Caleb Wilfinger
The second half of the 2025 MLB season continues rolling along today, and Monday features a full slate of action for us to enjoy. I’m 64-47 on my MLB best bets this year and the Pickswise MLB handicapping team as a whole is currently on a 126-98-8 run!
Let’s keep it going as we get into today’s top predictions on Monday, August 18. You can also find out our MLB picks for EVERY GAME today.
MLB best bet: Milwaukee Brewers ML over Chicago Cubs (+110)
Odds available at Caesars Sportsbook at time of publishing. Playable to +100.
Our first MLB best bet today takes us to Chicago for the first game of this NL Central double-header between the Brewers and Cubs. Milwaukee has been unstoppable over the last month, including putting together a 14-game winning streak over the span of multiple weeks that was broken up on Sunday with an extra inning loss to the Reds. The Brewers should be able to bounce back with Freddy Peralta (2.90 ERA, 9.5 strikeouts per 9 innings) on the mound in this contest against a Cubs lineup that has been trending downward of late. Milwaukee is facing Cade Horton, who has been excellent of late, but his expected metrics (4.03 xERA) do suggest that he’s due for some regression against a Brewers lineup that leads the league in runs per game on the road.
MLB best bet: Toronto Blue Jays ML over Pittsburgh Pirates (+100)
Odds available at BetMGM Sportsbook at time of publishing. Playable to -110.
For my second MLB best bet for today, we’ll focus on this interleague showdown between the Blue Jays and Pirates. Pittsburgh is sending Paul Skenes to the mound, which typically means good things for the otherwise lowly Pirates. After all, Skenes is one of the best arms in the game, posting a 2.13 ERA to go along with outstanding expected metrics across the board. However, the rest of the team is significantly worse than Toronto, as the Pittsburgh offense is ranked dead last in runs per game this season. That doesn’t bode well against Blue Jays starter Kevin Gausman (3.79 ERA), who has allowed 3 earned runs or fewer in 13 of his last 15 outings. I’ll back the much better team as a short underdog on Monday.
