fared too well for the Cardinals, leading St. Louis to just three wins in 10 appearances. However, Fedde is a much better pitcher than Morton this season, and the Cardinals outrank the Orioles in bullpen ERA.

Baltimore has the fourth-worst bullpen ERA (5.46) in MLB this season, so even if Morton is pulled early, it’s hard to trust the arms behind him to keep things in check. 

The Cardinals have been extremely hot to close the month of May, and I expect that to continue this afternoon.

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Odds refresh periodically and are subject to change.

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