MLB Expert Picks & Baseball Predictions May 29

Josh Inglis - Betting Analyst at Covers.com
Josh Inglis • Betting Analyst 13+ years betting experience
Updated: May 29, 2026 , 12:23 PM ET • 4 min read

We'll back Zack Wheeler at plus money, every single time, as the Phillies moneyline highlights our favorite MLB picks for Friday.

MLB expert picks May 29 Zack Wheeler
Photo By - Reuters Connect. Philadelphia Phillies starting pitcher Zack Wheeler (45) throws a pitch.

We're looking at even money (or better) plays for both of our favorite MLB picks heading into the final weekend of May.

Why should you back the Phillies tonight (vs. the Dodgers) and the Orioles against the Jays? Read on to find out!

MLB expert picks for today

Pick Odds
Josh Inglis Josh Inglis: BAL ML +100
Jon Metler Jon Metler: PHI ML +108

Prices courtesy of Polymarket.

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Josh Inglis' expert pick: Orioles moneyline

Price: 50¢ (+100) at Polymarket

The Jays have the pressure of getting back to .500 today, but they’re also extremely shorthanded on the mound. Toronto is rolling with a bullpen game and is likely without its three best relievers in Tyler Rogers, Jeff Hoffman, and closer Louis Varland, all of whom pitched on back-to-back days — and Toronto hasn’t had a day off all week. Triple-A call-up Austin Voth will likely be asked to cover innings, and he owns a career 4.70 ERA across 360 MLB innings with 61 home runs allowed. This grades out as one of the biggest +EV plays on the board today, per THE BAT projections, which have a fair price around -188 on this moneyline. Reliever availability is a massive edge that doesn’t appear to be fully priced into the current number

  • Time: 7:05 p.m. ET
  • How to watch: MASN, SN1

Jon Metler's expert pick: Phillies moneyline

Price: 48¢ (+108) at Polymarket

This one is pretty simple: If the market is giving me plus money on the Philadelphia Phillies with Zack Wheeler on the mound, I’m going to hit the button every time. The Phillies are trading around 48 cents on the moneyline, but I make them closer to 53-cent (-113) favorites in this matchup. The Dodgers are built around veteran hitters who excel at working counts, drawing walks, and capitalizing on mistakes for extra-base damage. The problem is: That approach doesn’t work nearly as well against Wheeler, who owns an elite 1.91 BB/9 this season and rarely gives lineups free opportunities on the bases. He forces teams to earn everything offensively, and he does it while pitching efficiently enough to work deep into games and limit exposure to the bullpen.

  • Time: 10:15 p.m. ET
  • How to watch: Apple TV

More MLB best bets for today

Pick Odds
Yankees -1.5 +108
Read analysis in our Yankees vs. A's predictions
Pirates ML -134
Read analysis in our Twins vs. Pirates 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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