MLB Best Bets Monday: 3 Picks & Predictions (5/27)

MLB Best Bets Monday: 3 Picks & Predictions (5/27) article feature image
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(Photos: Getty Images) Pictured: Cooper Criswell (left) and Robert Gasser (right).

With an 11-game Memorial Day MLB slate for Monday, May 27, our staff has locked in on three MLB best bets, including picks and predictions for Red Sox vs Orioles and Cubs vs Brewers.

Continue reading below for our Monday MLB Best Bets.


MLB Best Bets Monday: 3 Picks & Predictions (5/27)

The team logos in the table below represent each of the matchups that our MLB betting staff is targeting from today's slate of games. Click on the team logos for any of the matchups below to navigate to a specific MLB bet discussed in this article.

GameTime (ET)Pick
4:10 p.m.
1:35 p.m.
1:35 p.m.
Specific betting recommendations come from the sportsbook offering preferred odds as of writing. Always shop for the best price using our MLB Odds page, which automatically surfaces the best lines for every game.

Red Sox vs. Orioles

Monday, May 27
1:35 p.m. ET
MLB.TV
Cooper Criswell Over 3.5 Strikeouts (+104)

By Tony Sartori

Right-hander Cooper Criswell takes the mound for Boston, and he should be a good candidate to back. Through eight appearances thus far, he is 2-1 with a commanding 2.86 ERA and 1.13 WHIP.

His underlying metrics suggest regression shouldn't be too big of a concern, as the right-hander ranks in the 70th percentile in xERA and 63rd percentile in xBA. Specifically, we are going to back Criswell in the strikeout market, as he ranks in the 74th percentile in chase rate and 60th percentile in strikeout rate.

Currently, you can find his strikeout prop at 3.5, with the over returning +104 at FanDuel. Criswell has surpassed this line in four of his past five appearances on the mound.

Pick: Cooper Criswell Over 3.5 Strikeouts (+104 | Play to -105)



Red Sox vs. Orioles

Monday, May 27
1:35 p.m. ET
MLB.TV
Red Sox ML (+140)

By Kenny Ducey

Cooper Criswell has run into a little trouble facing his old team over the past two outings, but it’s imperative not to ignore what this guy has accomplished this season under the wizard known as Red Sox pitching coach Andrew Bailey.

The righty has honed in his sinker, driving his ground-ball rate back up near 50% and pitching to a cool .230 Expected Batting Average on that delivery. He’s managed to come in above the league average in strikeouts and walks and profiles as an extremely reliable starter every five days.

Stepping into the hitter-friendly Camden Yards, Criswell’s ability to limit contact — and especially limit batted balls in the air — will be imperative. He’ll have the benefit, too, of dealing to an Orioles team that is hitting just .218 off ground-ball pitchers this year, amounting to a measly .546 OPS.

The Red Sox have been almost average when it comes to hitting lefties, with the 15th-best wRC+ in baseball within the split. While Cole Irvin has pitched to an above-average ground-ball rate, he’s coughed up a bevy of hard-hit balls and has been extremely ineffective in getting punchouts. That’ll hurt against a Red Sox team most hampered by the swing-and-miss, and I think Boston is live to win as a result.

Pick: Red Sox ML (+140 | Play to +130)



Cubs vs. Brewers

Monday, May 27
4:10 p.m. ET
MLB.TV
Brewers ML (-106)

By Tanner McGrath

The Cubs are slumping.

At best, the lineup is elite. But at worst, it’s among the most pathetic in baseball.

And the Cubbies are at their worst, posting a league-low 65 wRC+ over the past fortnight, a full seven points lower than the second-worst Nationals during the stretch.

The picture isn’t any prettier against southpaws; the Cubs have posted a league-low 64 wRC+ against lefties across the past month.

When you’re not hitting, you’re likely not winning, which explains Chicago’s 3-8 record over the past 11 games. The Cubs are in free fall.

And the free-falling Cubs will battle Milwaukee’s southpaw starter Robert Gasser, a young arm I’ve been rather interested in.

Part of the Josh Hader trade, Gasser gets by on a deep five-pitch arsenal headlined by a 16-inch glove-side-breaking sweeper with a 128 Stuff+ mark. He hasn’t generated many strikeouts across his first three MLB starts (six in 17 innings), but his chase rate is relatively high (31%) and his minor league strikeout numbers (30% in 28 Double- and Triple-A starts) indicate he has the whiff upside.

Of similar importance, Gasser’s batted-ball profile is near immaculate in his young career, where he ranks among the top three percent of pitchers in hard-hit rate allowed (20%), barrel rate allowed (2%) and average exit velocity allowed (85 mph). He was touched up for four earned runs against the Marlins, but they were all seeing-eye singles, given he induced a 53% ground-ball rate while allowing an 18% hard-contact rate.

There’s plenty to like about Gasser, and I think he’ll see some positive game-to-game ball-in-play regression in a good matchup against a slumping offense.

On the margins, I believe the Brewers have the better bullpen (eighth in bullpen fWAR to 16th) and defense (fifth in Outs Above Average to 27th), and they’re better on the basepaths (first in BsR to ninth).

Milwaukee is an excellent baseball team that does everything well, hence why I’ve bet them so regularly with so much success — the Brewers are the fifth-most profitable team on the ML this year.

It’s also worth mentioning the Cubs are still without two high-leverage relievers, Adbert Alzolay and Yency Almonte, both on the 15-day IL.

Cubs starting pitcher Justin Steele is always a scary prospect to fade, but he seems to be in a funk, as he’s allowed 15 earned runs over his past 16 innings. The Brewers have hit lefties hard over the past fortnight (.216 ISO) by elevating (32% fly-ball rate), which could be a problem for Steele given he’s forcing a lot fewer ground balls (career 50%, 41% through five starts this season).

For what it’s worth, the Cubs are winless in Steele’s five starts.

The Cubs are also in the dreaded post-Sunday Night Baseball spot. Playing on Monday after a Sunday night game is an awkward, unusual situational spot. The bats are generally a tad slower.

Pick: Brewers ML (-106 | Play to -120)

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