MLB Expert Picks & Baseball Predictions May 25

Josh Inglis - Betting Analyst at Covers.com
Josh Inglis • Betting Analyst 13+ years betting experience
Updated: May 25, 2026 , 10:09 AM ET • 4 min read

Jump on the value the White Sox are showing against Zebby Matthews and the Twins, highlighting our best MLB picks for Memorial Day.

MLB expert picks May 25 Anthony Kay
Photo By - Reuters Connect. Chicago White Sox starting pitcher Anthony Kay (18) delivers a pitch at home.

We're celebrating Memorial Day with baseball all day — and a full buffet of MLB picks, based on prices from Polymarket.

Our MLB experts kick things off by backing the undervalued ChiSox, along with an Under play in San Diego... with more picks to come!

MLB expert picks for today

Pick Odds
Josh Inglis Josh Inglis: CWS ML +100
Joe Osborne Joe Osborne: PHI/SD u7.5 -108

Prices courtesy of Polymarket.

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Josh Inglis' expert pick: White Sox moneyline

Price: 50¢ (+100) at Polymarket

Why are the Twins road favorites today with Zebby Matthews on the mound? His run of good fortune is due to snap with a .227 BABIP while stranding 93% of his runners. He was getting tagged in Triple-A before the call-up and doesn’t profile as a good pitcher. He also threw 100 pitches in his last outing and hands things over to a bullpen that ranks 25th in ERA on the season and could be without Taylor Rogers after back-to-back appearances. Meanwhile, Anthony Kay is quietly putting together a strong season with two or fewer earned runs allowed in eight of his 10 starts. The Chicago White Sox still feel undervalued by the market, and THE BAT has this fair price sitting at -120.

  • Time: 2:10 p.m. ET
  • How to watch: CHSN/MNNT

Joe Osborne's expert pick: Phillies/Padres Under 7.5

Price: 52¢ (-108) at Polymarket

Jesus Luzardo has found his rhythm again, allowing two earned runs or fewer in five of his last six starts, and faces a San Diego Padres lineup that has struggled badly against left-handed pitching. Randy Vasquez has also been excellent with a 2.96 ERA, while the Philadelphia Phillies offense has been flat-out bad vs. righties... and on the road. The trends support the Under as well, with the Phillies cashing it in seven of their last eight games and San Diego doing the same in 10 of its last 12 at home. It also helps that the Padres' bullpen has been one of baseball’s sharper relief units lately and is well equipped to protect a low total.

  • Time: 6:40 p.m. ET
  • How to watch: SDPA/NBCSP

More MLB best bets for today

Pick Odds
Brewers ML -210
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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