Daily MLB Expert Picks & Baseball Predictions May 20

Josh Inglis - Betting Analyst at Covers.com
Josh Inglis • Betting Analyst 13+ years betting experience
Updated: May 20, 2026 , 12:29 PM ET • 4 min read

We're backing the Brewers and White Sox as underdogs tonight, along with an AL East Under, as our favorite MLB picks for Wednesday.

MLB expert picks May 20 Brice Turang
Photo By - Reuters Connect. Milwaukee Brewers second baseman Brice Turang (2) high fives catcher William Contreras (24) after hitting a two run home run against the Chicago Cubs.

Undervalued underdogs highlight our favorite MLB picks for Wednesday's schedule, as our baseball experts have found two moneyline plays that show a ton of value at Polymarket.

See why you should tail our baseball experts in backing the ChiSox and Brew Crew... as well as an Under in Jays/Yankees in a showdown between two aces.

MLB expert picks for today

Pick Odds
Josh Inglis Josh Inglis: CWS ML +133
Jon Metler Jon Metler: MIL ML +104
Joe Osborne Joe Osborne: TOR/NYY u8.5 -133

Prices courtesy of Polymarket.

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Josh Inglis' expert pick: White Sox moneyline

Price: 43¢ (+133) at Polymarket

The Chicago White Sox project as one of the best moneyline values on the board today at +133, with a fair price closer to -102. Years of losing have softened the market on Chicago, but THE BAT is extremely high on them in this spot. They grinded out a 2-1 win last night in Seattle, behind a combined one-hitter, and could catch a Mariners team looking ahead — Seattle has to pack up after a two-series homestand and travel to Kansas City for tomorrow, while the White Sox stay on the road and remain on the West Coast.

It’s a favorable schedule spot for Chicago, and Seattle could also be forced to navigate without its closer and setup man after both worked on back-to-back days.

Jon Metler's expert pick: Brewers moneyline

Price: 49¢ (+104) at Polymarket

The Milwaukee Brewers are trading as 49-cent underdogs in their NL Central matchup against the Chicago Cubs, but I make Milwaukee closer to 54-cent favorites in this spot.

Edward Cabrera draws a difficult matchup against a Brewers lineup that can stack as many as seven left-handed bats. That’s significant because Cabrera’s curveball loses some of its effectiveness against lefties, as it breaks into their barrels instead of away from them, but the bigger concern is command: Cabrera has always battled inconsistency in the strike zone, and this matchup could make him even more hesitant to attack hitters aggressively.

That’s dangerous against Milwaukee because the Brewers can pressure pitchers in multiple ways. They have speed throughout the lineup and can force mistakes on the bases, and Cabrera has historically been slow to the plate. If he starts handing out free passes, Milwaukee has the profile to capitalize quickly.

Joe Osborne's expert pick: Blue Jays/Yankees Under 8.5

Price: 57¢ (-133) at Polymarket

Everything points toward a low-scoring game tonight between the Toronto Blue Jays and New York Yankees. Both teams send dominant starters to the mound, with Cam Schlittler being the early AL Cy Young favorite after allowing one earned run or fewer in eight of his 10 starts this season, while Trey Yesavage has been nearly as sharp, bringing a 1.40 ERA into the matchup.

In 14 combined starts for Schlittler and Yesavage, only four have gone Over the game total. Both offenses have also struggled badly against right-handed pitching lately, ranking a surprising 26th and 28th in OPS over the last two weeks.


More MLB best bets for today

Pick Odds
Guardians ML -117
Read analysis in our Guardians vs. Tigers predictions
Royals ML -118
Read analysis in our Red Sox vs. Royals predictions
Diamondbacks ML -127
Read analysis in our Giants vs. Diamondbacks predictions
Reds ML +127
Read analysis in our Reds vs. Phillies predictions

Odds are correct at the time of publishing and are subject to change.
Not intended for use in MA.
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Josh Inglis - Covers
Betting Analyst

Josh Inglis is a rising star in the sports betting content space, specializing in MLB, NHL, and NFL markets. Since joining Covers in 2019, Josh has focused his betting expertise on player props and derivative markets, finding them easier for beating the closing line compared to sides and totals. His engaging analysis and content have been showcased on major networks such as TSN, VSiN, BetMGM Network, and NBC. Josh is a prolific bettor, tracking over 2,500 bets annually and he consistently shares his results through monthly transparency reports. At Covers, he is renowned for his MLB release shows and NHL Puck Props, which are integral parts of the site's live content lineup.

Before his tenure at Covers, Josh spent a decade teaching while pursuing sports media on the side. He has also contributed to live global senior-level broadcasts for the WBSC.

Josh advocates for sports bettors to bet early, emphasizing the importance of securing better numbers by beating the public to the market. He also advises having multiple sportsbook accounts to ensure access to the best possible odds.

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