Caleb Wilfinger
The 2nd half of the 2025 MLB season continues rolling along, and Wednesday features a full slate of action for us to enjoy. I’m 71-51-1 on my MLB best bets this year and the Pickswise MLB handicapping team as a whole is currently on a 138-103-9 run! Let’s keep it going as we get into today’s top MLB predictions on Wednesday, August 27. You can also find out our MLB picks for EVERY GAME today.
MLB best bet: NY Yankees -1.5 over Washington Nationals (-120)
Odds available at bet365 Sportsbook at time of publishing. Playable to -130.
For my first MLB best bet for today, we’ll focus on this interleague matchup between the Nationals and Yankees. New York has been on cruise control in this series thus far, and the good times should continue with Max Fried on the mound in the Bronx. Fried has posted a 3.14 ERA this season and after a stretch where he surrendered 15 runs over 3 outings, the veteran left-hander was dominant over 6 scoreless innings against the Red Sox last week. Fried’s success in his last outing should translate into Wednesday’s contest at home, but I can’t say the same for Nationals starter Cade Cavalli, who has been noticeably worse away from the nation’s capital in his limited time on the mound this season. Let’s back the Yankees to win convincingly at home.
MLB best bet: Boston Red Sox ML over Baltimore Orioles (-145)
Odds available at bet365 Sportsbook at time of publishing. Playable to -160.
My 2nd MLB best bet on today’s slate takes us to Baltimore, where the Orioles are set to take on the Red Sox in the third installment of this 4-game series. The Red Sox are rolling of late, having won 5 of their last 6 games heading into this contest. Boston will also run out Brayan Bello to the mound, and that typically means good things for the Red Sox. After all, Bello holds a 3.07 ERA and he’s surrendered just 8 runs over his last 5 outings, including 7 shutout innings against the Yankees on the road last week. On the other side, the Red Sox offense has been rock solid of late and they’ll be facing off against Dietrich Enns and an Orioles bullpen that holds the 6th-worst ERA in baseball this season. Let’s back the visitors on the money line on Wednesday.
