MLB Expert Picks & Baseball Predictions May 27

Josh Inglis - Betting Analyst at Covers.com
Josh Inglis • Betting Analyst 13+ years betting experience
Updated: May 27, 2026 , 12:04 PM ET • 4 min read

Unders hit at a high rate when Shohei Ohtani pitches at Chavez Ravine, and we're going back to that well again tonight with our MLB expert picks for Wednesday.

MLB expert picks May 27 Shohei Ohtani
Photo By - Reuters Connect. Los Angeles Dodgers pitcher Shohei Ohtani (17) delivers a pitch during the first inning of a game.

We've got MLB picks for nearly every time slot on today's schedule, with a play at 4:10 p.m., 6:30 p.m., and late night at 10:10 p.m.

Read on to see why you should tail our baseball experts in backing the Phillies, Rays, and Shohei Ohtani. 

  • UPDATE: Added Neil Parker's best bet for CHW/MIN.

MLB expert picks for today

Pick Odds
Josh Inglis Josh Inglis: PHI -1.5 +122
Jon Metler Jon Metler: TB ML -108
Joe Osborne Joe Osborne: COL/LAD u8.5 -122
Neil Parker Neil Parker: CHW ML -104

Prices courtesy of Polymarket.

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Josh Inglis' expert pick: Phillies -1.5

Price: 45¢ (+122) at Polymarket

If I'm laying a run line, I want it with the road team... and one of the hottest pitchers in baseball, in Cristopher Sánchez. The left-hander hasn’t allowed a run in an absurd 37+ innings, and the Philadelphia Phillies have outscored opponents 21-2 over that stretch while going 3-1 ATS.

Another strong angle fading the Padres today, outside of facing Walker Buehler, is the schedule: The Friars are the only team making a cross-country trip for their next series, heading from San Diego to Washington to open a Friday set.

That 2,300-mile flight is one of the longest travel spots on the MLB board. It’s a strong getaway angle while also backing arguably the most in-form pitcher in baseball right now.

  • Time: 4:10 p.m. ET
  • How to watch: SDPA, NBCSP

Jon Metler's expert pick: Rays moneyline

Price: 52¢ (-108) at Polymarket

There haven’t been many bad spots to back the Tampa Bay Rays this season, but Wednesday sets up especially well. I price the Rays closer to 59-cent (-144) favorites against the Orioles.

At first glance, Baltimore’s lineup appears to have a platoon edge against left-hander Steven Matz, with right-handed power bats like Taylor Ward, Pete Alonso, and Tyler O'Neill near the top of the order. But Matz’s profile is built to counter that type of lineup; his sinking fastball and changeup work at the bottom of the zone, taking away the pull-side power those hitters rely on.

Meanwhile, Tampa Bay can stack seven left-handed bats against right-hander Trey Gibson, and those hitters benefit from the more favorable dimensions at Oriole Park at Camden Yards following the left-field wall changes.

  • Time: 6:35 p.m. ET
  • How to watch: FS1

Joe Osborne's expert pick: Rockies/Dodgers Under 8.5

Price: 55¢ (-122) at Polymarket

Shohei Ohtani has been nearly untouchable at Dodger Stadium, allowing one earned run or fewer in all 11 of his regular-season home starts since joining the team.

Overall, he owns a ridiculous 0.73 ERA across his eight starts this season, with seven of those games staying Under the total. He's also backed by a Los Angeles Dodgers bullpen carrying a 1.29 ERA over the last two weeks, while the Colorado Rockies rank dead last in wRC+ during that stretch.

Tomoyuki Sugano may look like an amateur compared to Ohtani, but his numbers are far more respectable away from Coors Field, and eight of his 10 starts have gone Under.

  • Time: 10:10 p.m. ET
  • How to watch: SNLA, COLR

Neil Parker's expert pick: White Sox moneyline

Price: 51¢ (-104) at Polymarket

The Chicago White Sox rank fifth in wOBA against left-handed starters this season and second in overall xwOBA while averaging 4.9 runs per game in May. Chicago righty Davis Martin is also dealing and sports an elite 2.04 ERA and 1.02 WHIP backed by a high-end 2.85 xFIP and 22.4 K-BB%. 

As a result, I give the edge to the White Sox on the mound and at the dish. The Minnesota Twins are countering with lefty Connor Prielipp, and in addition to him coming off his worst start of the season, the rookie’s 4.03 ERA and 4.34 xFIP are run-of-the-mill marks.

  • Time: 7:40 p.m. ET
  • How to watch: Twins.TV, CHSN

More MLB best bets for today

Pick Odds
Yankees ML -149
Read analysis in our Yankees vs. Royals predictions
Braves ML -108
Read analysis in our Braves vs. Red Sox predictions
Brewers ML -146
Read analysis in our Cardinals vs. Brewers 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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